Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Wayland, Massachusetts: Waylaid in Wayland

Upper Boston Post Road #5 (UBPR #5)

The remnants of the last “Old Town Bridge” over the Sudbury River in Wayland. The first of the many bridges at this location was built in the early 1640s, the last in 1848, a four-arch stone bridge built by William Russell, with modifications in 1903. The maps below show that this bridge crosses over to what is essentially an island, as there is a channel of the river on the far side which also required a bridge crossing. The Sudbury River flooded in 1955, destroying the causeway on the west bank as well as the second, or “Canal” bridge. Instead of repairing the old bridge, the road was rerouted slightly to the south with a new bridge.1see page 19 of Wayland Historical Tours

“We were resolved to go the Sudbury road, (which was the main road that led to Worcester ) and go as far as the the thirty-seven mile-stone, where we had left the main road and taken the Framingham road.”

Ensign Henry DeBerniere, from his report to General Thomas Gage, describing the activities undertaken with fellow spy Captain William Browne as they attempted to survey the countryside around Boston in the winter of 1775.


I have a problem, and it’s not just that all I can think about is Monty Hall as I cross the border from Weston into Wayland. Call it the “Three Roads Problem.” Immediately upon entering Wayland I reach an important junction and I am confronted with a dilemma. Boston Post Road continues directly ahead along US Route 20 in Wayland for another 1.5 miles; this is the logical route and was certainly the principal route of the road to Worcester and Springfield by the early 1720s. This was the road traveled by George Washington on his trips to Boston in 1776 and 1789. This is the road labeled Post Road from Springfield to Boston on the official surveyor’s map of Wayland produced for the state of Massachusetts by Matthias Mosman in 1795 (shown below). This is the “Sudbury road…the main road that led to Worcester” in the words of the spies sent out to survey the countryside around Boston in 1775. 2General Gage’s Instructions of 22nd February 1775, p. 10.

However, two more roads branch north and south from here, both with claims to the title of the earliest path west. The first, today’s Plain Road in Wayland, is considered by historians of the town, as far back as A.S. Hudson’s History of Sudbury, Wayland, and Maynard (1891), through to Wayland Historical Tours (1976; revised and updated 2013) to be the original trail followed by the English settlers of the town of Sudbury in the late 1630s.3Alfred Sereno Hudson, The Annals of Sudbury, Wayland, and Maynard, Middlesex County Massachusetts (Sudbury, Massachusetts. Published by the town, 1891), pp. 37-38. According to speculative maps of early Sudbury drawn in the 1880s by a local amateur historian and town notable, James S. Draper, and included in Hudson’s book, what is today the main road did not exist until the early eighteenth century. Perhaps Plain Road is the earliest road west and therefore I should follow that road.

The Three Road Problem. Detail from the 1819 Map of Boston and its Vicinity by John G. Hales. This section of the map shows most of what was then called “East Sudbury” but which is today known as the town of Wayland. In the right center of the map (to the right of the “Dr Heyward” house) at the border with Weston (the pink is Weston), three roads diverge. The northernmost road is today’s Plain Road, the middle road is Boston Post Road (Route 20), and the southernmost road is the so-called “Old Connecticut Path.” All three roads have claims to being the “first” or “principal” road in Wayland as the article below explains.

A second road presents an even bigger conundrum as it was the road followed initially by the spies Browne and DeBerniere in February 1775 on their way to Worcester and a few months later by John Adams on his way to Philadelphia. This is the so-called Old Connecticut Path, which leads to Framingham and the tavern mentioned in the narrative of DeBerniere as well as in the diary of John Adams kept by Colonel Joseph Buckminster. It may even have been the road used by Colonel Henry Knox in the winter of 1776 when he was charged with bringing the train of artillery captured at Fort Ticonderoga to Boston for use against the besieged forces of the King’s Army. The Old Connecticut Path has been described as the path taken by the first migrants to Connecticut in the early 1630s4Hudson, p.37, and so also has a claim to being the original road west.

Which brings me to Monty Hall, who was the co-creator and original host of the television game show Let’s Make a Deal, which first aired in 1963 and has been on the air virtually ever since. Contestants “make deals” with Monty and accrue prizes of some value. The grand finale of the show is the “Big Deal”: behind one of three doors is a fantastic prize while behind the other two doors are lesser prizes (goats were a favorite choice), called “zonks” in Let’s Make a Deal parlance. The contestants with the most accrued assets during the show are asked if they would like to trade what they have accumulated for what is behind a door of their choosing. If they opt to play and choose a door, let’s say door number one, they will then be offered a second choice: Stick with door number one or pick either door number two or three instead. To make things even more tempting, Monty would then open one of the two remaining doors, let’s say door number 3 in this example, to show that behind that particular door is a zonk, thus making the choice between door number one and door number two, one of which definitely has a nice prize behind it.

Although this was never quite the way it actually happened on the show (trust me, I watched a bunch of them to check), this particular scenario is the basis of a famous mathematical problem which has come to be known as the Monty Hall Problem (or sometimes the Three Door Problem), in honor of the eponymous host. Essentially the problem states that a contestant picks one of three doors, only one of which has a big prize. The host, knowing where the prize is located, now opens one of the two remaining doors, behind which is a zonk. The offer to switch to the remaining unopened door is then made by the host. Should the contestant switch?

The intuitive answer would be not to switch doors because the odds were 1 in 3 to start with and are 1 in 2 now that you know door number 3 has a zonk. In fact, based on the assumption that the host knows what is behind the doors, always opens one of the two remaining doors, and has deliberately shown you a zonk, the chances of the prize being behind door number 2 are now 2 in 3 and the contestant should in fact switch to door number 2. If this sounds wrong, trust me, you’re not the first person to think that. Marilyn vos Savant gave this answer when she was asked this question in 1990 in her Parade Magazine column and was pilloried in literally thousands of letters, hundreds of which were written by math professors and other experts, many of which were quite vitriolic in their criticism of her math skills. However, she was ultimately proven correct. This article in Wikipedia does a good job of explaining what the problem and the fuss is all about. The main point is that the problem is not as obvious as it seems and its seeming simplicity is actually deceptive. Here, for example, is an article from Scientific American, that goes more deeply into the math.


