Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Sudbury, Massachusetts: Once Upon a Time…

Upper Boston Post Road #10 (UPBR #10)

The Wayside Inn, Sudbury, Massachusetts.

One Autumn night, in Sudbury town,
Across the meadows bare and brown,
The windows of the wayside inn
Gleamed red with fire-light through the leaves
Of woodbine, hanging from the eaves
Their crimson curtains rent and thin.

Tales of a Wayside Inn
by Henry Wadsworth Longfellow


Once upon a time

Chapter One. The Youth’s Tale. Et in Arcadia Ego.

Halloween, 1981. The meadows across from the Wayside Inn, Sudbury, Massachusetts.

Listen, my children, and you shall hear of the midnight tale of a young rambler. On a chilly Saturday evening in October, four teenagers huddle on the grass under the stars discussing the bright future ahead, throwing ideas around, saying clever things, telling tales. Everyone is on the same wavelength, in tune with each other’s thoughts and with the magnificent setting, the light shining through the windows of the Inn across the road and the moonlight outlining our silhouettes. The world was our oyster and we declared then that we would reconvene annually in these fields, charting our progress through the years. The bonds of friendship seemed unbreakable and would surely stand the test of time. A year later we had all gone our separate ways, and I never saw any of them again.

A vibrant memory of an idyllic moment of intellectual and emotional maturation, a dream in which I am now one of the raconteurs in the parlor of Longfellow’s Wayside Inn, or a treatment for a screenplay? Is this something that happened to me or is it an amalgamation of Longfellow, Bildungsroman, Dead Poet’s Society, American Graffiti, The Return of the Secausus Seven, The Big Chill, or any combination of the seemingly limitless movies, books, and television shows that contain some variation on the coming of age story, of friends getting together to discuss the future or the past?

The meadows are real, did I dream the rest?

Yet the image of a younger version of myself bursting with ambition and camaraderie is uppermost in my thoughts as I make my way down the gravel pathway leading to the very real Wayside Inn and the meadows across from the Inn come into view. I arrive here as I continue my walk along the Upper Boston Post Road from Boston to Springfield, the subject of most of the recent entries in this project. In this entry, I walk across the town of Sudbury, Massachusetts from Wayland, where I left this road for a short while and wrote about an alternative road for a few entries.

Was it really over forty years since I was first here, talking about the future? In fact, I have been here before. This is an actual chapter in my life story as I remember it,1Since I have neither seen nor communicated with the other participants for over forty years I have only my recollection to confirm it happened and nobody to contradict my rosy view of the events of that evening. Perhaps the seed of the failure of our plans was already planted that evening. I will likely never know. One of the points of this entry is to address the trustworthiness of some of the stories of the Post Road. If I cannot with certainty say exactly what happened one night in 1981 when I was actually present, imagine how much more complicated it must be to piece together what happened in 1676 for example on a bridge in (then) Sudbury. and I happen to be revisiting the scene forty years later for reasons I would never have imagined all those years ago. I knew little to nothing then about the Wayside Inn; one of us lived nearby and we left a party to hang out together under the stars. I certainly had not read Tales of a Wayside Inn. Nor did I know then that the Wayside Inn would play an even greater role in other chapters in my life. So, on a warm, cloudless day at the end of May, the air heavy with the scents of spring, I felt like Charles Ryder in Brideshead Revisited as I strolled along the path to the Wayside Inn: “though I had been there so often, in so many moods, it was to that first visit that my heart returned on this, my latest”.2Brideshead Revisited, Evelyn Waugh, Boston: Little, Brown and Company,1945. p. 21. However gauzily bathed the details are in that moonlight, the story actually happened, as did all the stories below about my visits to the Wayside Inn.

Many narratives I encounter in the course of walking, researching, and writing this project are similarly bathed in a gauzy film of nostalgia, boosterism, and romanticism and are often entertaining and interesting, even if they can’t entirely be trusted. The same is also true of the artifacts encountered along the road, the old stone walls and the churches, the taverns and the milestones, which are sometimes not what they seem. The principal danger in this project is to not get trapped into believing everything I read in the local histories and see along the road of the towns I visit on my perambulations.3A very good example from the previous entry in this series is the milestone in front of the Wayland Historical Society. It is an authentic milestone and reads 19 miles, which is roughly the actual distance from the Old State House to the stone along the Upper Boston Post Road. However it was moved here from a spot along the Old Connecticut Path, another road to Worcester I recently spent a few entries writing about. Indeed, many narratives not just of towns, but of the Post Road itself (for example, Stewart H. Holbrook’s The Old Post Road from 1962 or Stephen Jenkins’ The Old Boston Post Road from 1913) are replete with fanciful anecdotes and stories whose details are not only frequently unsupported by evidence, they are all too often contradicted by simply walking the road itself. At times even Boston Post Road is not the Boston Post Road at all as we shall see. There is usually some kernel of fact in the narratives relating to the Boston Post Road, but one has to pull back the gauze and shine a light on some of the stories to see them more clearly, to tease out what is real and what is, to be charitable, wishful thinking. At least for this project, walking (preferably in the sunshine) has proven to be the best disinfectant.


Chapter Two. Invasions.

May 30, 2023. Old Town Bridge, Wayland, Massachusetts.

5.3 miles from the Wayside Inn.

View from Sudbury at a point just north of the Old Town Bridge across the Sudbury River looking towards Wayland on the opposite side. Notice the broad “water meadows” which made crossing the river a significant obstacle prior to the nineteenth century. Early bridges crossed at narrows in the northern and southern part of Wayland/Sudbury. The northern crossing, located today immediately behind the Wayland Country Club on Route 27 (Old Sudbury Road), was part of the original Upper Boston Post Road. In the nineteenth century a long straight causeway was built between Wayland and Sudbury, today’s Route 20 (Boston Post Road), shortening the travel distance by almost a mile. The upshot is that the Route 20 (Boston Post Road) crossing is NOT part of the ORIGINAL Boston Post Road despite its name.

To get to the Wayside Inn, at the western edge of Sudbury, one must cross the Sudbury River, the principal border between the towns of Wayland and Sudbury. As the original settlement of Sudbury comprised the land flanking both sides of the river, the early history of the contemporary town of Sudbury, on the west bank of the river, is naturally deeply intertwined with that of the town of Wayland, primarily on the east bank, as the two towns once comprised most of the original town of Sudbury. Although the Sudbury River serves as the principal boundary between the two towns, this is not true for large sections as we shall soon discover. However, the river effectively divided the original town into two sections, and the difficulty in the crossing of the river played no small role in the ultimate decision to separate into two towns.

As I discussed in my entry on the Upper Boston Post Road in Wayland, The oldest road used by travelers headed west from Boston crossed the Sudbury River at a point almost a mile north of the current crossing of “Boston Post Road,” the local name for US Route 20. Today’s straighter road across the river from Wayland into Sudbury was first built in the early 1800s and was widened and straightened with the advent of the automobile as a principal mode of travel from the 1920s to the present. However, although parts of Route 20 and the original route of the Upper (to distinguish it from another old Lower Post Road to New York from Boston through Rhode Island) Boston Post Road do overlap in Wayland, Sudbury, and other towns, the original road leading from Wayland to Sudbury followed a more tortuous path.

This road likely followed trails established by the various groups of people, such as the Massachusett and Nipmuc Indians who inhabited the territory prior to the arrival and settlement of Massachusetts by Europeans. These trails would have evolved for foot traffic and thus tended to avoid hills or swamps. River crossings were usually made at the most convenient and safe narrow section of the river. Early English travelers followed these paths and established roads along them and built bridges across rivers when possible. Unsurprisingly, given the vast expanse of marsh flanking either side of the Sudbury River, any crossing of the river would be a site of some importance in the Colonial Era.

Tales of a wayside bridge. Granite marker at Old Town Bridge in Wayland. The marker was erected by the Wayside Inn Chapter DAR (Daughters of the American Revolution), October 4, 1908.

A footbridge across a narrow section of the Sudbury River was built as early as 1641 at a spot just past what is today the Wayland Country Club.4Crossing the Sudbury, a short article available on the website of the Wayland Historical Society on the historic crossings of the river discusses this crossing in detail. The early crossing was at an oxbow in the river, where the geology forced the river into a curved narrow through areas of higher land. The bridge across the river led to a sort of peninsula in the middle of the marshes. The paper hypothesizes that at times of high water the river broke through the western edge of the peninsula and created an island. Alternatively a canal was cut through at some point creating an island. Regardless, by the eighteenth century there were in fact two bridges at this spot, the second bridge referred to as the Canal Bridge. The Canal bridge was washed away in the floods caused by Hurricane Diane in 1955 and was never rebuilt and an entirely new bridge across the river was built slightly to the south of the old bridges in 1955, today’s Route 27 bridge. A cart-bridge replaced the footbridge by 1643,5Alfred Sereno Hudson, The History of Sudbury, Massachusetts, 1638-1889. Published by the Town of Sudbury, pp. 93-96. and the dilapidated version in front of me was built by William Russell in 1848 and renovated in 1901. Nearby is a modern bridge across the river which was built after floods washed out the old bridges (there were two, the second bridge crossing a “canal” cut through on the other side of the Russell Bridge).6Again, I direct the reader interested in more detail to a short paper available at the Wayland Historical Society website entitled Crossing the Sudbury .

The Russell Bridge today sits at the end of a short road just beyond the entrance to the Wayland Country Club, a path that once was the Boston Post Road, but today leads to a defunct bridge covered in fallen limbs and overgrown vegetation. Near the bridge sits a large granite marker, erected on October 4, 1908 by the aptly-named (for this entry) Wayside Inn Chapter DAR (Daughters of the American Revolution).7This is the chapter for both Wayland and Sudbury according to the website for the DAR; However the Facebook page has not had an entry since 2018 and the website is a 404 Not found so the group may be currently defunct. The marker is inscribed on two sides with various “events” associated with the bridge, including the fact that Washington passed over the bridge. The event that catches my eye, however, is the short sentence “Over this the Indians were forced in King Philip’s Invasion.” This is the first time I have run into an artifact relating to King Philip’s War, an extremely violent and underappreciated event (June 1675-August 1676) in the early history of English contact with the Algonquian people who lived in New England when the first settlers arrived beginning in 1620. As I will relate shortly, what was considered a major victory over the forces of an Indian uprising led by King Philip occurred here, when the attacking forces were held at the bridge, thus limiting their advance toward Boston and turning the tide of battle.

