Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Weston, Massachusetts: The Myth of the Wild Weston

Upper Boston Post Road Entry #4 (UBPR #4)

Golden Ball Tavern, Weston, Massachusetts. This photograph was taken on February 27, 2019, 244 years almost to the day that Captain William Browne and Ensign Henry DeBerniere visited during their spy mission in the “wild lands” west of Boston. The spies stopped here on the evening of February 23, 1775, after finding the landlord Isaac Jones to be “a friend to government.” They departed for Worcester the following morning and returned to the tavern on February 28. On March 1, 1775, the two men spent a long day walking along the Boston Post Road to Marlborough but were forced to return as they had been discovered, completing what they calculated as a 32 mile round trip march in the snow through what is now Sudbury and Wayland to spend a final night at the tavern, before returning to Boston the next morning. All photographs by the author.

“It was my dream that screwed up, the stupid hearthside idea that it would be wonderful to follow one great red line across America…”

Jack Kerouac, On The Road, p. 13.


There’s no @*&# sidewalk! Standing on the busy edge of Route 20 next to Dunkin’ Donuts and a Mobil Gas Station in the freezing cold as a stiff late winter wind smacks me in the face and the traffic speeds past entering and exiting Interstate 95, I realize that the sidewalk is on the other side of a four-lane road with nary a crosswalk or a traffic light in sight. As I contemplate how I am going to cross the road without getting killed on the first real day “on the road,” the first day I cannot reach the starting or end point of my walk using the T (short for MBTA: Massachusetts Bay Transportation Authority), the first time I have left my comfort zone inside Route 128, otherwise known as Interstate 95, the ring road surrounding the city of Boston and the densely populated inner suburbs (this website is called Boston Rambles after all, and we are unofficially no longer in “Boston“), I am put in mind of Sal Paradise’s similarly glum beginning to his own mythical adventure.

An inauspicious start to my adventure in the wilds of Weston.

Sal (Jack Kerouac) hits on the idea of hitchhiking from Manhattan across America to reach San Francisco and sets out on public transit north to Yonkers, at the edge of the densely populated suburbs of New York City, from where he attempts to hitch up the Hudson River Valley the remaining 25 miles or so to reach Route 6 at Bear Mountain and then head west on “one great red line across America.” However, the traffic is thin on the ground, it pours with rain, he gets soaked and “looked like a maniac,” making it even harder to get rides. Upon finally reaching his destination and finding little or no traffic he realizes Route 6 is merely a road that “disappears into the wilderness,” so he returns to New York City and takes a bus to Chicago.

I have hit upon the quixotic idea of walking along the Boston Post Road west across Massachusetts and then south through Connecticut to New York, and my inaugural experience so far is underwhelming. I took MBTA bus #70 as far as I could in Waltham and then walked one and a half miles along Weston Street, through the cloverleaf interchange snarl of Interstate 95 and US Route 20, and ended up here, stuck on the edge of the highway, next to a gas station, on the side of a very busy road with no sidewalk. As I contemplate the comparative luxury of a bus ride back home, I am pulled from my self-pitying reverie by the polite tap on the horn of a kindly woman who has realized I want to cross and has slowed her car to allow me to pass in front of her as she holds off the raging bulls behind her, and I gratefully make my way across this inauspicious beginning of Boston Post Road, as the road I am traveling is now officially called here in Weston, Massachusetts.