I have a Three Road Problem, a variation of the the Three Door Problem. Do I charge forward along Boston Post Road, damn the torpedoes, full steam ahead, and ignore the urge to deviate from the straight path? After all, this project is about following the Upper Boston Post Road, and the road is clearly in front of me. On the other hand, my principal interest in the essays is in finding and following the oldest roads and the information in histories of Wayland suggests that Plain Road is the earliest road that was used by English settlers and even by the people who lived here long before the arrival of European immigrants. Then there is the fact that the diaries I have been assiduously scouring for information about the “right” road explicitly do not follow the main or post road at this juncture. Browne and DeBerniere, John Adams, Henry Knox; none of them seemed to have followed the main road in Wayland. If I choose one road, what if the other road had a bigger prize? What if the Boston Post Road was not the main road west after all? Is this project even worth pursuing anymore?

Fortunately, I do not have to make an irreversible decision. I can follow the sage advice of the inimitable Yogi Berra: When you come to a fork in the road, take it! Realistically I do not want to walk all three roads as this will make the project impossibly complex and I will never get past Wayland. However, I can investigate the other roads and use that information to inform my research on the main subject of this project, the Boston Post Road. For instance, reviewing another of Draper’s historical maps, this time of Wayland at the time of the American Revolution, it quickly becomes apparent that whatever paths the settlers might initially have used, the original paths were quickly superseded by the 1720s, when the “main” road from Weston to Wayland was definitively established. In some ways, Plain Road is a “zonk” in that it never was a principal road of travel through what was known as Sudbury in the Colonial era. It was, and remains, primarily a local road in Wayland. A glance at the map above of Wayland in 1819 (the town was called East Sudbury from 1780 until 1835), shows that the road heading northwest from the three-way junction at the border with Weston meanders with no clear destination. A traveler would likely get lost trying to make their way along the various twists and turns required to get to the bridge over the Sudbury River; even this author had to constantly look at the map to figure out which turn to make as he followed the road(s) along this putative “old route”.

A glimpse at what was behind door number two: Reeves Tavern on Old Connecticut Path in Wayland, dating to 1762, visited by John Adams in 1774.

This leaves me with a choice between road number one, the Boston Post Road, or road number two, The Old Connecticut Path. Whether this putative “original road to Connecticut” was indeed the original road, a topic about which I am deeply skeptical as I will explain in a future entry, it is undoubtedly true that John Adams followed this road numerous times in the 1770s on his way to Worcester, as did the spies Browne and DeBerniere. It can be argued however, that Adams had a particular reason to travel this way, namely that he wanted to visit Colonel Buckminster in Framingham.

Why Isaac Jones, proprietor of the Golden Ball Tavern in Weston, recommended this route to the military spies is more of a mystery. However, even the spies acknowledged in their report that the main road was the road directly ahead, what they called the Sudbury road, what is now called Boston Post Road at this spot in Wayland. Browne and DeBerniere did in fact eventually follow the main road after traveling to and from Worcester via the alternate Framingham road.

Finally, there is the question of Colonel Knox and his decision to deviate south from the Post Road in Marlborough. There are plaques commemorating the Knox trail along the Boston Post Road in Worcester, Shrewsbury, Northborough, and Marlborough, so it is thought he followed the main road on his journey east from Fort Ticonderoga in New York at least to Marlborough, the town immediately to the west of Sudbury, before his men deviated south from the main road and passed into Southborough then continued east to Framingham. We also know that Knox passed through Weston, Waltham, and Watertown on the final stages of the journey to Cambridge. Since he stopped keeping his diary after January 11, 1776 (in Westfield, Massachusetts) it is unclear exactly what happened between Marlborough and Wayland or why a decision was made to take a detour to Framingham. However, John Adams reports on the artillery in his diary entry of January 25, 1776 while visiting Buckminster in Framingham, and it seems clear that the artillery was taken deliberately to be stored in Framingham before being shipped to the environs of Boston. Thus it seems there was a plan for the artillery and that the deviation from the main road had nothing to do with the Post Road as a suitable road of transport.

In the end, I am “resolved to go the Sudbury road”, to follow road number one, the Upper Boston Post Road. Es muss sein! However, having been “waylaid” in Wayland as it were by this conundrum, I have accumulated a great deal of information on the so-called “Framingham Road”. While the present entry will follow the route of the Post Road across Wayland into Sudbury, a separate entry is also being prepared about the alternative route taken, what I refer to as the “Framingham Diversion”, which will appear in the near future. That article will trace the route of the path taken by Adams, and by Browne and DeBerniere, a distance of twenty one miles, through Wayland, Framingham, Southborough, and Westborough, before the divergent path rejoins the Post Road in Northborough, and continues on through Shrewsbury to Worcester.


In the meantime, damn the torpedoes! The border between Weston and Wayland marks an invisible transition in the walk along the Upper Post Road. The first four entries in this project, across Watertown, Waltham, and Weston to this spot along the Post Road, 8.3 miles distant from Watertown Bridge, all passed through territory originally belonging to Watertown. The walk from here through Wayland, Sudbury, and Marlborough will pass through territory originally part of Sudbury, the third settlement by Europeans in inland Massachusetts, after Dedham and Concord, in 1638.5Helen Fitch Emery, The Puritan Village Evolves: A History of Wayland, Massachusetts. Canaan, NH: Phoenix Publishing, 1981. p.3. Sudbury was divided into two towns in 1780, and East Sudbury eventually became the town of Wayland in 1835. Confusingly the original settlement of Sudbury was located in what is today the town of Wayland, for reasons which will be explained later.