The last incarnation of the bridge over the Sudbury River along the original route of the Upper Boston Post Road. This four-arch stone bridge was erected in 1848 and renovated in 1901 but fell into disuse when the flooding of the river in the 1950s resulted in the state redesigning the road and building a modern bridge a few yards south of the old bridge. Today the bridge sits almost unnoticed mere yards from the busy route 27 nearby. According to the Wayland Historical Society the bridge was once on the National Register of Historic Places but the listing was removed after the extent of reconstruction in 1901 was understood. Nevertheless it is a beautiful bridge.

I have a few problems with this story. First of all, how does one “invade” one’s own land? Second, although I admit I am a booster of the historical importance of the Boston Post Road, it was not the only route to Boston in this area, as my four recent entries on an alternate route west I have termed the Framingham Diversion discuss in some detail. Third, the “forcing” of the Indians across the bridge makes it seem that there was one big battle here that turned the tide of the “war” when in fact the story is significantly more complicated. Thirty five years earlier the bridge did not exist. Forty years earlier, the town of Sudbury did not exist and the land was lived on not by English settlers but by Algonquian-speaking people, no matter how ravaged the population may have been by disease in the years preceding the arrival of English settlers to Massachusetts.8The local literature does not discuss the presence of the native people in great detail. Hudson, in his History of Sudbury (pp.8-12) claims there were few people about when the English showed up but that their numbers had been higher a few years earlier. A map showing the geographical divide between the Massachusett and the Nipmucs is unsurprisingly vague, but the boundary between these two groups was likely somewhere in the vicinity of the Sudbury River, so one of these two groups is likely to have lived here before the arrival of English settlers in the late 1630s. A publication on the website of the Wayland Historical Society entitled Wayland Historical Tours does discuss the Nipmuc of Central Massachusetts and that the “few who were living in the Sudbury area when it was first established were friendly and cooperative.” (p. 21) This does not necessarily mean that the Nipmuc were the principal group living in Sudbury prior to 1638 when the first English settlers arrived, but there were Nipmuc people in the area in the days of early contact. The issue of who lived in Sudbury before the arrival of English settlers is addressed in more detail on Jan Hardenbergh’s website. The story of brave resistance to an invasion of the territory now called Wayland but known as Sudbury through the eighteenth century is just that, a story. Who is telling the story and what do they have to gain by it? Part of the answer is that “History is written by the victors” as the saying made famous by Churchill goes, but things are never quite as simple as that. I will revisit this question again as I make my way through the present-day town of Sudbury on the west bank of the Sudbury River and the subject of King Philip’s War will be a recurring topic as we move further west from Boston, where the war had an even more dramatic impact on the settlers and the earlier inhabitants of the territory along the Boston Post Road.


Chapter Three. The Newlywed’s Tale. The Chapel of Love.

February 26, 1989. Martha-Mary Chapel, grounds of the Wayside Inn, Sudbury, Massachusetts.

This quintessential New England scene is brought to you by Ford.

A light snow falls as a newly-married young couple exits the chapel surrounded by family and friends. The newlyweds pose awkwardly for photos in front of what appears to be a quintessential New England Meeting House, a simple white box with a pitched roof and wedding-cake steeple, perched on a rise overlooking the Wayside Inn (see photo), with the meadows across the road lightly covered in fresh snow. The bride’s beaming parents are partially responsible for the couple choosing this location as they had frequented the nearby Wayside Inn for years before this day, often bringing along their daughter and then boyfriend for a Sunday dinner on a crisp fall day or stopping on a drive in summer, meandering along the trails leading to the old Grist Mill or wandering through the very meadows where the boyfriend had spent a moonlit evening a few years earlier. They knew the place well and the young couple knew they would appreciate the choice of this venue, with it’s personal significance and iconic New England setting, for their wedding ceremony.

The scenery around the Wayside Inn gives the impression that the area was bypassed by modern times. In fact, the idyllic pastoral New England setting owes much to the vision and money of a man from Dearborn, Michigan, Henry Ford, and most of what we see today was created in the early twentieth century. The Martha-Mary Chapel for instance, site of the aforementioned wedding, was built only in 1940, and is named for the mothers of Henry Ford and his wife Clara. Ford, who had “retired” in 1918 from the Ford Motor Company as the world’s richest man9It is estimated that half of all the cars on American roads in 1918 were Fords!, began to pursue other interests, one of which was an interest in Americana. In 1923 he purchased not only the sixty acres of the Wayside Inn, but 1300 surrounding acres as well, and ultimately owned close to 3000 acres of property in the area around the Wayside Inn. He purchased the inn partly he said “as a small payment to Longfellow,” but also because he planned to turn the property into a historic village celebrating the “pioneer spirit” of early America.10Brian E. Plumb, A History of Longfellow’s Wayside Inn. Charleston, SC: The History Press,2011. pp. 103-104. Ford carried out some of this ambitious project, including the construction of the Chapel and the Grist Mill, but he divided his time between many other projects and by the end of World War II, with his health failing, he transferred ownership of the Inn and associated properties to a newly-created nonprofit Wayside Inn Trust, who scaled down the project to focus on the preservation of the inn, selling much of the land Ford had accumulated to pay the bills.

Ford’s influence on the landscape was profound; in an ironic act from the man who democratized driving in America with his reasonably affordable Model T, Ford even paid to move the main road, today’s US Route 20, also called Boston Post Road, slightly south away from the Wayside Inn, in order to preserve the pastoral feel of the setting and to preserve the buildings from the damage caused by the vibrations from traffic.11Plumb, p. 112. Brian Plumb summarizes Ford’s role well in his History of Longfellow’s Wayside Inn “If not for Ford, the inn would not be in the protected and tranquil setting it is in today…He is responsible for the preservation of the buildings and the landscape… he also built or rebuilt just about every structure …it is hard to imagine what the inn would be without his influence.”12Brian E. Plumb, A History of Longfellow’s Wayside Inn. Charleston, SC: The History Press, 2011. p. 96.

It turns out I have Henry Ford to thank for my youthful evening in the bucolic meadows surrounding the Wayside Inn, for the idyllic setting of my wedding, and for saving a lovely section of the Boston Post Road from the development that has engulfed so much of the area through which I walk on this project, mostly while being hounded by the incessant traffic which often seems to be comprised entirely of the ubiquitous contractors driving to and from their construction projects in, yes, Ford Trucks.


Chapter Four. Revolutions.

January 30, 2023. The Training Field, Sudbury, Massachusetts.

4.5 miles from the Wayside Inn.

Training Field, Sudbury.

The Sudbury River serves as the border between Wayland and Sudbury from a point just above the Old Town Bridge north all the way to the border with Concord (in the case of Sudbury) and Lincoln (in the case of Wayland), where the river also serves briefly as the border between the two towns to the north. South of the old river crossing the border between the two towns is complicated and confusing, befitting the messy divorce of the two parishes of the town of Sudbury in 1780.13The town had an earlier rancorous debate over the location of the meeting house; many of the residents on the west side of the river objected to the difficulties reaching Sunday services especially when the weather made crossing the bridge difficult and occasionally impossible. A petition as early as 1707 was accompanied by a map of the residences on both sides of the river as well as a statement written on the map; “The river in a flood is a half-mile over.” See the excellent presentation on Early Maps of Sudbury by Jan Hardenbergh video here (around minute 4-6 for the Brigham map, as well as his website for more maps of Sudbury. This problem was solved for a few decades by the creation of a second meeting house west of the river in what is now Sudbury center. By 1780 the population of the west side of the river exceeded that of the east side. However, the residents of the east side were wealthier and contributed more taxes to the town and complained that the money was being spent principally on the west side. Thus began the acrimonious divorce in which, in a rare occurence, the original settlement of Sudbury (which was on the east side of the river) lost the use of the name Sudbury and became East Sudbury (and eventually Wayland) in order to extricate themselves from the town. There was a big fight over the land flanking the river as well; hence the complicated border. This is discussed in Emery and in Hudson in great detail. The original road from the bridge, today called River Road, was built as a causeway, an elevated roadway through a low lying marshy area that followed the west bank of the river before climbing a hill on the west side that overlooks the wide expanse of water meadows flanking both banks of the river. River Road is in Wayland for almost a mile, as the border of Sudbury slowly creeps closer to the road, first along the west side of the road and then along both sides until, just before the road continues into Sudbury, only River Road itself is part of Wayland while the land on both sides of the road is entirely in Sudbury.

To make matters more confusing, there is a sudden protrusion of Sudbury into the wetlands of the river just as River Road becomes Old County Road as it enters Sudbury. This roughly diamond-shaped piece of land is bisected by Route 20, the road now known as Boston Post Road, before that road reenters Wayland briefly then reenters Sudbury for good 300 yards later. The curious border reflects the messy separation of the parochial towns of Sudbury and East Sudbury (later Wayland). Caleb Wheeler refused to allow his forty acre farm to be included as part of East Sudbury and so an exception was made to include his diamond-shaped property in the town of Sudbury.14Hudson, History of Sudbury, p. 513.

Detail of 1943 USGS Topographical map (Framingham Quadrangle) showing the south-eastern section of the town of Sudbury. This map gives a very clear sense of the complicated topography of the area through which the original Upper Boston Post Road passed in Sudbury, with a number of steep hills such as Goodman and Green Hill, as well as the wide wetland areas of the Sudbury River and Hop Brook. The original layout of the bridge over the Sudbury River is still present at top right (the curved red line). Also visible is the layout of the causeway from the bridge across the river meadows (River Road today), leading to Old County Road, which hugs the boundary between Wayland and Sudbury. The long straight US Route 20 (labeled Boston Post Road), the modern main crossing of the Sudbury River is visible at center right, as is the junction of Old County Road and US Route 20, where the old and new “Boston Post Roads” become one for a while, with the brief exception of the curved King Philip’s Road (originally part of the Post Road, at center just below the words “South Sudbury’). At the intersection of the railroad tracks (in the process today of becoming a rail trail) and Boston Post Road is the bridge across Hop Brook in the center of South Sudbury, once an important crossing. This map contains most of the principal areas of fighting in Sudbury during King Philip’s War in April 1676, with exception of the Haynes Garrison which is just off the northern corner of the map at right (near the red arrow).

The walk along River Road from the modern bridge of Route 27 adjacent to the Old Town Bridge to the Training Field is a lovely one. Regardless of which town the land technically belongs to, most of it is part of the Great Meadows National Wildlife Refuge. The initial few hundred yards still feel like a causeway, slightly elevated above the meadows, which at times close in on the road on both sides. On one winter walk through the area I encounter a flock of American Tree Sparrows working the grass on the edge of the causeway. On another walk in November a Northern Harrier flies six feet over my head as he drifts over the meadows hunting mice and other small mammals. Eventually the road rises and continues into a wooded area, before passing the Wayland Department of Public Works (DPW). The Wayland dump is just behind the DPW in this strange borderland and the Sudbury Transfer station is also located nearby in the diamond-shaped former Wheeler farm protrusion into Wayland. This feels either like a continuation of the contentious relations between the two sister towns or, more likely, a mutual disregard for the beauty and ecological value of the river meadows.