The busy, four-lane road at the intersection with Route 128 quickly becomes an even busier two-lane road but at least there is a mediocre sidewalk running along the north side of the road, covered with the debris left from the snow banks pushed here over the course of a winter of snow plows traveling this same road. Since I am not hitchhiking, the presence of so many cars is unwelcome. So far, my trip out of the city does not feel very wild (traffic excepted), or rural, or even pleasantly suburban, as I had anticipated in Weston, one of the wealthiest towns in Massachusetts. The noise is made worse by the fact that there is an embankment on the side of the road that catches and amplifies the roar of the traffic. This feature of the road was recorded on a map made in 1775 by the spies Captain William Browne and Ensign Henry DeBerniere as they passed through this spot on their way to temporary safety at a tavern a little further down the road in Weston. The map specifically shows a “defile,”1A defile is a narrow passage, generally between hills, cliffs, or rocks. General Gage, in his orders to Browne and DeBerniere, specifically stated that “all passes must be particularly laid down, noticing the length and breadth of them, the entrance in and going out of them, and whether to be avoided by taking other routs (sic)”. General Gage’s Instructions of February 22nd, 1775, to Captain Brown and Ensign D’Berniere, with a curious narrative of occurrences during their mission, wrote by the Ensign. Boston: J Gill, 1779, p. 3. Hereafter referred to as Gage’s Instructions. three quarters of a mile in length from what is likely today’s Summer Street to the point where Boston Post Road crosses today’s Three Mile Brook, which still corresponds to the actual distance between these two points. The road in this area today certainly defiles my idyllic preconception of what the Boston Post Road would be like once I escaped the 128 Ring and reached the wilds of Weston. Yet it is the actual road, as I know from detailed examination of maps ranging from that of DeBerniere (he was the actual surveyor) to the present.

Detail of map produced by Ensign Henry DeBerniere in the late winter of 1775, showing the Weston portion of their survey of the area west of Boston. Note that the map is oriented so that east is at the left and south is at the top. At left is Stony Brook, the border between Waltham and Weston. Note the “defile” running from the first road (presumably today’s Summer Street) leading off of the main road to the “creek,” today’s Three Mile Brook. At right, upon entering what is now Wayland, the main road splits into the “Road to Framingham,” which is the Old Connecticut Path and the “Road to Sudbury,” which is the Boston Post Road. “Colonel Jones’s” refers not to Isaac Jones, landlord of the Golden Ball Tavern, which was located directly on the Boston Post Road, but to Isaac’s cousin Elisha, a colonel in the militia and Loyalist who fled to Boston as many Tories did, Isaac Jones being a notable exception, after the Battle of Lexington and Concord on April 19, 1775.


That this is indeed Boston Post Road and not some imaginary early twentieth-century concoction dreamed up by nostalgic zealots eager to celebrate the ideals of the early American Republic is a constant source of worry. On my walk to New York a few years ago along the Lower Post Road I often encountered roads called Boston Post Road that were not, and never had been, a Post Road. These “Post Roads” were often so-named in the early twentieth century, not coincidentally with the upsurge in the use of automobiles as a form of travel, likely by local boosters trying to encourage and to cash in on Americana nostalgia road trips. There was a widespread revival of interest in the early history of the United States2See for example this museumstarting in the late nineteenth century and accelerating in the first three decades of the twentieth century, which manifested itself in architecture, specifically the style called Colonial Revival, as well as in a surge in the restoration of neglected buildings from the Colonial and early Federal periods and even the wholesale “reconstruction” of “villages” such as Old Sturbridge Village or Colonial Williamsburg. The nostalgia for early America can also be discerned from the abundance of publications from the early twentieth century on topics such as genealogical research, olde taverns (yes, that spelling, often accompanied by a Ye !), stagecoach travel, and even old roads, including the Old Boston Post Road.

Map of Weston by Jonathan Kingsbery produced in 1795. Courtesy of Massachusetts Archives. Notice the prominence of the “Post Road to Springfield”. Also note the “Bridge” over “Stony Brook” near the “saw mill” and “grist mill” at far right, as well as the “grist mill” on the curved part of the road between Stony Brook and the “meeting house,” today’s Crescent Street discussed in the main text. Kingsbery states in the text at the bottom of the map that “The reputed distance from the Metropolis of the Commonwealth to the center of said town in the road usually travelled is fourteen miles.” He also indicates a “13 mile stone” between Stony Brook and the Meeting house, which today would be just before the Crescent Street turn. I found no evidence of such a stone on my walks unfortunately. My walk along the original route covered a distance of a 14.5 miles to this same point, as the opening in 1793 of the West Boston Bridge over the Charles River shortened the distance by 1.5 miles. Kingsbery also surveyed the nearby towns of Brookline, Newton, and Needham for the state in the same period. Finally, I use Kingsbery, and not “Kingsbury,” because that is how it is spelled on the maps that he signed.