An auspicious start in Wayland

At the moment however, it is time to move along in Wayland after being waylaid by the three roads problem for far too long. The initial prospect is promising, with the Coach Grill sitting at the junction of Old Connecticut Path and Boston Post Road. An inn located at “Wayland and Weston Corner” was located on the site of the Coach Grill as early as 1765, kept by Nathaniel Reeves, whose father kept another tavern in a building that still exists, a little further along the Old Connecticut Path (see the photograph above).6Hudson, p. 134

Almost immediately I pass Post Road Fine Wine & Liquors across the street from the Coach Grill, so at the very least, if my gamble is a failure I know where to seek succor. Strangely, the next mile proves to be disappointing; I fail to find any markers or buildings that are the breadcrumbs I usually use to navigate my way along an uncertain path. The first eighteenth century building I encounter is at 202 Boston Post Road, a building dating to the Colonial era built by Jonas Noyes, 1.3 miles along Boston Post Road from the Weston border. However, it is currently being renovated and is so undistinguished that, had I not found the house in the Wayland Historical Tours booklet (p. 34), I would have passed it without a second glance.

As no other buildings in the guide are listed along the road I have just traveled, I assume there are no more “hidden gems” to be discovered along the busy first mile of my walk in Wayland along Boston Post Road. Alfred Sereno Hudson, in his Annals of Sudbury, Wayland, and Hudson (1891), lists all the buildings along the road from “Bigelow’s Corner” (the area around the Coach Grill) to Wayland Center extant at the time, according to the research of his companion James S. Draper, with the caveat that “they are given not as absolutely correct in all cases, but as the best approximate estimate at the time of the writing.”7Hudson, pp. 114-115. Incidentally the “Corner Tavern” is listed as an extant building in 1891.8It was apparently consumed by fire in 1902 or 1903. See Evelyn Wolfson and Dick Hoyt, Wayland A-Z: A Dictionary of Then and Now. (Saline, MI: McNaughton & Gunn, Inc, 2004), p. 223. From there, along Boston Post Road, 25 further buildings are listed up to and including the Unitarian Church, built in 1814 and still standing at the junction of Boston Post Road and Cochituate Road in the center of Wayland. With the exception of the house of Jonas Noyes, who died in 1775, and the locations of two cellar holes belonging to demolished houses, no house existed along Boston Post Road in 1891 dating to the period when Matthias Mosman compiled his map of Wayland for the state of Massachusetts in 1795 (see below).

The absence of Colonial-era evidence along the first stretch of road in Wayland is disconcerting, particularly as there is an extant tavern building along Old Connecticut Path at which John Adams stopped in 1774. 9Diary of John Adams, Volume II, p. 160. “1774. Wednesday. Novr. 8. Break fasted at Reeve’s of Sudbury.” Another factor that I begin to contemplate as I pass a small pond just beyond the Noyes house is that the road around the junction with Cochituate Road seems peculiarly low-lying, not unheard of, but generally uncharacteristic of Post Roads I have followed thus far. The Wayland Historical Tour booklet (p. 13) points out the absence of an east west road in Wayland Center in the seventeenth century and suggests that “the two original trails of the settlement that followed higher ground—the upper route (Watertown Trail, Plain Road) or the lower route (Old Connecticut Path)—remained the main highways to the interior or coastal areas during this time.” Again doubts creep in about whether I have chosen the wrong road to follow.

Plaque commemorating President George Washington’s journey along this road in 1776, situated in front of the First Parish Church in Wayland (1814) at the intersection of Boston Post Road and Cochituate Road (Route 27).

My luck turns in front of the now First Parish Church in Wayland (Unitarian Universalist), where I encounter one of the George Washington Highway markers from 1932 marking the route of Washington’s 1776 journey to Cambridge as well his 1789 inaugural trip. The church itself, as classic a New England village church as you will find, was rebuilt here in 1814 after replacing a previous version located across the now canalized Mill Brook; this can be seen on Mosman’s map below (the building marked “meeting house”). If the road was not a principal road in the earliest days of the settlement of Sudbury, it was certainly the main road by the late eighteenth century, problematic a road as it may have been. Local historian Helen Fitch Emery notes, in her history of Wayland, that “It turned out that the location of the fourth meeting-house was a low and swampy one. Attempts to drain the lands and roads near the structure with ditches led in 1731 to emergency measures to refill ditches and lay stones around the meeting-house foundation. The village center which grew up around this fourth and the nearby fifth (1815) meeting-houses has continued to be plagued with problems of wetness resulting from its low elevation.”10Helen Fitch Emery, The Puritan Village Evolves: A History of Wayland, Massachusetts. (Canaan, New Hampshire: Phoenix Publishing.), p. 50.

A look at Mosman’s map indicates another important aspect of the old Post Road: it did not continue past today’s Route 27. What today continues as Boston Post Road (Route 20) across the river into Sudbury, did not appear on maps of the area until 1831, when it is listed as the “Worcester Road”. Instead the original road turned north at this point to follow a path to the old bridge over the Sudbury River 1.5 miles north of the Washington marker. This section of the walk, through Wayland Center and the original settlement of Sudbury, proves to be much more interesting and full of breadcrumbs.