Map by Ensign Henry DeBerniere drawn in February 1775. The map is a bit confusing as the Sudbury River flows from south (at left) to north (at right) but the features of importance are all clearly labelled. The Training Field and the Powder House are on the hill described in the text to the left (east) of the “road to Marlbro,” which is today’s River Road, Old County Road, and Route 20/Boston Post Road, all part of the original Upper Boston Post Road. The “nineteen-mile tavern” may be the one listed as Goodenow’s or perhaps Burton’s or even Munn’s. It is unclear and I was unable to locate it on any other maps or references. Also, as it is more than 20 miles to the spot on the map where the tavern is marked from Boston, it might just be a mistake.

As the road levels out a small sign reading Training Field 1720 is visible on the left, behind which lies a simple field in the woods. A nearby board has information describing the history of the field, which served as a training area for the town militia, and some of the archaeological work that has been done there. Along the edges of the field are stones painted with dates in roughly five years increments. These mark the border between the two towns which are “walked” every five years, the year recorded on the stones, a process called a perambulation, which is a variation on my project!15 See Evelyn Wolfson and Dick Hoyt, Wayland A-Z: A Dictionary of Then and Now. (Saline, MI: McNaughton & Gunn, Inc, 2004), pp. 160-162, where they define perambulation as “Checking the location and condition of those markers that identify and designate the boundaries of cities and towns… By the 1830s, however, selectmen no longer used trees as boundary markers but referred instead to “stone” monuments. When the sand hill on route 20 was partially removed in the 1950s for sand and gravel, several stones were temporarily lost. On the bluff behind the Longfellow Club is one of the most handsome monuments, unusually large and beautifully cut and finished. It marks a corner of that particular piece of Sudbury that juts into Wayland like a hernia. Blame farmer Wheeler who didn’t want to live in East Sudbury… perambulation continues to be carried out every five years by two of the selectmen, or designates, from towns that share a common boundary: Sudbury, Natick, Framingham, Weston, and Lincoln. Usually one boundary is done at a time. Numerals are painted on the side of the monument indicating the year of the survey. Today some Wayland markers show as many as five dates.

The land on the hill east of River Road, site of the training field, was another source of contention as the inhabitants of the west side of the river wanted the land to remain in Sudbury arguing that another training field already existed on the east side. Hence, the curious border where the land comprising the former training field on the east side of River Road belongs to Sudbury for a few hundred yards north of the Wheeler farm “diamond.” Incidentally, the “Training Field” is labelled on the English spies Browne and DeBerniere’s map from 1775, as is a “Powder House” which was located a few yards away on the hill, along what the map referred to as the “Road to Marlbro.” The two spies, who were sent out by General Gage to look for and report on exactly things like powder houses and training fields, had a harrowing adventure along this road, which I have described a bit in the previous entries but will return to in more detail in the entry on Marlborough, the next town along the Upper Boston Post Road.

Although the training field was an important site in colonial Sudbury and likely served as a muster point for some of the Sudbury militia companies who marched to Concord on April 19, 1775, by the late-nineteenth century, according to A.S. Hudson in his History of Sudbury, things had changed: “the field was used as a training field in former years, and at one time a militia muster was held there. But now all trace even of the site has become obliterated, and for years it has been a quiet feeding place for cattle, and all is as peaceful there as if the slow pacing of the old Continental guard had never been heard at Sand Hill.”16Hudson, pp. 391-392. Indeed, even today there is precious little to see (not even cows, alas) except the aforementioned border stones and the information board. Yet it is an actual historic site in Sudbury and not a recreation like the more conspicuous Martha-Mary Chapel at the Wayside Inn. It is moving to stand in the field on a sunny day at the end of May, with Eastern Kingbirds and Baltimore Orioles singing in the trees, knowing that quite a few of the people who left here on that fateful day never came back. Appearances can be deceiving and sometimes the artifacts of true historical significance, like this field and the causeway leading to it, are like a glass of Muscadet; unadorned, not flashy but subtle, part of the meal but not the focal point.17I definitely thought of making a crack here about notes of stone but I resisted the temptation!

Detail of a map of Sudbury prepared in 1795 by Matthias Mosman showing the southern section of the town. The route of the “Post Road from Worcester to Boston” is visible crossing the town from “Caleb Wheeler farm” (the diamond-shaped area) at right to “Joseph Howe’s Grist Mill” at bottom left.

Leaving the Training Field I also leave Sudbury and reenter Wayland for a last few yards before I reach a sign indicating the border between the two towns, where River Road becomes Old County Road, a sidewalk appears, and commercial and residential developments appear on both sides of the road, something conspicuously absent along the walk through most of Wayland since leaving Boston Post Road/Route 20 more than two miles back. It can only mean one thing, that I am about to rejoin Boston Post Road/Route 20. The appearance of Herb Chambers BMW of Sudbury showroom confirms that my my brief escape along the tranquil winding section of the Upper Boston Post Road has come to an end.


Chapter Five. The Pilgrim’s Tale. Grist for the Mill.

Patriot’s Day, 2016. Grist Mill, grounds of the Wayside Inn, Sudbury, Massachusetts.

Grist Mill, Wayside Inn, Sudbury.

On April 19, 2011, I completed my first project, Walking the Post Road, when I published the the last entry of my walk from the Old State House in Boston to Battery Park at the southern tip of Manhattan along the old road through Rhode Island and along the Connecticut Coast known as the Lower Boston Post Road. In 65 entries I recorded my experiences as I walked 350 miles of road in four states. Two years later I completed a project I had been contemplating for almost thirty years when I followed the 500-mile course of the ancient pilgrimage route, the Camino Francés, from the French border near Roncesvalles in the Pyrenees across northern Spain to the Cathedral of Santiago de Compostela in Galicia.

Subsequently I started this project, Boston Rambles, as a way to keep walking but without having to invest so much time and energy into one long walk. The initial goal was to walk local roads that were easily accessible and to describe the evolution of the city of Boston through an understanding of its roads. The project also had a more open format in that I felt I could discuss politics, demographics, sports, and other topics which interested me and which I felt might be relevant to the city I call home, hence the double meaning of Boston Rambles. Of course the itch to wander off topic and eventually to wander off in general is part of my makeup and it wasn’t long before I could hear the siren call of the road (or perhaps it was just a police siren, hard to say).

One early spring day, five years after completing my walk to New York and while I was in the middle of researching and writing an entry about a walk through the nearby neighborhood of Roxbury, we took a drive along the route of the Upper Boston Post Road and stopped at the Wayside Inn. As we wandered the trails, we reached the lovely Grist Mill, a site we have visited and enjoyed many times before. In fact for decades we have always tried to have some corn flour or corn meal ground at the mill on hand in our house. As we watched the wheel turn I discussed my plans to revive the long dormant project of walking the Upper Boston Post Road.

In the course of researching my Post Road project I constantly ran up against the fact that most of the research on the “Boston Post Road” was principally, if not exclusively, focused on the Upper Boston Post Road, not the Lower Boston Post Road. Most of the lore surrounding the Boston Post Road focused primarily on the era of stagecoaches or on the visit of George Washington to various towns along the route during his famous 1789 journey. Very little was dedicated to the diaries of Sarah Kemble Knight or Alexander Hamilton, two earlier travelers who used the more commonly-traveled Lower Boston Post Road to make the journey between Boston and New York. I always knew that eventually I would have to follow the route of the Upper Boston Post Road. The problem is that I did not want to do it.

It was certainly not because I didn’t think the walk itself would be interesting; it was precisely because everybody else thought of the Upper Boston Post Road as the “real” or “interesting” or “romantic” road that I rebelled against giving satisfaction to that narrative by including myself as one of those who wallowed in the nostalgia of sleeping where Washington slept or of meandering through the same roads as the brave souls who fought for freedom against the British army and against the “savages” who tried to push them off their hard-earned farms. I just didn’t want to end up telling the same old stories.

Then, while working on my more local Boston Rambles entries I hit upon an idea that rekindled my interest in walking the long distance from Boston to New York along the Upper Boston Post Road: I would tell stories about the road myself but I would also try to look at the stories told about the road and, like one of my favorite writers Paul Theroux, cast a more skeptical eye on my subject. I would make the road itself the subject of the project, following the original road as closely as possible, documenting changes to the road and recording what the road is like now as I walk it, warts and all. This requires a different type of effort compared to my first Post Road project; I need to focus on a small section of the road at a time. Hence the entries are always focused on one town, in order to be able to understand the narratives at a more local level (and, incidentally, in keeping with the predominant form of political organization in New England since the earliest English settlements) and to be able to walk the road multiple times to understand the changes the road has undergone. I like to immerse myself in whatever town the road happens to be passing through, absorbing the local color, trying not to form opinions until I learn a bit about the lay of the land, much like Inspector Maigret in the Simenon novels, another favorite of mine.

The first project focused principally on what the travelers Knight, Hamilton, Washington, and others like James Birket saw as they passed through the towns and how much of this I could rediscover as a modern-day traveler along the same route. The current Post Road project is about the road itself and the stories the people living along the road tell about themselves. In order to make this project work smoothly and to make the narrative flow in a somewhat clear fashion, like my predecessors along this well-traveled road, I tell stories. For instance, the perceptive reader may have noticed while perusing an entry that the weather might differ from one photograph to the next, a winter landscape in one image followed by a maple tree resplendent in autumnal color followed by a field of spring wildflowers, despite the fact that the walk will be described as one jaunt across a town during the course of a single day. The “walk” in every entry in this project is actually a composite of multiple walks over a long period of time fashioned into a narrative generally focusing upon the most recent walk as the narrative device that literally moves the story forward.

There is no grand long-distance walk, no heroic journey from Boston to Springfield or New Haven or New York, despite the implication in the title. This walk through Sudbury, for instance, did not happen last week or when this entry was published. This walk began at least seven years ago, when I stood in front of the Grist Mill with my wife and I laid out my plans for walking the Upper Boston Post Road. In truth it began as soon as I finished walking the Lower Boston Post Road. It is the result of at least four complete walks through Sudbury and numerous other visits over the course of the last few years. In this and only this entry, as the theme of the entry is about telling tales, I record some of the dates that I actually undertook some of these walks in order to illustrate that they are indeed composite walks. I am not writing entries as I walk from one town to the next. There are drafts of multiple entries about a dozen towns sitting in my files waiting until I reach the next town along the road on this virtual journey. I am sorry to pull away the gauze from my own writing but in the spirit of this entry it seems incumbent on me to expose the fictional aspect of my narrative for what it is, a story. Having said that, although the dates and details of the walks might be compressed into a single “walk”, all the walks actually happened (multiple times in fact) and the details recorded in them are as accurate as my notes, voice memoes, photographs, and memories can be.