The genesis of this project is, in part, a reexamination of one of these books, The Old Boston Post Road by Stephen Jenkins, published in 1913.3Stephen Jenkins, The Old Boston Post Road. (New York: G.P. Putnam & Sons, Knickerbocker Press, 1913). As my original project focused on the road running south from Boston to Rhode Island then west across Connecticut, a route Jenkins did not travel (he went from New York to Boston along the Upper Boston Post Road, the road I am currently writing about), I read his book but did not utilize it much. Jenkins was, unsurprisingly, a product of his age, and the book is full of cringe-worthy stereotypes about “Noble Savages” and “buxom serving girls.” Having said that, Jenkins, unlike many modern historians, actually traveled the road, stopping along the way to examine the remaining artifacts as well as providing a brief history of each town through which the road passes. So too will this project; I too will be judged (likely in real time rather than a century later) as a product of my age, race, gender, economic background, and so on. I will try to hide my biases as best as possible and to be aware of alternative viewpoints but essentially my goal is to write about what I see on the road in 2022 and to compare that with the descriptions of Jenkins and another traveler along the road in the early 1960s, Stewart H. Holbrook.4Stewart H. Holbrook, The Old Post Road: The Story of the Boston Post Road. (New York: McGraw-Hill, 1962).

This is the Boston Post Road to most people. This road has received the most attention, and I fear will be lined with kitsch and mythology. While I will tell many of the same tales told by my predecessors, I hope to examine them more critically, because the mythology of the road, historical memory, is also an artifact of the road. Much like the myth of the “Wild West,” much that is in print about the Post Road is legend, not fact. Despite Maxwell Scott’s famous dictum in The Man Who Shot Liberty Valance, I am interested in printing the fact. Although I will discuss the stories that have been told about the Post Road, my primary interest is in the actual road itself. What was the Boston Post Road? What was the route of the Boston Post Road? What is left of the Boston Post Road? This adventure might well be called, pace Kerouac, About The Road.

The principal objective of both my first project and this project is to document the actual road as it existed in the Colonial and the early Federal periods, how it changed, and as it exists today. Some pieces of the Lower Post Road, the road I wrote about in the first project, have been lost forever, but surprisingly, most of the original road still exists. Often the road has been straightened to a degree or large sections have been bypassed in favor of a more direct or wider road, but there are many extant remnant pieces, usually perfectly usable roads that time has forgotten. These appendices are typically very interesting as, having been rendered obsolete as a part of the main thoroughfare and literally bypassed, more of the original architecture has often been preserved. Any success I have had in piecing together the fragments of the original road has come from slowly walking the original route as closely as possible, keeping my eyes open, taking advantage of the knowledge of locals to guide me, and spending a lot of time looking at maps from different eras to see what has changed over time. I have tried thus far and will continue to try to follow the same methodology on the Upper Boston Post Road to map the road that was as well as to describe the road that is.

Detail of a USGS Topographical map from 1950, the “Natick Quadrangle,” showing the Boston Post Road in Weston. Note that in this map north is at the top and east is to the right. Visible at right are the train tracks and Stony Brook converging at Sibley Road. Route 128/ Interstate 95 has yet to be built. Also visible is the crescent shape of Crescent Road, a bypassed section of the original road , just above the word “POST.” A little further west, Boston Post Road passes through the center of Weston then reconnects with the main road, US Route 20, at the junction with a bench mark (BM) at 195 feet. Boston Post Road and Route 20 continue west as the same road to the border with Wayland (at BM 206) on the far left of the map. See my map below of the original route of the Upper Boston Post Road through Weston for more details. Incidentally, Route 20, which begins in Kenmore Square, continues west to the Pacific Ocean at Newport, Oregon. A road trip for another day.


The fun part of following the route of the Boston Post Road. A section along busy Route 20 in Weston.