Ensign Henry DeBerniere, in his report to General Thomas Gage in early 1775, noted that they were “resolved to go the Sudbury Road, (which was the main road that led to Worcester).”11General Gage’s Instructions of February 22, 1775 to Captain Brown and Ensign D’Berniere, with Narrative of Occurrences during their mission, wrote by the Ensign, 1779, p, 10. This is the principal breadcrumb I have used to reach this point thus far. Mossman’s map of 1795 is also very useful as it labels the current path I am on as the “Post Road from Springfield to Boston”. Now I have located a plaque indicating George Washington’s route in 1789. The breadcrumbs are starting to pile up. Fortunately, the description of the journey of Captain Browne and Ensign DeBerniere is fairly detailed at this point and walking the road only helps confirm that I am on the right track. DeBerniere details setting off for Marlborough in the snow, sometime after 2 p.m. on Wednesday, March 1, 1775: “We found the roads very bad, every step up to our ankles; we passed through Sudbury, a very large village, near a mile long.”12Narrative, p. 11 As I mentioned, Sudbury and Wayland were one town until 1780, when the section of town east of the Sudbury River became the town of East Sudbury. The original settlement of the town was along the eastern edge of the vast marsh edging the Sudbury River, with other parts of town, including the area across the river that is now officially called Sudbury, being settled later. The road along the edge of this beautiful area is called Old Sudbury Road today, and the houses remaining from the Colonial era in Wayland are strung out along a mile or so of road from the complicated crossroads here at the contemporary center of Wayland until they peter out as the road approaches the bridge across the river, much as DeBerniere described.


Detail of a map of Wayland, called East Sudbury until 1835, produced by Matthias Mosman, dated May 21, 1795. This map, like the maps drawn for every town in Massachusetts at the time, was produced in response to an order from June 1794 by the General Court of the Commonwealth of Massachusetts that each town survey the boundaries of their towns; the collected maps were used to make up the first official map of the state. The section above shows the “Post Road from Springfield to Boston”, commencing at right at the border with Weston to the border with Sudbury at left. Four main points to notice: 1. The split with the Old Connecticut Path (OCP) at the Weston border, the OCP heading southwest. Mosman refers to the OCP as “the County Road from Framingham to Boston threw(sic) Weston and Watertown.” County roads were secondary roads of transit, unlike the “Post Road” which was the main road. 2. No mention is made of Plain Road or of any of the putative “oldest roads” of Wayland; these maps generally showed only major roads, implying that Plain Road was not a major road by 1795. 3. The junction of the Post Road with the “county road from Framingham to Concord threw (sic) Lincoln,” in the middle of the map. The junction, today’s intersection of Boston Post Road (Route 20) and Cochituate Road (Route 27/Route 126), occurs before the crossing of a “very small stream,” today’s Mill Brook; immediately across the stream is the “Meeting House” which was located north of Mill Brook until it was rebuilt on the south side of the Post Road in 1815. 4. At this junction the Post Road deviated from the current Route 20, which did not cross the Sudbury River until the early 1800s. Instead the old road followed what is now called Old Sudbury Road to cross the Sudbury River at a point 1.5 miles further north, as discussed in the text below. After crossing the river, the road turned sharply south again and closely followed the current boundary between Wayland and Sudbury until crossing into Sudbury at the site of the Training Field (again, see the main text for details). The full map is available at Digital Commonwealth.


19 Mile Stone, 1768. In front of Wayland Historical Society Grout-Heard House at 12 Cochituate Road, Wayland. Although the distance to Boston from this spot is actually 19 miles along the Old Post Road, this stone is part of another series of stones that follow Old Connecticut Path to Framingham. It was moved here at some point from a location in Cochituate, the southern part of Wayland.

The center of Wayland today is a confusing jumble of roads that spin off in multiple directions. First there is the major east-west artery, Route 20, which is called Boston Post Road. For the first 1.5 miles from the Weston border, this is in fact the original Post Road as I have explained. From the point where Route 20 continues past Cochituate Road (which is also simultaneously Route 27 and Route 126 for a short distance), Boston Post Road is NOT actually the old Upper Boston Post Road, it is a newer road built to create a more direct route across the Sudbury River. A glance at the map above clearly shows that the new road is much more direct (it is 1.8 miles straight across the river as opposed to 2.7 miles along the route of the old road).

The Old Post Road instead turned north through the center of Wayland along Cochituate Road, first crossing the Mill Brook, which currently runs through a culvert under Route 20 but appears again on the opposite side of the road (the small pond I passed earlier) adjacent to the appropriately named Millbrook Road. Very shortly thereafter I encounter a fantastic breadcrumb in the form of an old milestone in front of the Grout-Heard House, the present location of the Wayland Historical Society. The milestone indicates 19 miles to Boston and is dated 1768. It is, however, a red herring! A series of milestones can be found along the route of the Old Connecticut Path through Wayland and Framingham which have distinctive lettering. There is a milestone in front of the Reeve’s tavern building which is hard to read but would be 17 miles from Boston and there is another stone opposite the entrance to Wayland High School which reads 18 miles. A stone for 20 miles can be found two miles down the road in Framingham, also dating to 1768, with the same distinctive letter style. The nineteen mile stone in front of me is clearly the stone missing in this series, a fact also noted by numerous historians of Wayland.13Wayland A to Z, p. 129; Wayland Historical Tours, p.35. I will return to these stones and a discussion of the Old Connecticut path in the next entry.

My mind goes back to Monty Hall as I rue the opportunity to accrue another breadcrumb and discover that in fact this breadcrumb belongs to another trail. Just past the milestone I cross the Massachusetts Central Rail Trail, a new multi-use trail built along the lines of the now defunct railroad. This ambitious project eventually will continue all the way to the Connecticut River valley and link up with trails in Northampton that branch off in many directions. This section continues east to the edge of Waltham, where plans are underway to connect it to trails branching out from Boston and Cambridge, while the western branch continues for roughly 0.6 miles running parallel to Route 20 until it is ends for now at the contemporary Sudbury River bridge.