It is perhaps fitting to note here that the Grist Mill visible on Wood’s 1830 map of Sudbury (see below at far bottom left), is not the mill we see today (see photograph above), which is actually a reproduction of the earlier mill. The new mill was designed and built by John Blake Campbell, a Philadelphia hydraulic engineer and architect, as one of the first buildings in Henry Ford’s project, grinding its first cornmeal on Thanksgiving Day, 1929.18 Plumb, History of Longfellow’s Wayside Inn, pp.108-110. The millstones were imported from France, the design may have been based on mills around Campbell’s native Pennsylvania, and the location is about a hundred yards away from the original mill site. The setting is beautiful and, even if the mill is not actually the original mill from the colonial era, the cornmeal that it produces still tastes pretty good.

Incidentally, the fact that most of my recent entries have been about towns outside of Boston does not mean I won’t be writing any more entries on Boston topics or on sports or politics or whatever grabs my interest that might be tangentially connected to Boston. These will be interspersed among the Upper Boston Post Road (UBPR) entries as will more of my updated walks from my original project Walking the Post Road (WTPR). That is the point of the current structure of this project : I can do an entry on, say, Sudbury, along the Upper Boston Post Road, without having to give up more local walks.

Detail from an 1830 map of Sudbury by William Wood. This map is significantly more detailed than the 1795 Mosman map (see above). At the far right the diamond-shaped Wheeler Farm is shown with the relatively new “Worcester Road” cutting across it. A little further west the road intersects with the original Boston Post Road (Old County Road), which can be seen hugging the border with Wayland before it meets today’s Boston Post Road (US Route 20) at the “Haman Hunt House”. A little further west along “The Post Road From Boston to Worcester”, a new straighter road (built after Mosman’s 1795 map) cuts off a crescent-shaped road, originally called Crescent Street, today King Philip’s Road, part of the original post road west on Mosman’s map. Another cutoff just west of “Larnum Brook” (today’s Hop Brook) is also visible: the crescent on the map no longer exists but small segments remain in today’s Maple Street and Raymond Road as explained in the main text. Further west is “William Stone’s Tavern”, “Adam Howe’s Hotel”(The Wayside Inn), and “B. Howe’s Grist Mill.”


Chapter Six. Wars.

May 30, 2023. Junction of US Route 20 (Boston Post Road) and Old County Road, Sudbury, Massachusetts.

Crazy man on the side of the Boston Post Road.

4.0 miles from the Wayside Inn.

A person entering Sudbury along US Route 20 from Wayland would be forgiven for thinking they were following the old Boston Post Road. After all the road is actually called Boston Post Road. The 1.5 mile section of Route 20 from the Weston border with Wayland to the junction with Route 27 in Wayland Center is a part of the original road. However, the subsequent 1.8 miles section of Boston Post Road (US Route 20) from Wayland Center across the Sudbury River is NOT the original road and was only created in the early nineteenth century, and was certainly not called Boston Post Road until well into the twentieth century.

The spot where I am currently standing, at the intersection of Old County Road and Boston Post Road (US Route 20) in Sudbury, is part of the original road. This busy junction is where the original Upper Boston Post Road rejoins the eponymous road for most of the next four miles across the town of Sudbury before I reach Wayside Inn Road. Only then, with one short but important exception, will I finally rediscover the tranquility I encountered along the section of Old County Road and River Road that I have just finished walking. Fortunately, despite the development, the traffic, and the noise, there are still historical nuggets to be found as I walk along.

A mere two hundred yards from the Herb Chambers showroom I encounter the first of these nuggets, a plaque describing the Goodenow Garrison House (see photo below), one of a handful of fortified buildings established by the English settlers on this side of the river to which residents would seek refuge in the case of attack. This building, which according to Hudson had ceased to exist at least 75 years before his History of Sudbury was published in 1889, was reputed to be located at a site close to the sign along Boston Post Road. The sign itself is an interesting historic artifact as it is one of many such markers placed around Massachusetts in 1930 to celebrate the tercentenary of the establishment of the Massachusetts Bay Colony and so is close to a century old.

Plaque indicating site of Goodenow Garrison House, Boston Post Road (Route 20), Sudbury. Ahead at left is the turnoff for Old County Road which is part of the original road, diverging from Boston Post Road (Route 20).

A similar sign, this one for the Haynes Garrison house can be found a little west of the Old Town Bridge, near Water Row on the road into what is now Sudbury Center. This and the other garrison houses, all located within the current town of Sudbury on the west side of the Sudbury River, played an important role in the violence that occurred during King Philip’s War. It should be noted that almost all the fighting and virtually all the destruction of property occurred on the west bank of the Sudbury River. Whatever role the bridge may have played, most of the action in the war occurred not in Wayland but in Sudbury and places further west which were substantially less populated and more directly in Nipmuc territory, which may at least in part explain why the war never reached particularly close to Boston.

As I walk along Boston Post Road, with the seemingly endless traffic zooming past, I encounter some new commercial development that was not here on a previous walk along with a lot of commercial and residential development that was here on previous walks. After ten minutes of walking I reach Landham Road, an old road to Framingham clearly visible on Matthias Mosman’s 1795 map of Sudbury and labelled as the “Road to Framingham” on William Wood’s 1830 map of Sudbury (see above). A four-foot tall rectangular granite stone sits at this junction, with hand-painted names and arrows showing the direction of various nearby towns, as well as indicating the direction of the Wayside Inn. I am absolutely certain that this is not as old as it appears to be and, lacking any specific evidence, hazard that the stone likely has some connection to Henry Ford’s project at the Wayside Inn.

A little further along, as I begin to tire of the noise and development and little of interest, the road crosses a small brook and I first pass what is clearly a very old house built at a 45 degree angle to, and far back from, the road. The next property has an ivy-covered fence facing the road that is draped in an American flag and a plaque reading 01776, a reminder of Sudbury’s interesting zip code. Contrary to rumors that Sudbury won it in a bar bet between local postmasters, apparently the coveted zip code is merely the fortunate result of a random assignation.19See this for instance Just beyond the flag-draped fence a sign tells me I have entered the King Philip Historic District, after which the road heads slightly uphill before I reach King Philip Road, a brief (0.3 miles) deviation of the old Upper Boston Post Road away from busy Route 20/ Boston Post Road.

On Matthias Mosman’s survey of Sudbury (see above), prepared in 1795 as required of each town by the state in order to create an accurate map of Massachusetts (Osgood Carleton’s 1801 map of Massachusetts being the final product), there is a clear curve along the road labeled Post Road from Worcester as it nears the County Road from Framingham. The county road is today’s Nobscot Road and Concord Road as we shall see shortly. The curved section of the Post Road is today called King Philip Road, and this was originally the main road until sometime in the early 1800s when the straighter section of Boston Post Road was built that is visible on William Wood’s 1830 map of Sudbury (see above). On a 1908 map of Sudbury the road is called Crescent Street but by 1938 it had acquired the name King Philip Road on a survey map of the town.

The gentle curve of this quiet road is a relief from the incessant drone of traffic. In truth I was only on Route 20 for less than 20 minutes but it felt like much longer. The whole feel of the walk changes on these strolls along forgotten segments of the old road and not just because of the traffic. There is almost always less modern development along these “back roads” and there is often much more historical evidence on the ground, particularly in the form of old houses. The very first house along King Philip Road is obviously at least two centuries old and has a lovely red barn on the property that the Sudbury Historic Inventory reports as dating to 1729. Many other interesting buildings from the eighteenth and nineteenth century line the shady road for the all-too brief third of a mile length, before rejoining the main road.

Gideon Richardson House 1790 (according to Sudbury Inventory of Historic Buildings) at 38 King Philip Road in Sudbury. This short curved road, once called Crescent Street, was part of the original Upper Boston Post Road, as evidenced by the date of this and several other nearby houses.

How and why did King Philip Road acquire it’s name? In order to understand what might have led to the new name of the road and of the subsequent historic district we need to look back at the events of 1675-1676. At the time the town of Sudbury was close to the frontier of English settlement, with only the settlement of Marlborough directly to the west, and the settlers on the west side of the Sudbury river in 1675 were far fewer in number than the population of the original settlement in what is now Wayland.20Marlborough had about 225 residents in 1675, while settlements further west were essentially in the wilderness: Worcester had about 6 families, Brookfield had twenty families. There were substantially larger settlements along the Connecticut River such as Springfield and Northampton, but along the road west of Boston, the number of people settled in the area west of the Sudbury River was certainly under 1,000 settlers. See Eric B. Schultz and Michael J. Tougias: King Philip’s War: The History and legacy of America’s Forgotten Conflict. Woodstock, VT. Countryman Pres, p. 20. Despite the dramatic demographic catastrophe of the preceding sixty years among the Algonquian peoples of New England as a result of disease and other factors likely connected to contact with Europeans, there were still thousands of people living in the areas increasingly encroached upon by the burgeoning English population. As Eric Schultz and Michael Tougias put it in King Philip’s War “while the impact of disease, trade, firearms, religion, and alcohol were all important in defining the English-native relationship, it is impossible to escape the fact that New England Indians were victims of colonial Americans’ inexhaustible appetite for territory and expansion.”21Eric B. Schultz and Michael J. Tougias: King Philip’s War: The History and Legacy of America’s Forgotten Conflict. Woodstock, VT. Countryman Press, p. 18. King Philip, the son of Massasoit, the sachem of the Wampanoag, an Algonquian-speaking people who lived in what is today southeastern Massachusetts and parts of Rhode Island, led an uprising in alliance with among others, the Nipmuc people of central Massachusetts, against continuing encroachment upon Indian territory in the spring of 1675, resulting in a vicious conflict which cost more lives per capita than any subsequent war on American soil.22Schultz and Tougias, p. 5. It is believed 800 English settlers died out of an estimated population of 52,000 (nearly 2% of the entire population), while over 3,000 of an estimated Native American population of 20,000 died, a staggering 15% of the entire population already decimated by decades of disease. By comparison, about 0.34% of the US population has died from COVID since it began 3.5 years ago (1.14 million of 335 million Americans) and about 0.9% of the US Population died during the Civil War (305,235 of 35,630,885).