A good deal of the walking on this project is through areas that have been developed beyond recognition or that are somewhat unpleasant. This noisy section of the walk, leading directly from an exit ramp of a major interstate highway, is not as bad as some areas I have walked, but it is not great either. There are one or two interesting houses to distract me, including the building at 177 Boston Post Road, which was likely originally a farmhouse that was expanded around 1807 purportedly to become a tavern that never was owing to the cost of the expansion, and is now part of the Gifford School,5Pamela W. Fox, Farm Town to Suburb: The History and Architecture of Weston, Massachusetts, 1830-2020, 2nd edition revised. (Portsmouth, NH: Peter E. Randall, 2020), p. 299 but my main thought is that I hope this doesn’t go on for too long. The growing sense of irritation at the cold, at the traffic, at the noise; the general feeling of doubt already creeping in that this project is not going to plan, that Weston is not what I had hoped for, that this whole thing was a dumb idea, as well as my grandiose comparisons with Kerouac, quickly abate as I encounter one of the now bypassed sections of the old Boston Post Road.

As I described in the previous entry, the original Boston Post Road in Waltham crossed Stony Brook into Weston along what is today Sibley Road. This original route is today impossible to follow as the path is blocked by the tripartite barrier comprised of the fenced MBTA Commuter Rail tracks, the looming behemoth that is the Interstate 95 (Route 128) Exit 41 complex, and the diminutive but at present un-bridged Stony Brook. The road begins again on the Weston side of the barrier as a dead-end lane leading off Route 20 to, among other things, the Weston Shooters Club. Although it does not show up on Google maps, this rump road is, like its orphaned sibling on the Waltham side of the “Great Divide,” called Sibley Road, after Nathaniel Sibley, whose mills and factory buildings lined this stretch of the original post road for much of the nineteenth century.6Daniel Lamson, History of the Town of Weston 1630-1890, (Boston: George Ellis, 1913), pp. 160-161. Sibley Road inclines steeply to join Route 20 just beyond the Dunkin Donuts/Mobile Gas station where I found myself at the start of this walk.

Looking east in Weston. Crescent Street at left is the original route of the Boston Post Road. At right is a bypass road built in the 1860s, now part of busy Route 20, in a rare quiet moment.

For the next half-mile in Weston the original Boston Post Road and the current Route 20 are one and the same, after which a right turn off the busy main road leads into the tranquil lane that is Crescent Street. Route 20 continues along a more direct bypass road built in 1860, but I turn right.7Fox, p. 288. Also a comparison between Walling’s map of Middlesex County from 1856 and Walling’s map of Middlesex County of 1866 show that the bypass was built sometime in between the two maps. Immediately the traffic ceases, the road narrows, and charming residential buildings spanning two centuries line both sides of the road; for the first time I have the sensation that little has changed in the past two hundred years along the Great Country Road, as the Post Road west of Boston was sometimes called. This project might be a great idea after all!

Of course the idea that the tranquil lane of today was ever thus is somewhat illusory. The idea that the country is tranquil has always been more of an urban myth, an idealization of a place seldom visited in reality by city dwellers. As Pamela Fox points out in her magisterial town history,8Pamela W. Fox, Farm Town to Suburb: The History and Architecture of Weston, Massachusetts, 1830-2020, 2nd edition revised. (Portsmouth, NH: Peter E. Randall, 2020), pp. 288-92. even this little street, which runs alongside Three Mile Brook, was lined with a succession of “small industries” powered by watermills for much of its history. A grist mill is shown along what is now Crescent Street on Jonathan Kingsbery’s map of 1795, one of the earliest maps of Weston (see above). Indeed some of the charming buildings lining the street, for example 27 Crescent Street, were built originally as tenant houses for workers at the mills.9Fox, p. 303. the house itself was moved to its current location from its original location a little further down the road. Things are never as tranquil, and landscapes are never as unchanging as we would like to believe.

Crescent Street, Weston. The house at left was built by Abraham Sanderson (c. 1804). My “hearthside idea” of what the Boston Post Road would resemble.

It is much more pleasant to walk along Crescent Street than along the first half mile of the post road from Dunkin Donuts. Although none of the buildings date to the visit of Browne and DeBerniere or appear on Kingsbery’s map, the houses are charming all the same, none more so than the Abraham Sanderson House (c. 1804), with its lovely gardens tumbling down a slope to one of the ponds created by damming Three Mile Brook. As the traffic from Route 20 is now merely a distant roar, it is possible to chat with the locals along this stretch of the post road, and the current owners of the house are generous with their time and clearly appreciate the historical value of what they have.