Almost immediately I reach another difficult crossroad. Two roads branch off at this junction: to the left Route 27 continues as Old Sudbury Road, while Route 126 branches off to the right as Concord Road. I stated above that Old Sudbury Road was the original Post Road, but this is only partially true: the straight 700 feet of Old Sudbury Road from this spot to the intersection with Bow Road was opened only in the 1770s14Wayland Historical Tours, p. 16 Before this the road west to Springfield turned northeast and briefly followed today’s Concord Road before turning left onto the appropriately named Bow Road, which sweeps in a big curve back towards the river before the new and old road rejoin just before the old cemetery on Old Sudbury Road. Thus I have two roads to follow here briefly before they merge into one road again. Should I have chosen road number two back at the Coach Grill and avoided all this complication? My faith in Ensign DeBerniere remains unbowed, however, and I chant my mantra as I continue forward along “the Sudbury Road, which was the main road to Worcester.”

Sheep along Bow Road.

The short stretch of “new” Old Sudbury Road is unremarkable. Apart from the Zacariah Bryant House at #10, built the same year the road opened in 1770 and a pretty farmhouse at #15 from 1830, the main feature of this section of the road is the massive “Wayland Town Center” development that sprawls through what was clearly once marshland along the west side of the road. One truly wonders how stuff like this gets approved in what seems like a town that has a strong sense of commitment to preservation; there are numerous natural spaces set aside in the town as well as what must be fairly strict zoning laws in general as there are very few of the McMansions often encountered in wealthy towns around Boston. It turns out that this is a long and complicated story dating back to the 1950s when a residential development was rejected in favor of allowing Raytheon Corporation to lease the land for a factory!15Emery, pp. 314-315. So the current development is actually an “improvement” on what was there from the 1950s until recently. Still, the 733 to 167 vote of the town meeting in 1954 in favor of changing the zoning laws to allow the large corporation to build a massive research and manufacturing facility on what must have been a lovely site is astonishing in hindsight.

To add an additional ingredient to this already confusing story, the solid Colonial building behind the aforementioned milestone, the current home of the Wayland Historical Society, the Grout-Heard House dating to 1800, parts of which are thought to date as far back as 1740, was moved from its present location to a spot along Old Sudbury Road in 1878 to make way for a new Town Hall, and was subsequently moved back to this location in 1962 after Raytheon erected their campus on land nearby.16Wolfson & Hoyt, pp. 77-79. I am starting to think I have the wrong game show in my head as I walk along; rather than Let’s Make A Deal, perhaps I am on Candid Camera, and a big prank is being played on me. I am sure I am following the Old Boston Post Road, but the “usual facts on the ground” have more frequently turned out to be false promises than useful pieces of evidence.

The fact that the town is called Wayland and not Sudbury is also a source of constant confusion, especially as all references to the area in the Colonial era were to Sudbury and they usually referred to what is now Wayland, as evidenced by DeBerniere’s narrative above. Even this seemingly straightforward name change is shrouded in uncertainty. As I walk along Concord Road towards Bow Road along the putative “earlier” section of the Boston Post Road, I pass the Wayland Free Public Library, which claims to be the first public library, a difficult claim to prove.17Emery, A Puritan Village Evolves, p. 180. Another claim made about the library by A.S. Hudson in his Annals of Wayland , is that “in 1835 the town took the name of Wayland after President Francis Wayland of Brown University, and the generous donor to the public library.”18Hudson, p. 51 Helen Fitch Emery, another researcher of Wayland’s history, claims there is little extant evidence to support the specific claim of Hudson, but that it is likely that the town was in fact named after Francis Wayland.19Emery, pp. 77-78.

To summarize then: I am currently walking along one of two permutations of one of three or four possible roads that may or may not be the original Boston Post Road, despite the fact that there is an additional actual road in the town called Boston Post Road that is for the most part not the actual Boston Post Road, in a town called Wayland that was once Sudbury but is not Sudbury now because Sudbury is the next town and the town called Wayland may or may not be named after a man who may or may not have been given that honor because he donated money to a library that may or may not be the first public library in America, located next to a colonial building that was moved somewhere else then moved back to the original spot nearly a century later, which has a milestone from 1768 sitting on the lawn in front accurately indicating that it is 19 miles to Boston from this spot, except that this stone belongs in a different spot along a different road in Wayland that certainly was the road traveled by the various sources I have used heretofore for my research on the Post Road, indicating that I may be on the wrong road after all! Plus there are game show metaphors, breadcrumb analogies, houses that date to the 1770s that don’t remotely look like they are older than the 1950s, and a giant factory that has disappeared from the center of a bucolic little town to be replaced by a giant shopping mall and a massive housing development, all this located next to a bike trail that used to be a railroad on a road called Old Sudbury Road, the section of which all this is located not being the original Old Sudbury Road at all, which was Concord and Bow Road until 1770. Is it any wonder it is taking me so long to make my way through this four-mile stretch of road?

The original settlement of Sudbury was along this bucolic stretch of Old Sudbury Road in Wayland. The first, second, and third meetinghouse were all located here. After the congregation split into what would eventually become Sudbury and East Sudbury, the meetinghouse was moved about a mile south near to its current incarnation on Boston Post Road, to accommodate the demands of residents in the south of town.