Sudbury was the scene of a major conflict in April, 1676. The fiercest fighting took place on nearby Green Hill, a quarter mile to the north of King Philip Road, resulting in the deaths of dozens of English soldiers, although ultimately the Indians retreated, possibly realizing they were at a numerical disadvantage as reinforcements arrived from towns closer to Boston.23Schultz and Tougias, p. 219. The authors also include a much more detailed description of the action in Sudbury, pp. 210-220. Whatever the reason, this was as close to Boston as King Philip’s soldiers would get and within months Philip himself would be killed, effectively ending the war.

Attitudes towards Philip and towards American Indians waxed and waned over the course of the subsequent three centuries. The minister Cotton Mather spoke of Philip as a “blasphemous leviathan.”24Jill Lepore, The Name of War: King Philip’s War and the Origin of American Identity. New Yorl: Knopf, 1998. p. 174. and the native inhabitants of America continued to be “merciless Indian savages” even in the Declaration of Independence. By the early-nineteenth century Philip and his reputation began to change. Washington Irving wrote an essay in 1814 entitled “Philip of Pokanoket” in which Philip is portrayed as “a true born prince, gallantly fighting at the head of his subjects …to deliver his native land from the oppression of usurping strangers.”25Quoted in Lepore, p.196. An extremely popular play about Philip called Metamora, was particularly well-received in New England in the mid-nineteenth century, where many were sympathetic with the Cherokee protest at their removal from lands in what are now Georgia and Alabama.26Lepore, p. 205. Lydia Maria Child, whose house in Wayland sits less than a mile from Old Town Bridge, was an ardent advocate of Indian rights.27Lepore, ibid. The end of the Civil War and the end of slavery, along with continued westward expansion and a resurgence of conflict with Indians led to the Indians once again becoming a “nuisance” and a “problem” and to concomitant “hatred of Indians freed from restraints.”28Lepore, pp. 224-225. By the 1920s, with the last Indian tribes safely ensconced in reservations, a resurgence of appreciation for the vanquished enemy and a nostalgia for colonial heritage once again raised Philip’s profile.

Perhaps in reaction to large numbers of immigrants, perhaps a reaction to rapid modernization, or perhaps for another reason as yet undiscovered, in the 1920s a fashion for the colonial American past resulted in a virtual cottage industry in early American cultural artifacts, of which the Wayside Inn was one manifestation. The energy emanating from Henry Ford’s project spread far beyond the borders of the property; Ford also purchased Noyes’ mill on nearby Hop Brook, an important building during the Sudbury fight,29Schultz and Tougias, p. 216. and is likely to have played some role in the placing of “old” milestones along a newly renamed Boston Post Road. The fever for colonial connections certainly played a role in the renaming of King Philip’s Road, the former Crescent Street, an early section of the actual Boston Post Road long ago left behind by the modern straighter road, but ultimately the better for it.


Chapter Seven. The Veteran’s Tale. Decades of Experience.

February 26, 2019. Tap Room of Wayside Inn, Sudbury, Massachusetts.

Tap Room of the Wayside Inn

Of all the visits to the Wayside Inn a trip in February 2019 ranks as my favorite. I walked over to Brookline Village and took the Green Line D Branch train to Newton Centre, where my wife boarded and we continued on to Woodland Station. From there we took the Route #1 bus of the MetroWest Regional Transit Authority to Natick Mall, where we transferred to the Route #3 bus, which took us to the Nobscot Shopping Center in North Framingham. From there we walked north along Edgell Road into Sudbury where the road changed to Nobscot Road (the old Road to Framingham on Wood’s 1830 map of Sudbury), until we reached Dudley Road, which we then followed until we reached Boston Post Road. From the junction of Boston Post Road at Dudley Road we walked west along the route of the Upper Boston Post Road until we reached the Wayside Inn; the total walking distance was a little under 5 miles and took us about two hours while the total travel time from Newton Centre to the Wayside Inn was about four hours.

Most likely the reader is shaking his or her head at this point in bewilderment; why would someone take a four hour journey on a train and two buses plus a five-mile walk for a trip that takes 40 minutes by car? If you have been reading any of my previous entries you will know the answer. Regardless, for us the journey was half the fun and the other half was being able to spend our thirtieth anniversary at the Wayside Inn on a cold winter’s night. It was a quiet evening and the restaurant had only a few customers, so we were able to take our time and savor the atmosphere of the charming room known as the Old Kitchen. Then we meandered the halls, perusing all the old photographs, exhibits, and documents, poking into the unused dining rooms, the ballroom, the parlor where Longfellow set his Tales of a Wayside Inn, the sitting rooms, and chatting with the friendly staff, before settling into our historic room with uneven wide-plank floors and low ceilings. The next morning we had a massive breakfast to follow our robust dinner. Our friendly server Marina was a fount of entertaining anecdotes in no small part because, as she told me on my most recent visit in May, she has worked at the Wayside Inn for 47 years. The longevity of many of the staff is a sign of a decent and well-run establishment. She said with justifiable assurance that she would very likely have known my wife’s parents who frequented the Wayside Inn regularly.

One of the many interesting displays on the walls of the Wayside Inn. This panel recounts the acquisition of the famous Sign of the Red Horse by Henry Ford in 1929.

Although many of the staff, like Marina, have employment records of astounding longevity, the Wayside Inn itself has had a more fitful and discontinuous history. There has not been an inn here for the entirety of the 321 year history of the property; indeed it was not a functioning inn when Longfellow visited and published his Tales of a Wayside Inn in 1863. Nevertheless, according to Brian Plumb (in his History of Longfellow’s Wayside Inn, with my own updates to the numbers he calculated in 2011), a tavern has stood on the site for 307 years and it has operated as such for 271 of those years.30Plumb, p. 13.Pretty astonishing numbers when you actually stop and reflect on them! The slightly disheveled history of the inn is part and parcel of what makes an old place authentic; it is almost unheard of for any place to remain completely intact for centuries. The highs and lows of the Wayside Inn, the fires that gutted parts of the building, the renovations, the additions, the conversion to a private home, the return of the inn and the attempts to restore the inn and its surroundings to a more “colonial” setting are merely the slings and arrows of outrageous fortune that “this ancient hostelry” has suffered and are part of what gives the Wayside Inn its rich character.

The house that became the Wayside Inn was built by David How sometime around 1702. In 1716 the selectmen of the town of Sudbury gave their approval to How’s petition to establish a “hous of entertainment for travelers.”31Plumb, p. 29. Four generations of the How (later Howe) family continued the inn-keeping tradition until 1861. After a period as a private home, where occasional tours would be given by the residents (see Chapter 9 below), the inn-keeping tradition was reestablished in 1897, and the inn was purchased by Henry Ford in 1923. Both sets of modern owners made substantial alterations to the building, but these were minor compared to the damage caused by a massive fire on the night of December 21, 1955, which destroyed large sections of the building and caused significant damage to the rest of the structure. The opportunity to rebuild the inn with professional expertise in a late-colonial style resulted for the most part in the building we see today, a 1950s rebuild of an eighteenth century inn.32Plumb, pp. 130-133.

The famous sign of the Red Horse. Like every aspect of this project, the sign has a complicated history. “Legend” claims the name was changed by Ezekiel Howe in 1746, but little evidence exists to assess the claim. Most of the references documented by visitors, such as Thoreau in 1853, refer to it as “Howe’s Tavern.” The one that matters most for the subsequent history of the inn is Longfellow’s 1863 reference “The Red Horse prances on the sign” in his Prelude to Tales of a Wayside Inn.

One of the banners on the Wayside Inn website says “Dine and stay where history is made” which, read in a certain way, unfortunately can sound a bit ironic. Is history being made here as in constructed for purpose or is it a place where many events of historical significance have occurred? Not for the first time in this project I am confronted with the question of authenticity. Is this inn real or is it a Disney-style recreation? In so far as it is impossible to recreate a building that has been transformed over three centuries from a simple house in the wilderness into a large inn with a ballroom that was the centerpiece of a planned colonial-era working village, it is not an easy question to answer, particularly after the fire that devastated the building. Which “style” is most representative of the “real” inn? For many reasons, not least of which is Longfellow’s impact, they settled on a style that happens to dovetail with my interests in this project, which is to trace the colonial roots of the Boston Post Road as closely as possible. I know it’s not truly “real” but I appreciate the effort that went into attempting to be authentic.33I once worked at the Charlestown Navy Yard, home of the USS Constitution which purports to be the oldest active commissioned naval vessel. The joke among the rangers was that only about three toothpicks worth of original wood remained in the ship. Yet it is those “three toothpicks” that provide some form of continuity and keep the claim alive. There are surely more than three toothpicks worth of original material left in the Wayside Inn.

It is also begs the question when does history begin? One could argue that the colonial emphasis is irrelevant as we know relatively little about the inn in the colonial era, that the Longfellow connection is the most important aspect of the history, that the Ford era is now of significant historical interest. When you layer over all this the accumulated knowledge of people like Marina, who is a treasure in her own right, and add the personal stories of the visitors over the years who in some cases have deep connections to the place, the question of authenticity becomes even more difficult to answer. My interest in the Post Road is a direct attempt to address the question of authenticity and truth, but I don’t have all the answers. In the case of the Wayside Inn, I would argue that something can be inauthentic and real at the same time.

After our hearty breakfast, we walked around Carding Mill Pond and strolled the paths of the property for a while before we took leave reluctantly of the Wayside Inn and headed east on the Post Road, toward Boston. As we made frequent stops to explore places of interest along the road (and to warm up on a cold day), we managed to get only as far as Weston before darkness ended our pedestrian adventure after ten miles, and we took an Uber to Riverside train station to finish the trip home. This story would have been so much more satisfying if we had walked all the way home and of course we were disappointed that we did not manage at least to get back into range of the MBTA’s network. Seen another way, it is almost fitting that the story does not have a harmonious and neat ending, much like the patchy history of the Wayside Inn itself. Yet I am serious when I say that I had more fun on that trip, slow buses and trains and snow-covered sidewalks and busy traffic roaring past and not finishing the walk before dark and taking an Uber(!) and all, than on some trips abroad I have taken; it’s all about perspective and how and with whom you spend your time. I wouldn’t trade those memories for the world.


Chapter Eight. Travels.

February 27, 2019. Goodnow Library, Sudbury, Massachusetts.

2.8 miles from the Wayside Inn.

Not a real milestone.