Crescent Street, as the name implies, is crescent-shaped, and after a third of a mile reconnects with Route 20. This second walk along busy Route 20 is a mercifully short 200 yards before Boston Post Road again turns right and leads into the historic center of Weston. The busy main road that I have been walking along for most of my time in Weston was substantially rebuilt in the early 1930s. At the junction of Wellesley Street, Boston Post Road, and Three Mile Brook, the road that is now Boston Post Road Bypass, was pushed through a swampy area south of the town center in an effort to divert traffic.10Fox, p. 134. The next 1.3 miles of Boston Post Road through the historic center of Weston largely avoid the noisy traffic of the sections I walked in Watertown, Waltham, and most of the first mile in Weston. It turns out that the idyllic village green of this most interesting section of the road in Weston has also been rebuilt.


A bypass road was built in the 1930s as part of a master plan to keep Weston Center “semi-rural.” Thus the traffic of Route 20 continues through what was once a swampy area while Boston Post Road passes through the genteel center of Weston.

That roads change is an axiom of this project. A map of the Boston area from 1829 by John G. Hales marks the junction of Wellesley Street and Boston Post Road as thirteen miles distant from the State House in Boston, while Jonathan Kingsbery’s map of Weston from 1795 (see above) shows a “13 mile stone” at a point just before the original Boston Post Road curved north along today’s Crescent Street, half a mile back along the road, a stone I searched for but, unsurprisingly, was unable to locate. Google Maps (June 17, 2022) calculates the shortest walk to Hales’ thirteen mile mark at 12.6 miles. Incidentally, the straight line distance between the two points is 11.8 miles. However, the distance required to trace the original route of the eighteenth century today, the walk I have actually done to get from the Old State House to this point along the Boston Post Road in Weston, is closer to fifteen miles! Most of the difference between the earliest route and the distance between these two points today reflects the building of bridges across the Charles River. The West Boston Bridge (now the Longfellow Bridge) for example, which was completed in 1793, shortened the distance by about 1.5 miles, hence the location of Kingsbery’s 13 mile stone (the distance to the same spot as Hale’s thirteen mile mark on Kingsbery’s map would be about 13.5 miles). Further road modifications and bridge-building account for the shorter thirteen mile distance recorded on Hales’ map of 1829. It is interesting to note that the distance has not become appreciably shorter in the intervening two centuries!

Any changes to the road are far surpassed by changes along the road. The road in Weston was once lined with farms, thus the seventeenth-century appellation for this area, Watertown Farms, which also reflected the fact that what is now Weston was once a part of Watertown. Yet the town has had many identities, one of which, as a place for the estates of the wealthy, soon becomes apparent. As I proceed down yet another tranquil section of the Boston Post Road, I notice elegant textured concrete walls lining both sides of the street. I soon come across a majestic entrance gate as well as a similarly impressive gated stairway that appear to lead into the woods. Subsequently I discover that virtually all of the land on both sides of Boston Post Road for a third of a mile, from the lovely ponds of Three Mile Brook to the First Parish Church, was once part of a large estate called “Haleiwa,” Hawaiian for “beautiful place,” built for Horace Sears, a wealthy businessman, Weston native, and son of a minister of the nearby First Parish Church.11Pamela Fox devotes a whole chapter in her history of Weston (Chapter 14, pp. 309-325) to a detailed description, along with photographs, of the astonishingly lavish mansion, the extensively landscaped property, and the history of the Sears family. I was interested in the name of the estate and had a look at some Hawaiian dictionaries. Apparently ‘Hale’ means house or place and ‘Iwa’ means frigatebird. In Hawaiian culture a frigatebird has a secondary connotation of being ‘pleasant to look at’. Perhaps Sears visited Hawaii, possibly staying at the Hale’iwa Hotel in Oahu, which opened in 1898.

Gate to nowhere? Boston Post Road is lined with concrete walls from the Bypass road almost to Weston Center that were all once part of the grand estate of Horace Sears.