I need some facts to get my feet back on the ground, despite the fact that, by the very definition of this project, my feet are on the ground. First of all, it is obvious as I walk along that Wayland is a wealthy town. If neighboring Weston is the wealthiest town in Massachusetts (Median Household Income according to the 2021 American Community Survey $220,815), Wayland ($203,789) and Sudbury ($217,847) are not far behind.20For comparison, Median Household Income for the state of Massachusetts is $89,645, and for the United States is $69,717. Thus the middle household in Wayland earns nearly three times as much as the middle American household. This trio of towns feature in any list of the dozen or so wealthiest towns in Massachusetts. At the first census in 1790, the town of East Sudbury contained 112 structures housing 801 people. At the most recent census in 2020 there were 5296 housing units recorded, housing 13,943 individuals, indicating that in 1801 an average household comprised 7.2 individuals while today 2.6 individuals reside on average in what appear to be generally large houses. After passing the elegant 1806 Henry Reeves house at #18 Concord Road, a short five minute walk from the junction with Old Sudbury Road, I turn left onto Bow Road. Along this short road are no Colonial era buildings as far as I can judge, but at #17 there is the Elisha Rice house from 1800, and some sheep on the opposite side of a lovely quiet lane lined with charming mostly nineteenth-century houses. Only when I reach the junction of Bow Road and Old Sudbury Road do I finally start to encounter a steady trail of breadcrumbs heading northwest toward the old bridge over the Sudbury River.

The building sitting on a slight elevation above the intersection of Bow Road and Old Sudbury Road, with a commanding view over the woods and fields adjacent to the Sudbury River, is the Josiah Bridge House. Bridge was, from 1761, the minister of the east precinct of Sudbury, and from 1780, the town of East Sudbury, until his death in 1801, and parts of the house may date to the 1740s. Just beyond the house is North Cemetery, the oldest burying ground in Wayland, and the site of the first meeting-house in Sudbury. As is usually the case in New England towns, the location of the meeting-house and its migration over the years is one of the most important clues in understanding the history of the town’s development. This stretch of road leading to the town bridge was the earliest settlement in Wayland. Eventually areas on the opposite side of the Sudbury river were settled, as were areas further south along Old Connecticut Path in what is known as the village of Cochituate.

The only constant in the early New England town was the requirement to attend service. Tensions in New England towns often arose over the difficulty some residents had in attending church services. In the case of Sudbury, the problem was two-fold; the first complication was that the Sudbury River often flooded its banks and the bridge was often impassable, thus frequently complicating the journey for the residents on the opposite bank. This led to what often happened in the evolution of towns, as we have seen in the case of Weston, Waltham, and Watertown, all once one town; the residents of the west side of the Sudbury River petitioned to form their own congregation, which was granted in 1722 and a new building opened in 1723 in what is today Sudbury Center.21 See Emery, Chapter one, pp. 9-29 for more details

The second problem was that, once the parishioners west of the Sudbury River moved out, the parishioners in the southern part of town complained about the distance to the meeting-house. This was finally resolved only by moving the meeting-house south to a spot near Mill Brook, just opposite from the site it is located today on Boston Post Road. The site of the meeting-house from 1726 to 1814 can be seen on Mosman’s map from 1795 above.22See Emery, Chapter two, pp. 30-51, for more details

Inevitably, the separation of the town into different congregations led to the separation of the congregations into separate towns. In 1780 the two congregations became the towns of Sudbury on the west side of the river, and East Sudbury on the opposite side, with a complicated border drawn between the two that we shall soon encounter. In the earlier separation of the congregations, the minister at the time, Israel Loring, somewhat surprisingly decided to join the new congregation across the river, taking the church records with him. When the eastern residents decided to petition for separation from the west, the west had a slightly larger population and the lion’s share of the towns documents, so the east conceded the original name of the town, thus the eventual name Wayland for what was once Sudbury.


From the site of the original settlement of Sudbury the road towards the bridge sweeps northwest, providing lovely views over the open fields and meadows between the road and Sudbury River, along with several hills on the opposite side of the river which will figure significantly in the future entry on the town of Sudbury. Much of the land on the west side of the road is preserved as part of the Wayland Community Gardens, the Cow Common, or the Great Meadows National Wildlife Refuge. After spending a peaceful hour or two birding the fields and woods near the river, I continue my walk along Old Sudbury Road, “the main road to Worcester,” along which I encounter several houses of historical significance. At #71 is the John Noyes House of 1704, and next door at #73 is the 1795 Micah Maynard House, both opposite the Common. A charming house at #83 from 1811 belonged to Samuel Stone Noyes, while the author Lydia Maria Child resided at #91 Old Sudbury Road in yet another lovely early nineteenth-century house.

Soon I reach Baldwin’s Ponds, visible on Mosman’s 1795 map, and named for one of the original settlers of this part of Sudbury. The 1732 Vade mecum tavern list along the Post Road to Springfield lists a tavern at mile 20 from the Town House in Boston in Sudbury owned by one “Balding’s”. In the 1770s a tavern near the bridge was kept by a Loyalist sympathizer named William Baldwin. It seems very likely that this is the same tavern as Balding’s. The distance from Wilson’s Tavern in Weston, which is listed as 16 miles from the Old Town House in Boston, is 4 miles distant from the spot where William Baldwin’s tavern would have been located here along the final stretch of Old Sudbury Road before reaching the bridge across the Sudbury River.

Last version of the old Town Bridge over the Sudbury River. The four-arch stone bridge replaced earlier wooden bridges in 1848 and was substantially rebuilt in 1903 after another flood damaged the structure. A flood in 1955 resulted in the abandonment of the old bridge in favor of a newer straighter road over a new bridge, from which this photograph was taken.

Just before I reach the current bridge over the Sudbury River I find the most exciting breadcrumb of them all along my walk along the Boston Post Road in Wayland. A few yards past Baldwin’s ponds is the entrance to the Wayland Country Club. A small dirt path leads along the edge of the golf course parking lot towards a scrubby area along the banks of the river. To my astonishment I find among the fallen trees and weeds not only an old bridge but a plaque in front of the bridge describing the importance of the bridge to the history of Sudbury and of Massachusetts (see the photograph at the beginning of this entry and the one at left). The bridge has a couple of worn out concrete Jersey barriers in front to dissuade any passage onto the bridge but it is easy enough to scramble over the fallen tree and the barriers onto the bridge. The decaying structure is easy enough to cross and brings me to a small island where I can just make out the old road. After accidentally startling a resident deer resting on the path I continue across the small island to reach the other side, where there was formerly a second bridge across a channel that had likely been carved through to make the passage more direct at some point in the distant path. This “canal bridge” as well as the original town bridge are labeled on Mosman’s 1795 map. One can still make out the pattern of the original road along this short stretch on Google Maps despite the fact the road and bridge ceased to exist after 1955, when flooding destroyed the canal bridge and the state opted to straighten the road and build a new bridge a few yards south of the old bridge and the old road. I have mapped out the route of the old road in my map of the walks in Wayland (the old road is the black line at the top of the map).