At the end of King Philip Road I find myself back on the bustling Boston Post Road, which is lined on both sides with shops and offices for the two hundred yards leading to the intersection with Concord Road. Four years earlier, on a cold winter’s day in February, I might have passed myself walking with my wife from the Wayside Inn after having spent the previous evening celebrating our thirtieth wedding anniversary. On this day in late May, however, it is very hot and sunny as I reach the very busy intersection at the heart of South Sudbury, an area that was called Mill Village on Walling’s map of the area as late as 1856, but appears as South Sudbury on Walker’s map of 1889. The stone marker I mentioned at the junction with Landham Road which indicated the direction of “So. Sudbury” is beginning to look even less authentic, as does the one here at the intersection of Concord and Boston Post Road, which prominently lists the “Wayside Inn” as a destination, something it certainly was not called before Longfellow published his book in 1863. Yet these stones are listed in the Historic Inventory of Sudbury as being “1767 Milestones,” and it turns out that they were included in 1971 in the forty or so stones in Massachusetts listed on the National Register of Historic Places as part of a series of 1767 milestones.

It is my contention that these purported milestones in Sudbury are not actual milestones as is claimed and that they have not been here since 1767. For one thing there are no mileage numbers inscribed on them or signatures, just stenciled labels painted directly on the stone. They appear to be made of granite and to have the characteristic marks left by tapping the stone to split a larger piece of granite more typically found in quarried granite, like the stones used for the Bunker Hill Monument in the early nineteenth century, when large scale granite quarrying began in New England. In addition to being a difficult stone to quarry and transport, granite is a much harder stone to carve and to inscribe. Finally, most of the authentic milestones I have encountered are typically not carved but rather appear to be composed of large individual stones, likely from nearby, dragged to the road side where the mileage is typically inscribed on site, along with the initials of the person responsible for the stone. In short, these stones have none of the usual characteristics associated with Boston-area milestones of the eighteenth century.

A much more likely scenario is that they were placed here sometime after Henry Ford began his Wayside Inn project in the 1920s and were meant to give an antiquated feel to the drive from Boston to the Wayside Inn. There are no stones like this in the neighboring town of Marlborough to the west of Sudbury, for example. Even the very box-like appearance of these stones is unlike the shape of any stone I have thus far encountered on my walks. They more closely resemble a plinth for a statue than a milestone. The notion that these are eighteenth-century milestones has been perpetuated and has even been deemed the official story by both the town government and the Federal government despite the many obvious problems with this narrative; so many problems that this subject is best dealt with directly in more detail in a forthcoming entry dedicated solely to a history of the milestones along the Upper Boston Post Road.

A short walk from the “milestone” at the junction of Boston Post Road and Concord Road (which was called “Centre Street” on the 1908 map) is the Goodnow Library, a lovely old redbrick library with a tastefully hidden modern section attached to the rear of the building. I stopped here on our winter walk from the Wayside Inn to Weston in February 2019 and I stop again on a hot day in May 2023. Both times the library served as a pleasant place to rest and either warm up or cool off, as well as a place to research the history of the road. Of great interest to me along the walls of a section of the old library are paintings of historic landscapes and buildings of Sudbury, including the Haynes Garrison House near the Old Town Bridge, the Government Storehouse on Sand Hill (the “Powder house” on Deberniere’s map located near the training field), and the Wayside Inn as it looked in the early nineteenth century. These paintings are the work of Alfred Sereno Hudson, author of The History of Sudbury, one of the sources for the history of the town I have used for my research, published in 1889. The paintings were done in 1883/1884 although most of the buildings were long gone; even the painting of the Wayside Inn contained elements which were not present on the incarnation that existed in Hudson’s day. In other words, they were imaginative recreations of Hudson’s based on whatever evidence he had collected from his research. The line between reality and historical memory is very thin indeed in this town and indeed in almost all the towns along the route of the Post Road. Longfellow’s influence on the town has been strong.

Hop Brook, one of the simple pleasures of walking the road rather than driving.

I retrace my steps from the library to continue my walk along Boston Post Road, passing another of the 1930 historical plaques. This one is a brief recapitulation of the Sudbury Fight on Green Hill in 1676, the third tercentenary marker I have encountered thus far; all concern King Philip’s War, in keeping with my hypothesis that the transformation of Crescent Street to King Philip Road was part of the same Colonial Revival movement. Boston Post Road in the area around South Sudbury was called Main Street on a map of the area from 1908; the road east was called the Boston Road and the road west was called the Worcester Road. The name of the entire length of US Route 20 was changed to Boston Post Road sometime between 1908 and 1938, likely along with the placement of the granite plinths in search of statues and the appearance of the tercentenary plaques celebrating the victory over King Philip.

Despite still being within the bounds of the King Philip Historic District, there are an awful lot of modern uninteresting commercial buildings along Boston Post Road in this section of South Sudbury. A few yards past the faux milestone the road passes over a small but lively brook, a brook I would even characterize as babbling were it not for the noise of the traffic, a brook likely unnoticed by the drivers of the many vehicles passing through this busy area. Hop Brook is clearly labelled on Mosman’s map of 1795, conveniently clarifying a map that does not have many notations. Immediately beyond the brook a sign tells me I am entering George Pitts Tavern Historic District and I cross the path of the former railroad, now in the process of being developed as a rail trail for bikes and pedestrians.

Today Boston Post Road follows a direct line west from this point, but on Mosman’s 1795 map of Sudbury there is clearly a curve south in the road after it crosses Hop Brook, a curve which includes the both the “County Road to Framingham” and the “Post Road from Boston to Worcester,” the two roads being the same from the intersection with Concord Road to a point near today’s Nobscot Road. This curve is also visible on Wood’s 1830 map, which also shows the more direct cutoff road of today, similar to the one that cuts off what is now King Philip Road. By 1856 the curved part of the old road west of Hop Brook, unlike King Philip Road, no longer appears on maps of the area and the cutoff road had become the sole road. This is very apparent on the much more detailed map of South Sudbury of 1889 and 1908, which show individual buildings but no longer show the curved section of the old road.

The stately Christopher Cutler house from 1800 house at #7 Maple Road, a short road leading south from Boston Post Road just beyond Hop Brook, provides a clue to the likely route of the old road. According to Alfred Hudson “the C. G. Cutler place was the old George Pitts place. A building formerly stood south of the present one, near which the old road passed. It was once used for a tavern, and was probably kept by George Pitts, at whose house one of the early meetings was held to consider the matter of having preaching on the West Side.”34Hudson, p. 493. The Cutler house is shown on Walker’s maps of South Sudbury from 1889 and 1908, but the roads have been transformed into something like their current form.

C.G. Cutler House from 1800 along Maple Avenue in South Sudbury. This stretch of road is likely the old route of the Upper Boston Post Road. The road would have curved to the right in two-hundred yards; part of nearby Raymond Road also has a few yards of the original road while most of the rest now seems to be in the woods behind the Sudbury Crossing Shopping Center. See black line on map at the bottom of this entry

I have created a map which follows the route of the Post Road through Sudbury (see the bottom of this entry). The red line is the route of the road that can be followed today while the black line is a recreation of the route of the now defunct roughly half-mile long curved section between Hop Brook and Nobscot Road, the “Road to Framingham” on Wood’s map and the “County Road from Framingham” on Mosman’s map, part of which I have shown in green on the map below. The original road likely passed along Maple Avenue, then the road would have curved west across the property of #15 Maple Avenue and straddled the property line of 236 Raymond Street and Feeley Park.

Another clue to the original route of the Boston Post Road can be found on Wood’s 1830 map, which shows a the house of a “W. Rogers” at a junction where today’s Raymond Road turned south sharply and the old post road began to curve back up towards the contemporary road. A house listed on the Sudbury Historic Inventory as the Walter Rogers house at 225 Raymond Road still exists at exactly the spot marked on the map. After passing the Rogers house on Raymond Road the old road continued into what is today a wooded area and followed the curve of the property line along the rear of the Sudbury Crossing shopping center until it reached Nobscot Road, the old “Framingham Road”. Finally the old road continued across Nobscot and through the property of Fairbanks Septic Pumping, before reconnecting with the road that still exists near Sullivans Tires along Route 20 at 475 Boston Post Road.

A glance at a map from 1943 of the topography of the area prepared by the U.S. Geological Survey (USGS) hints at why the road might have curved in such a manner; the ground along the path of the curved road is significantly higher than the low-lying and marshy area just to the north. One can only assume that road-building skills had improved significantly by the early-nineteenth century in order to allow so many straight roads to be built through risky flood-prone areas in the period between the maps of Mosman (1795) and Wood (1830).

Continuing along the contemporary straight road through the marshy areas I reach Union Avenue and the very busy Sudbury Crossing shopping center. The walk at this point along Boston Post Road is principally past gas stations, banks and restaurants. Sudbury Plaza, another shopping center, appears just past Nobscot Road where the curved part of the original road would have rejoined the main road. A small section of low-lying marshy area adjacent to the road is a reminder of the tricky topography through which the road threads in Sudbury, as well as a small bit of visual relief from the commercial sprawl. Almost immediately beyond the reeds I encounter Meadow Walk the largest development of them all, 75,000 ft2 of retail space, the centerpiece of which is a Whole Foods Grocery store, as well as three separate residential complexes with, according to the website, “generous public areas including a central green and pond surrounded by walking paths and meadow-like open spaces.” I think the addition of the suffix “-like” to the word “meadow” says it all, while a glance at the aforementioned USGS map from 1943 illustrates how much has changed in the intervening years along this stretch of Boston Post Road.

That there is a branch of the expensive grocery store chain here is unsurprising as Sudbury, like the preceding towns of Weston and Wayland along the route of the Upper Boston Post Road, is among the wealthiest towns in Massachusetts. Sudbury, at $218,000, has the fifth-highest median household income(HHI) in Massachusetts, a state with the second highest median HHI ($67,000) behind only Connecticut. The town of 18,934 residents, according to data from the 2020 US Census, is about 80% White, with an increasingly large population of Asian descent, over 9% according to the Census. Black and Hispanic residents together comprise only about 5% of the total, much like the preceding towns in the wealthy Metrowest Area of Boston. Like its neighbors along the Upper Boston Post Road, the population of the town of Sudbury has increased dramatically since World War II: From 1754 inhabitants in 1940 the population by 1950 had grown to 2,596 residents, and by 1970 the population had increased to 13,506 inhabitants; the number continues to climb albeit more slowly. The development along the road is merely a reflection of the increased demand for goods and services of a mostly wealthy population seven times larger than it was in 1950.

Once past the Whole Foods, the nature of the commercial/residential development along the road, if not perhaps diminishing much, at least modulates slightly. At 554-560 Boston Post Road is “Ye Old Farm Stand”, which is exactly what it purports to be although, as the farm stand fronts an area with a number of large greenhouses, all part of J.P. Bartlett Wholesale Greenhouses, a business that has been here since 1911, the “Ye” is probably a bit ambitious. A building adjacent to the farm stand has a sign indicating it is the Stone Tavern from 1804, about which Hudson says “A tavern was kept for a while at the Stone place, about a mile west of Mill Village. Mr. William Stone was its only proprietor, and it years ago ceased to be used as a public house.”35Hudson, p. 590. Maybe if they put the farm stand in the Stone Tavern building the “ye” might have a little more justification!