Today a large ranch house from the 1950s sits on the site of the former mansion. Except for a couple of nineteenth-century houses which were part of the estate, the walls seem to be the sole artifact remaining along the road to Weston center, which is otherwise mostly lined with woods. The most prominent building today is at the corner of Boston Post Road and Bypass Road, the large Colonial style St Peter’s Episcopal Church (1957-59). Apparently the congregation was unhappy with the original more contemporary design and went for traditional instead.12Fox, p. 322.

Weston’s history, in broad brushstrokes, is essentially that of a rural farming town with some small industry which also became, by the nineteenth century, the home of quite a few large estates, perhaps not as resplendent as the Sear’s property, but certainly elegant ‘country’ homes for quite wealthy families.13 Pamela Fox dedicates a chapter to “the Estate era” of 1890-1915, and the book is filled will extensive descriptions of individual properties. The tranquility of this lightly populated farming town (1,834 residents in the 1900 Census) was certainly an attraction, as were the low tax rates on property, but another factor was the convenience of transportation options. Three train lines ran through the town at regular intervals, and, of course, the Post Road ran through town directly from Boston. In the late nineteenth century, the city of Boston could be reached in half an hour by train, and with advent of the automobile in the early twentieth century, the trip by car took about the same amount of time.

It is interesting to think that the same convenient location of Weston along the Post Road that led to the presence of many taverns, as we shall see, was also responsible for the transformation of Weston into a home for wealthy residents. The key similarity was the length of time it took to get from Weston to Boston. In 1800 for example, fifteen or sixteen mile’s travel with a wagon of goods was a full day’s travel. Even travelers on horseback would need to rest and to eat, and Weston was a perfect stopping point en route. Our fellow travelers, the spies Browne and DeBerniere, left Boston on February 23, 1775, followed on foot the same route I have walked, and stopped the first night in Weston, at the Golden Ball Tavern, just down the road. An easy car ride, a significantly longer, but not impossible, walk. The time it took to travel the route from Weston to Boston has changed and with it the nature of the travelers: from an overnight stopping point for farmers, salesmen, soldiers, and spies, to commuters who can afford the prices that such a handsome town can command.


First Parish Church, Weston. Note the curious placement of the clock. Built 1887-88 by the architectural firm of Peabody and Stearns.

The Sears estate may be gone, but Weston remains a very wealthy town. Indeed, by some measures, Weston is the wealthiest town in Massachusetts. Immediately after passing the former Sears estate property, Boston Post Road intersects with Church Street and School Street, the historic center of Weston. That the area around the town common flanking the north side of Boston Post Road in the center of Weston is a textbook image of a classic New England town is probably both the reason the town is so wealthy and the result of the wealth of the town residents. A recent $18 million revitalization project has made the area around the town common even more appealing, with utilities moved underground, upgraded sidewalks and new pocket parks, as well as a new “Arts and Innovation Center” in the old library building and a restoration of the Josiah Smith tavern (1757 with additions in 1805).

The tavern operated from the 1750s until 1838, one of many taverns that once lined this stretch of the Boston Post Road in the Colonial and early Federal periods, after which it became a residence. Plans are apparently in the works to permit a restaurant to operate here in the near future, which would return the building to its eighteenth-century roots. In typical New England fashion, the tavern is located across the street from the First Parish Church, which, as is the case for many New England towns, is the principal reason for the existence of the town in the first place, the church in Watertown being deemed too distant for the residents of Weston to reach every Sunday, particularly in the winter. Sixty years after the first English settlement of the area, the residents of the “Westernmost Precinct” of Watertown began to hold services in their own parish church building, and became a separate town in 1712/13.14Lamson, pp. 4-5. See also Fox, pp. 2-3. The current building, which sits on a small rise in a prominent position at the east end of the town center at the junction of Boston Post Road and Church Street, was built in 1887-88 and resembles an old English country stone church, a nostalgic nod to the ancestors of the original settlers of Weston, who left England in the first place to escape the very tradition which the stone church recalled.

The town common, despite appearing as if it has been around since the original church in Weston was raised, is little more than a century old. In 1911, as the bicentennial of the town approached, an improvement plan was proposed and the landscape architect Arthur Shurtleff was hired to redesign the town center. One of the specific goals of the Improvement Committee was “the attainment of a village common or green, always found in the best types of old New England villages.”15Fox, p. 347. The center of what is today a lovely bowl-shaped green swath of parkland was, in 1911, swampland. This was not considered fitting for a town as prestigious as Weston, and Shurtleff himself warned of the dangers of having wild, unkempt wetlands in the middle of town: “This plan would…head off the growth of a slum district in the wetland behind the present town hall.”16Fox, p. 348.