Stone marker near the old Town bridge across the Sudbury River. The obverse side lists Sudbury residents who died in King Philip’s War.

As I scramble back over the trees and barriers on my way back to the main road, I stop and take a look at the stone marker near the entrance of the bridge which describes the events which occurred around the bridge during King Philip’s War in 1676, a subject I will elaborate upon in the Sudbury entry. It also describes the history of various versions of the bridge and tells us that “Washington crossed here in passing through the town.” I make my way back to the main road and cross the very narrow and busy Route 27 bridge over the Sudbury River, stopping long enough to get a photograph of the old four-arch stone bridge, built by Josiah Russell, which replaced the last version of the wooden bridge in 1848, although it was substantially rebuilt after another flood in 1903.23For a much more detailed discussion of the Sudbury River and the history of crossings over the river as well as the long relationship with the river of the inhabitants who live near it I highly recommend the online document published by the Wayland Historical Society in 2020 entitled Crossing The Sudbury


Immediately after crossing the bridge, the road to Sudbury center continues straight ahead while the Boston Post Road turns sharply left onto what is today called River Road. There is a landing for launching kayaks into the river here and the road literally brushes against the marsh grass at this point on both sides, with signs indicating that much of it is part of the Great Meadows National Wildlife Refuge. It is remarkably beautiful and peaceful along this stretch of road. River Road was part of the old causeway or “causey”, a built-up pathway that allowed easier passage through this often flooded area. Mathias Mosman, who surveyed the town for a map produced in 1795, describes the bridges over the river and the causeways in detail at the bottom of his map: “Town Bridg (sic) at the long Causey over the Main Stream and another over the Canal and a Causey about 1411/2 rods long about 4 feet high, which is kept in repare (sic) by East Sudbury, excepting the Canal Bridg (sic) and 52 rods of S (unreadable) Causey, which the town of Sudbury keep in repare (sic).” A rod is equivalent to 16.5 feet, so the length of the part kept in “repare” by East Sudbury was almost a half a mile.

John Adams, who passed this way on Thursday June 13, 1771, on his way back from a trip to Connecticut, relates that “As I came over Sudbury Causey, I saw a Chaplain of one of the Kings Ships fishing in the River, a thick fat Man, with rosy cheeks and black Eyes. At Night he came in with his fish.”24Adams Diary, Vol. II, p. 35. Henry DeBerniere, in his description of the visit to Marlborough, notes that “the causeway lies across a great swamp, or overflowing of the river Sudbury, and commanded by a high ground on the opposite side.” On the hasty return of Browne and DeBerniere from Marlborough after realizing they were in grave peril, they “got off without being perceived, as far as the hills that command the causeway at Sudbury, and went into a little wood where we eat a bit of bread that we took from Mr. Barne’s, and eat a little snow to wash it down. –After that we proceeded about a hundred yards, when a man came out of a house and said these words to Capt. Brown, ‘What do you think will become of you now,’ which startled us a good deal, thinking we were betrayed.– We resolved to push on at all hazards, but expected to be attacked on the causeway; however we met no-body there, so began to think it was resolved to stop us in Sudbury, which town we entered when we passed the causeway; about a quarter of a mile in the town we met three or four horsemen, from whom we expected a few shot, when we came nigh they opened to the right and left and quite crossed the road, however they let us pass through them without taking any notice, their opening being only chance; but our apprehensions made us interpret everything against us.”25Narrative, pp. 13-14. Thankfully, my peaceful walks through this tranquil area much more resemble Adams’ description of seeing people fishing than DeBerniere’s alarming tale.

House at the junction of River Road and Water Row in Wayland with stunning views out over the nearby Sudbury River. The house is almost entirely surrounded by the vast Great Meadows National Wildlife Refuge. River Road, which can be seen at the right, was originally known as “the causeway” and is a man-made elevated roadway leading to the bridge over the Sudbury River.

A slight bend in the road brings me to an intersection with Water Row and a lovely old red house at #3 which, according to the Wayland Historical Tour booklet (p.26), “tradition says belonged to John Goodenow. After the first home was burned by the Indians in King Philip’s War, the present one was built within a few years, using some of the charred timber from the original homestead.” Whatever the history, the house commands a beautiful site virtually surrounded by the river and the meadows of Great Meadows National Wildlife Refuge. The house itself is visible in the winter clear across the river from the present Route 20 bridge, a mile away.

The road passes through woods and more water meadows before beginning the incline, almost half a mile from the bridge, to the heights commanding the Sudbury River described by DeBerniere. The hill tops out at a mere 158 feet above sea level, so it is not exactly imposing; compared to the surrounding lowlands around the river, which bottom out at about 123 feet above sea level, the view is impressive nonetheless, so it does feel higher than it really is. At this point the somewhat startling appearance of the Wayland Department of Public Works brings the bucolic phase of the walk to an end. At this point the west side of River Road belongs to the town of Sudbury, and shortly, both sides of the road are part of Sudbury but the road itself is still, confusingly, part of Wayland. On the left is a small field and wooded area which was once the “Training Field” of Sudbury. Since it is now located in Sudbury, I will leave it for the Sudbury entry. At least one property owner along what became the border between the two towns during the 1780 separation of Sudbury from East Sudbury chose to join Sudbury and this required the lines to be drawn in a very curious manner. This involved creating a diamond shape outgrowth from Sudbury into East Sudbury.