Hagar House 1730 at 850 Boston Post Road. Could the gravelled area in front of the house be the original route of the Boston Post Road?

From the “ancient” farm stand the road to the Wayside Inn hugs the north side of a substantial set of hills to the south, with names like Tippling Rock and Nobscot Hill, the highest hill at 602 feet above sea level. At Dudley Road I encounter another of the faux “milestones”, this one purporting to be the “27-mile” stone according to the Sudbury Historical Inventory. There are six “milestones” in total listed on the inventory, spanning just under four (3.7) miles from Landham Road (the “24-mile”stone) to Dutton Road (the “29-mile”stone) just beyond the Wayside Inn at the Martha-Mary Chapel. A simple mathematical calculation: 29-24=5 demonstrates that something is not right here. Again, it is my contention that these stones, rather than being milestones from the eighteenth century, were instead modern stones carved roughly to appear to be old and placed at major road junctions along Boston Post Road sometime in the 1920s for aesthetic reasons. Ye Olde Milestones, to borrow a phrase.

Junction of Wayside Inn Road and Boston Post Road. Note the granite stone inscribed with the the words Wayside Inn, looking remarkably similar to the “milestones” along the route of Boston Post Road

The stones are at least more interesting than most of the other stuff along the road in this area, with one little shopping plaza following another, along with some ugly housing and little of interest. Just beyond the Fairfield Inn a sign indicates the start of the Wayside Inn Historic District. There is evidence along this stretch of road that perhaps it has been slightly altered in the last century as maps from 1908 and earlier show the road in this area with sharper curves while the road today is relatively smooth with no tight curves. The first few hundred yards of Lafayette Drive, a newer road, runs roughly parallel and very close to Boston Post Road before turning sharply to the north. More evidence is found in the curious placement of the utility poles which for long stretches run 30-40 yards away from the road in the woods before occasionally rejoining the road. It is possible these little anomalies are phantom traces of the route of the original road.

Just before Peakham Road we pass into what was once the eastern boundary of the 2823 acre property owned by Henry Ford. At 850 Boston Post Road is the first example of Ford’s machinations, the William Hager house of 1730. This was at one point situated over the line in Marlborough but was moved to this location near the entrance to Wayside Inn Road and became the Nobscot Teahouse.36Plumb, p. 124. The house is set back a few yards from today’s road and there is again a palimpsest of an old road in the gravelly areas under the power lines that are oddly distant from the main road (see the photograph of the Hager house above for example) .

Shortly thereafter I encounter another of the stone markers placed by the Wayside Inn Chapter of the DAR. This marker indicates the site of another of the fortified houses of the seventeenth century, this one known as the Parmenter Garrison house. The area later became the Parmenter Dairy farm as part of Ford’s ambitious plans for a working colonial-era village. The stone is set back at least twenty yards from the road and through the adjacent shrubs I can make out what appear to be traces of the older road along which I have a direct line of sight to the Hager house a few yards away. It seems very likely that US Route 20/ Boston Post Road was straightened and shifted slightly in the Wayside Inn Historic district and that the path of the old road is in the woods a few yards north of the contemporary road beneath the bushes and trees that have grown up since the original road was abandoned. Finally, five-miles distance from the previous DAR marker at the Old Town Bridge in Wayland where I began this walk, I reach the junction of Boston Post Road and Wayside Inn Road; I bear right onto the latter, escaping the traffic of Route 20 and make my way back to the Wayside Inn.


Chapter Nine. The Traveler’s Tale. Bar Stories.

February 25, 2021. The Old Bar Room at The Wayside Inn, Sudbury, Massachusetts.

The Bar Room, Wayside Inn, Sudbury. A video showing the room as it is in 2023.

Marvin, the bartender in the Bar Room for the best part of twenty years, mixes up a Coow Woow which the little card on the table claims is “the very first mixed drink in this country dating back to the early days of 1664,” a claim I leave to more experienced tipplers to dispute.37Brian Plumb states (p. 134) that it was introduced by Frank Koppeis, innkeeper from 1959-1989. Standing behind the railed bar, the gregarious Marvin regales me with lore about the artifacts in this most atmospheric of all rooms at the Wayside Inn (see my video above). It is easy to picture “around the fireside at their ease” Longfellow’s “group of friends, entranced with the delicious melodies.”

As you might expect, given the nature of this entry, the history of the Bar Room and indeed of Longfellow’s connection to the Wayside Inn is complicated. The seven tellers of tales were placed by Longfellow in the nearby parlor rather than in this room. Although the Bar Room is an ancient room, likely one of the original two rooms of the house built by David How in 1702, it’s history as a bar is uncertain.38See Plumb, pp. 27-28. Sudbury was a “dry” town for decades so alcoholic drinks were not even served at the Wayside Inn in its modern incarnation (essentially from 1897) until the struggling inn applied for a liquor license in 1953. A fire did significant damage in 1955 to much of the building, including the Bar Room, and it was subsequently restored to the late colonial era of Longfellow’s poem.39Plumb, pp. 131-132. Even then, this room was not the bar until 1992, and was instead “used for people waiting for dinner. There was no service. The room contained several museum objects that could not be touched. In 1992, Bob Purrington, the next innkeeper from 1989 to 2009, turned the Bar Room into an actual working bar, making it once again the heart of the inn.”40Plumb, pp. 145-146.

The Wayside Inn became famous as a result of the immense popularity of Longfellow’s book of poems, Tales of A Wayside Inn, published in November 1863. While the poems may not be read much today (although most people are at least familiar with the first lines of the Landlord’s Tale: “Listen, my children, and you shall hear, of the midnight ride of Paul Revere”), the book was very popular when it was published.41Longfellow is widely acknowledged to have been the most popular poet in America in the nineteenth century. He was also very popular in Europe and is still the only American poet with a bust in Poet’s Corner in Westminster Abbey. Longfellow himself apparently visited the inn only once, in October 1862, while working on the poems that would become Tales of a Wayside Inn, only to discover, according to his journal entry “alas, no longer an inn!”42Plumb, p. 77. He was shown around by one of the residents at the time and used the details gleaned from the tour to create his description of the inn. Like all good stories, there was a mixture of fact and fiction; the characters portrayed were all based upon real people, almost all acquaintances of Longfellow, but the circumstances of their visit was complete fiction, a variation on the setting and structure of Bocaccio’s Decameron.

The popularity of the poems brought visitors to the putative site of the semi-fictional setting which, as mentioned above, had ceased to be an inn by 1861, when Lyman Howe, the last of the generations of Howe family “landlords,” died without issue. Eventually the inn was purchased by a Longfellow fan and wealthy businessman, Edward R. Lemon, who rechristened the former Howe Tavern the Wayside Inn in 1897.43Plumb, pp. 84-6.Henry Ford purchased the property from Lemon’s widow in 1923, and expanded the property as described in previous sections. In 1944 the Wayside Inn Trust was created to control, operate, and preserve the inn, which they continue to do to this day as the Wayside Inn Foundation.

The Wayside Inn is, in many ways, a recreation of a fictional tavern from a book of nineteenth-century poems. It. has suffered devastating fires, it ceased to be an inn for decades and it has been chopped and changed dramatically over the centuries. However, there is still to be heard, underneath all the noise, the still-beating heart of the original humble tavern along the Post Road, serving the traveler passing through on their way to nearby Marlborough or to New York and points beyond. Nostalgia, reconstruction, and renovation aside, this building has been here on the Upper Boston Post Road for over three centuries. As Hudson says in His History of Sudbury “stripped of every feature of romance which may properly have been given it by the great poet’s pen, the Wayside Inn is a grand old landmark…that some of the traditions are true is probable, that some are not true is also probable…it needs no embellishment of fancy to give to it a sufficient charm or make it rich in rare reminiscences.”44Hudson, pp.591-597. Part of what makes the Wayside Inn interesting is the very contorted history of the place. Brian Plumb, in his detailed History of Longfellow’s Wayside Inn,45Better yet, get it directly from the gift shop at the Wayside Inn provides a treasure trove of information about the people who have been associated with the inn and about the history, the legends, and the changes that have taken place at the inn over its three-centuries of existence, in much more detail than I can relate here. My small contribution to the story is to describe the Upper Boston Post Road as it passes through the property of the Wayside Inn.


Chapter Ten. A Forty Year Walk.

October 16, 2023. Junction of Boston Post Road (Route 20) and Wayside Inn Road.

0.3 miles from the Wayside Inn.

Whatever else Henry Ford may have done, I am grateful for his deep-pocketed efforts to have the course of US Route 20 shifted to the south of the original Boston Post Road in the area surrounding the Wayside Inn, which effectively preserved a 1.5 mile section of the original road, freeing it from the roaring traffic and development that has dampened my spirits and blighted large sections of my walk across Sudbury. As I mentioned earlier, today’s Boston Post Road (Route 20) and the original route of the Upper Boston Post Road are roughly the same with three major exceptions in the town of Sudbury. The first is Old County Road from the Training Field on the border with Wayland to the junction with Route 20 at the Herb Chambers showroom. The second is the short curved King Philip Road just before reaching the center of South Sudbury. The mile and a half of Wayside Inn Road (half a mile of which is technically in Marlborough) comprises the longest and one of the most well-known segments along the entire Upper Boston Post Road. 46In total, the amount of the original route of the Upper Boston Post Road that follows today’s Boston Post Road in Sudbury is about 2.9 miles of 5.1 miles, a little under 60% of the total. If, as I suspect, significant portions of the road were also straightened, for example the Lafayette Drive section, then the total likely falls under 50%.

After leaving the busy main road behind I walk along a peaceful road lined with classic New England stone walls and catch an occasional glimpse of a field through the woods. In a quarter-mile I reach the gravel drive of the Wayside Inn and, to the left, the meadows from my memories of forty years ago. Apparently Ford was not the only owner of the Wayside who managed to get the main road moved away from the Wayside Inn. In 1899 Edward Lemon also managed to convince the town to shift the road about twenty yards south of the inn, which technically means that the driveway of the Wayside Inn is actually the original route of the Upper Boston Post Road.47Plumb, p. 89. So, for another quarter of a mile, I walk along a graveled path that feels much as it might have three centuries ago. Once again I am confronted with the issue of authenticity as the path itself is probably a twentieth-century reconstruction of an eighteenth-century path, but the road itself underneath any modern attempts to make it look old is as real as it gets.