Looking east in Weston Center. Boston Post Road is at right. At left is the Town Green, designed in the early decades of the twentieth century. In the foreground at left is a stone marker commemorating the passage of Henry Knox and his train of artillery from Fort Ticonderoga to Cambridge, latest in a series I have previously passed along the road in Cambridge, Watertown, and Waltham .

Thus the “Archetypal New England Town Common” of Weston was designed specifically to look like the “Archetypal New England Town Common”! One of Shurtleff’s earliest projects was the landscape design of Haleiwa, and Horace Sears likely had some influence on the choice of architects. Shurtleff also recommended shifting traffic out of the town center by construction of a bypass road, as mentioned above, augmenting the sense of unchanging tranquility that even now is characteristic of the town common. As someone who has walked portions of the road that are as traffic filled as is possible as well as this bucolic stretch along a “classic” New England village green, I am understandably less bothered by the manufacturing of a seemingly timeless scene. But it is mythmaking, and it is perhaps unsurprising that the chief designer of both Sturbridge Village and Colonial Williamsburg was none other than Arthur Shurtleff, who changed his name to Shurcliff in 1930, because of “his personal concern for historical accuracy…to conform to its ancient spelling.”17

Even the name of the road that is the subject of this project was changed in 1926 from Central Avenue to Boston Post Road, presumably out of the same “concern for historical accuracy.”18Fox, p. 147. At least this was the actual Boston Post Road. The discovery of this fact slightly dampens my initial enthusiasm at having finally reached a stretch of the original road that was actually called Boston Post Road. I begin to wonder which is more authentic: a renamed Boston Post Road with a town green designed to look like a classic village green in place of what was a wetland in the eighteenth century, or Main Street in Waltham, to use the most recent town through which I passed as a counter-example, with its unending stream of commercial buildings and heavy traffic livened up by the occasional appearance of an eighteenth-century building like the Hager-Mead house of 1795, with its ugly sign advertising the insurance agency that now uses the building? The answer is, of course, both are authentic representations of the changes to the Boston Post Road over time. It is not my job to judge, just to observe and to document what I see as best I can.

Permanent residents of Boston Post Road

Waltham and Weston are neighbors, separated by the Great Divide of Route 128, but also separated by their unique histories, despite both originally being a part of Watertown. Waltham was close enough to Boston to benefit from early industrialization, grew rapidly in the nineteenth century, and is now a diverse and densely populated inner suburb of the city (60% White-Not Hispanic, 17% Hispanic, 7% Black, 12% Asian and 4% Other Races or Ethnicities or Multiracial according to the 2020 US Census), still tangibly part of the city, as illustrated by the ability to reach most of its neighborhoods using MBTA buses. Weston developed differently; far enough away to develop at a slower pace, fortunate in its setting to attract wealthy residents (74% of whom identify as White-Not Hispanic in the 2020 Census, 16% Asian, and all other groups making up the remaining 10% of the population) who contributed greatly to maintaining an image of a town unchallenged by modernity. Despite rapid relative growth since World War II (the population of Weston has almost tripled since 1940 to 11,851 residents in 2020, compared to 65,218 for Waltham in 2020; population density is even more strikingly divergent: Weston 690/mi2 versus Waltham 5,118/mi2), Weston has managed to maintain its position as a wealthy town and has yet to succumb entirely to the unceasing demands of commerce for more chains, more box stores, more malls, more everything. I don’t want to make too much of this point, but the geographical location of these two “sister” towns along the Boston Post Road has resulted in dramatically divergent fates, which can be summed up in two images from my walks; on my most recent visit in May, there were at least a half dozen people loitering on Waltham common who undoubtedly suffer from substance abuse and/or mental health problems, while on a sunny June day children chase large soap bubbles across Weston common to the strains of a band playing Baby Shark. Nobody is sleeping on the benches (curiously, there are only two!) or is sprawled on the ground passed out; the “slum district” never had a chance.