Despite the complicated border it is quite clear when I finally leave Wayland and enter Sudbury. First of all there is a sign; secondly, the name of the road changes from River Road to Old County Road; thirdly the quality of the road markedly deteriorates immediately, although it at least has a sidewalk, something there was little of in Wayland; and lastly, there is the abrupt appearance of developments lining both sides of the road including a landscape design company, a housing complex (The Villages at Old County Road!), a tennis club and, most alarmingly, A Herb Chambers BMW showroom, all in the quarter mile from the Wayland/Sudbury border to the place where Old County Road joins Route 20 in Sudbury and the old Boston Post Road and the new Boston Post Road are reunited once again. The Upper Boston Post Road and Boston Post Road (Route 20) are, for the most part, one and the same through Sudbury. So, despite the traffic and development along the road, at least I won’t have to deal with Monty Hall anymore. Most deals involve tradeoffs; in the case of Wayland I got to follow some bucolic old roads (mostly without sidewalks…) but also had uncertainty about the course of the road and which road was the “best” one to follow. In Sudbury I will have more certainty (and sidewalks) but also more traffic and commercial development. For now, I’ll take that deal.

River Road looking south. This was part of the old causeway leading to the bridge over the Sudbury River, a major crossing point along the Upper Boston Post Road. The Causeway was described by visitors such as John Adams and Henry DeBerniere.

Distance traveled in this entry: 4.2 miles (Upper Boston Post Road route only; this does not include all the alternative roads investigated while researching this entry)

Total Distance traveled along the original route of the road from the Old State House in Boston for this project: 21.6 miles.

Total Distance covered for all the walks described in Boston Rambles: 61.5 miles

5 Responses to Wayland, Massachusetts: Waylaid in Wayland

  1. The red house on the corner of river rd and water row was moved to its current location in 1804. At that time there was a thriving hostelry across the street. The house was moved from the corner of water row and rt 27 where there is still a cellar hole. At the time it was moved it was a small saltbox style house. ca 1830
    Prior to 1804 the house was owned by various members of the Rice family. The first owner at the current location was Thomas R Plympton, who eventually made a fortune in waltham real estate.
    Prior to 1804, there had, as I recall, been a blacksmith shop on that site, at the head of the “long causeway.”
    I owned that house for many years, and was encouraged to research it by my mother Helen F Emery

    • Thank you so much for this information. The “red house” was a bit of a blank spot for me as I walked through this lovely area. I wasn’t really sure the information about it that I had read was accurate so I just passed on a little of what I had found and let it go at that.

      It is such a lovely house in an astonishingly beautiful area; how fortunate for you that you were able to live there! I now have the honor of receiving useful information about Wayland from two members of the Emery clan as your mother’s book was very helpful in the preparation of this essay about my walks through Wayland along the Upper Boston Post Road as well as my walk along the Framingham Road.

      I posted your comment at the bottom of the entry so that any future readers might have access to your informative addition to the history of the road.

      All the best, Gary

  2. […] 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 […]

  3. In the Town Records is a letter from Rev. Francis Wayland’s son after the Reverend’s death saying how pleased his father was that the town was named after him. Also the money for the library was given some time later, not when the town changed its name nor as a bribe to call it Wayland. The money was to promote a library building in 1850’s.

    The reason the original Sudbury was FORCED to take the name East Sudbury was because the first two or three times the west side of the river petitioned for a split, the east side argued against it and the council denied the split. the southern portion of Wayland today was not part of the original Sudbury Plantation. It was four grants given by the Commonwealth to individuals – Dunster, first president of Harvard, Mrs. Glover because she brought over the first printing press (actually her husband planned the trip, got on the ship but did not survive the journey and died aboard ship, thus leaving his wife and children to continue the task at hand) The printing press was housed at Harvard. while neither Glover or Dunster ever lived on their grants, they did rent the land to Edmund Rice. (Glover and Dunster eventually married but her land went to her children, not Dunster). The other two grants went William Jennison and Herbert Pelham.

    Now as to why the original settlement lost rights to the name “Sudbury” was because the east side finally petitioned for the separation. The General Court made a rule that whoever petitioned for separation from the founding community would lose the right to the original name and records. Hence the east side became East Sudbury and were forced to give all their records to the west side which continued to be known as Sudbury. Just as did Weston (formally Watertown Farms) and Waltham (formally West Precinct) have to choose a new name and did not receive any of records for the people living in that area prior to they separation from their mother town, Watertown. (The penalty for not allowing the west side to leave when they petitioned for separation for they would have been known as “West Sudbury.” Maybe?) East Sudbury later copied all the records to be kept for their own records since most of the records occurred in what is known as Wayland today.
    Wayland Library is the first legally town supported library in Massachusetts. The voted before Boston to support the library but was advised to until the legislature approved the legality of the town using tax funds for such a project. Wayland waited and voted a second time after the legislators voted it into law, a month before Boston did and they opened their doors to the community before Boston did. Judge Edward Mellen, expressed doubts about the Town’s right to tax for library support. As a result, Rev. Wight, a Representative in the General Court and Wayland citizen, introduced a bill which resulted in the Library Act of 1851 making it legal to raise and spend public funds in order to “establish and maintain libraries for the use of the inhabitants thereof.”

    • Thank you so much for reading this and for providing clarification regarding the history of the naming of the town and the history of the library. As someone passing through the town, my main focus is on the route of the roads and their development. I appreciate that I am liable to get the details of the history of the town muddled, so any feedback is greatly appreciated. Any additional information about the history and development of the roads in the town would also be welcome.


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