Entrance drive to Wayside Inn. In 1899 Owner E.R. Lemon had Wayside Inn Road moved twenty yards south (visible at left) so this gravel drive is likely the original route of the Upper Boston Post Road.

Along the right hand side of the drive is a low brick wall; halfway along is a plaque with an effigy of Longfellow, placed there by Lemon, flanked by four lines from Tales of a Wayside Inn:

Round this old-fashioned, quaint abode
Deep silence reigned...

And through the ancient oaks o’erhead
Mysterious voices moaned and fled.

It is easy to be swept away. Yes the bucolic landscape has been sculpted, yes the entire place exudes romance, and yes I also have romantic and deeply personal connections to this place, but the road is not some romantic legend, it really existed and this section of the road, regardless of the machinations of Henry Ford and the sentimental associations with a nostalgic past, is very real. George Washington really did pass this way, as did many travelers in the colonial era. The marker commemorating Washington’s passage on this road is just ahead along with another marker commemorating the passage of the Marquis De Lafayette, either of whom may or may not have stopped here.48No evidence exists supporting any claims that either Washington or Lafayette ever slept or even stopped at the inn. Nevertheless, as the road passes the inn and both men traveled the road on a number of occasions, they certainly at least passed the inn on their travels. See Plumb, p. 37. Finally, the oak-lined drive leads to the majestic inn with its famous sign of the red horse. I have been here before.

Washington did not sleep here but he did pass this way.

Few travelers in the colonial era record stopping at How’s tavern in Sudbury; most of the diaries and journals I have consulted typically record a stop for lunch or baiting horses in Weston on the way out from Boston and then an overnight stop in Marlborough. Samuel Sewall mentions in his diary entry for Monday August 27, 1716 that he “got to How’s about 1/2 hour by Sun” on the way to Springfield, which the editors note is “the famous Wayside Inn in Sudbury.”49Diary of Samuel Sewall, Volume III, p. 100. I remain unconvinced, however, as there was a more established How’s tavern about five miles further along the road in Marlborough, established in 1661 by David How’s grandfather. It makes more sense for him to have stopped in Marlborough, given that his next stopping point was “dining in Worcester,” meaning he stopped in Worcester for lunch the next day. Wilson’s, his stop previous to How’s, was located in Weston at “mile 16”, meaning he would have traveled only about ten miles further before stopping for the night at the Wayside Inn, which seems unlikely if he then covered the subsequent twenty miles or so in the course of a morning. It is more likely that Sewall followed an intinerary similar to the one recorded in his diary eighteen years earlier when, on August 15, 1698, he traveled to Springfield from Boston; the first night he “lodg(ed) at Marlborow,” while on the return trip on August 26 he also stopped at Marlborow before returning home on August 27. 50Diary of Samuel Sewall, Volume I, pp. 482-484.

A traveler’s booklet called Vade Mecum, published in Boston in 1732, lists taverns along the road from “Boston westward thro’ Worcester to Springfield on the Connecticut River.” Wilson’s in Weston is sixteen miles distant from Boston, while Balding’s (likely Baldwin’s in Wayland, discussed in the entry on Wayland), is the next tavern listed four miles further along the road and twenty miles distant from Boston. The next entry, ten miles further on from Baldwin’s and thirty miles from Boston, is “How’s” in Marlborough. From How’s it is fourteen miles distance to Jennison’s in Worcester, forty-four miles from Boston. This seems the more likely How’s tavern at which Sewall recorded stopping in 1716.

The diary of John Adams is similarly devoid of references to How’s Tavern, although Adams did stop at a Munn’s tavern in Sudbury in 1771, a tavern about which I have been unable to discover anything more. Typical are entries like the one on November 12, 1798 when he writes to “His Dearest Friend” Abigail from Flagg’s tavern in Weston and expresses his “hope to reach Williams’s at Marlborough, and Sleep there this night.” Washington records passing through Sudbury on October 15, 1789 but makes no mention of stopping at the Wayside Inn, stating that he dined at Marlborough and lodged at Weston on his way to Boston. Similarly the spies Browne and DeBerniere start their harrowing adventure on March 1, 1775 from the Golden Ball Tavern in Weston, travel to Marlborough and return in a snow storm through Sudbury the same day without mentioning How’s Tavern. With the exception of Henry David Thoreau’s journal entry of May 21, 1853 when he “Left our horse at the Howe tavern. The oldest date on the sign is “D. H. 1716.” An old woman, who had been a servant in the family and said she was ninety-one, said this was the first house built on the spot,” there are few mentions of the Wayside Inn/ How’s Tavern/ Red Horse Inn that predate Longfellow’s poem.

How’s isolated inn, “Remote among the wooded hills,” might have been a bit too remote for many of the long-distance travelers along the Upper Boston Post Road; it appears to have been bypassed much like the express train from Boston to New York skips over most of the local stations. The one record I have found of a visit to the Wayside Inn in the colonial period was the diary entry of a young Ebeneezer Parkman who, in traveling back to Cambridge from Worcester on August 14, 1723, turned down an offer of accommodation in Marlborough for fear of being late for a lecture the following morning in Cambridge,51He missed the lecture anyway so “continued on to Sudbury. It was too late to gain the Town (meaning contemporary Wayland). We stop’d at David How’s Tavern, and having Eaten part of a Fryed Gosling for supper, prayed, etc., we repair’d to repose.  N.B. This was the first Time that I ever Lodged in a Tavern on the Road.” Parkman would go on to become minister of the nearby town of Westborough and his more than sixty years of diary entries are a rich source of information on the roads and taverns of the area. The fact that Parkman clearly stopped at How’s only because they couldn’t make the next town before dark lends support to my hypothesis that the tavern likely served a mostly local clientele or travelers “stuck” between towns. Parkman records stopping at “Mr. David How’s” at least six more times in his diary between 1723 and 1744; on no occasion does he stay the night again, although he does take a nap before dinner on August 14, 1742.

Perhaps unsurprisingly there was a dramatic increase in records and reminiscences of the inn after the publication of Longfellow’s book. Many accounts are similar to that of Lydia Maria Child who, in 1872, fondly recalled in extravagant detail a visit to the inn in 1828, forty-four years and one very famous poem after the fact.52Plumb, pp. 45-46. I hesitate to trust these romantic accounts of the halcyon days of youth, seen as they are through the gauzy prisms of both Longfellow and of time, much as I would hesitate to trust my version of my own visit to this place forty-two years ago.

The documented historical record of the Wayside Inn is fortunately more clear on maps of Sudbury produced over the years. Mossman’s 1795 map of Sudbury is light on detail so perhaps it is unsurprising that How’s Tavern is not shown, although “Joseph Howe’s gristmill” is shown on the map along the “Post Road from Worcester to Boston.” On William Wood’s map, produced thirty-five years later in 1830, “Adam Howe’s Hotel” is prominently marked, as is his relative Buckley Howe’s Grist mill (see Wood map above). Similarly both the grist mill and the “Hotel” of Lyman Howe are shown on Walling’s map of Middlesex County in 1856. A map of Sudbury from the Middlesex County Atlas of Frederick Beers published in 1875 calls the property “Wayside Inn,” the first map I have found showing the Inn with its modern name. The 1908 map of Middlesex County shows the property as “The Wayside Inn” of “E.R. Lemon,” the name he had officially given to the Inn when he reopened it in 1897.

Like Washington and Lafayette, Sewall and Adams, Browne and DeBerniere, I continue my journey along the Post Road after passing the Howe Tavern/ Red Horse Inn/ Wayside Inn.53Thoreau, typically, was going for a walk up Nobscot Hill rather than traveling along something so pedestrian as the Post Road For a few hundred yards I continue on the gravel path which is likely the original route of the road. The path ends at the junction of Wayside Inn Road and Dutton Road, where another of the granite milestones sits. My earlier hostility to these artificial milestones has abated as I come to the realization that, like the Wayside Inn itself, the ambitious efforts of Ford and others a century ago to recreate a colonial atmosphere along the Post Road are at this point also historical artifacts of the road. The stones are not original like the one near my house in Jamaica Plain but they are authentic in their own way. Part of my goal is to make the distinction without necessarily condemning the more modern efforts; however I still reserve the right to criticize the all too frequent wanton destruction of natural and historical resources. The stones, the developments, and the Wayside Inn are all a part of the history of the Upper Boston Post Road.

On the hill behind the stone marker is the similarly new/old Martha-Mary Chapel, now almost a century old itself and a memorial to a different era, as well as a place of special personal significance. A few yards further, on the left-hand side of Wayside Inn Road the Grist Mill comes into view, followed by the Grist Mill Pond, after which the road enters a wooded area. There are only one or two modern houses along this last 0.3 miles of the Upper Boston Post Road in Sudbury, but the recent appearance of an ominous clearing in the woods does not bode well for the future of this area. After 0.7 miles walk from the door of the Wayside Inn, I reach the junction with Sudbury Street and cross the border into Marlborough. A few hundred more yards along Wayside Inn Road in Marlborough brings me back to Boston Post Road where the noisy traffic I had evaded for so long returns with a vengeance.

I wonder whether the bucolic stroll of only a few minutes before was all just a dream as I march along with the traffic along Route 20 through the morass of big-box stores, self-storage facilities, and gas stations that blights large sections of the road in this area…

….but, since this is my story, let’s stop before then, and stay on the quiet gravel path of the Old Post Road. Even if it is a reconstruction, it is certainly more pleasant than this part of the road or even the “meadow-like open spaces” (of which I found very little) of Meadow Walk with its Whole Foods and thousands of square feet of retail and residential development and parking lots. My story along the Upper Boston Post Road will continue into Marlborough and beyond another day, but for now I will linger alone with my memories here in the meadows by the Wayside Inn.

A region of repose it seems,
A place of slumber and of dreams,
Remote among the wooded hills!
For there no noisy railway speeds,
Its torch-race scattering smoke and gleeds;

Henry Wadsworth Longfellow, Tales of a Wayside Inn, 1863.


Sign of the times?

The End


This entry is dedicated to Mary and Ernest Comi, who generously welcomed me into their lives and with whom we shared many special moments at the Wayside Inn.

Distance traveled in this entry: 5.1 miles from the Training Field to the Sudbury/Marlborough line at Wayside Inn Road and Sudbury Street.

Total Distance traveled along the original route of the road from the Old State House in Boston for this project: 26.7 miles.

Total Distance covered for all the walks described in Boston Rambles: 86.3 miles

2 Responses to Sudbury, Massachusetts: Once Upon a Time…

  1. […] in 1923 with an eye toward creating a historically-themed village, a topic I discussed in the previous entry. Ford ultimately acquired nearly 3000 acres of property surrounding the Wayside Inn, extending more […]


Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes:
<a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>