The Josiah Smith Tavern is one of the few survivors of the many taverns that were to be found along this mile-long stretch of the Boston Post Road in the eighteenth and early nineteenth century. Daniel Lamson, in his History of the Town Weston, states that “There were few houses of any importance in all these years that had not first or last served as taverns. It was the most profitable business of all country towns along the main arteries of travel.”19Lamson, p. 190. Lamson also tells us “the oldest record of a tavern in Weston is that of Thomas Woolson, who settled in the town in 1660…(and) kept a tavern from 1685 to 1708…Thomas Woolson, his son, succeeded his father in the tavern…In 1737, Isaac Woolson, who succeeded his father, Thomas, in the tavern, petitions the Court of General Sessions, praying that his license may be continued to him, as he has moved his house some distance from the original site.”20Lamson, p. 188. Pamela Fox locates the tavern near the Concord Road around 625 Boston Post Road, where it operated until about 1762, ceasing “to be a tavern when purchased by Isaac Fiske in the 1810s. Destroyed by fire in 1890.”21 Fox, p. 4.

Josiah Smith Tavern and Barn, originally built in 1757 with later modifications, has recently undergone a restoration. The building served as a tavern into the 1830s before becoming a residence. Plans are in the works to have a restaurant as one of the tenants.

The Vade Mecum for America, an early guide to roads in America and the facilities to be found en route, published in Boston in 1732, lists a tavern in Weston called “Wilson’s” at a distance of seven miles from the previous tavern “Larned’s at Watertown-Mills” and sixteen miles from the Town House in Boston.22Thomas Prince. The Vade Mecum for America; or, a Companion for Traders and Travellers (Boston: Kneeland and Hancock, 1732), p.198. “Larned’s” in Watertown-Mills, which the guide lists as seven miles from the previous tavern “Shippey’s” in Roxbury, and nine miles from the Town House, was adjacent to Watertown Bridge over the Charles River. The distance from what is now the Old State House in Boston to Watertown bridge along the original eighteenth-century route is almost exactly nine miles, while a seven-mile walk from Watertown bridge along the original route brings the traveler to the center of Weston, a total of sixteen miles from the Old State House. “Wilson’s” and ‘Woolson’s” are clearly one and the same tavern. Although the location of the tavern after 1737 appears to have been “some distance” from the original site, it must have been located somewhere nearby along the main road, as the Vade Mecum lists it as seven miles from Larned’s. Incidentally, the distance from Watertown Bridge to Concord Road (625 Boston Post Road) along the route of the original road is 6.8 miles.

Boston was one of the three largest towns in the colonies before the Revolution and was the largest until the 1750s. The town was a major destination for travelers from New England as well as from other colonies. Although travel by sea was more common for long distance voyages, many travelers used the relatively poor roads of the colonies to travel long distances. For example, Alexander Hamilton, a physician from Annapolis, kept a journal of his travels by horseback to Boston in 1744, although he used the Lower Post Road for that journey.23Alexander Hamilton, Gentleman’s Progress: The Itinerarium of Dr. Alexander Hamilton, 1744. edited by Carl Bridenbaugh. (Pittsburgh: University of Pittsburgh Press, 1948). Other travel narratives from the eighteenth century include those of Sarah Kemble Knight in 1704, and James Birket in 1750; both travelers also followed the Lower Post Road.24Sarah Kemble Knight, The Journal of Madam Knight in Colonial American Travel Narratives, edited by Wendy Martin (New York: Penguin Books, 1994); James Birket, Some Cursory Remarks by James Birket Made in His Voyage to North America, 1750-1751 (New Haven: Yale University Press, 1916).

One of the many travelers who passed through Weston along the Boston Post Road. The distance from Boston was a principal reason for the presence of so many taverns in this area. Washington returned in 1789 and spent the night a little further down the road, at the Flagg Tavern, which burned in 1902. Behind the plaque above is the newly restored Josiah Smith Tavern from 1757.

A stone marker on the grounds of the Josiah Smith Tavern commemorates a more famous Post Road traveler and is one of the reasons the Upper Boston Post Road is more famous than the Lower Boston Post Road. (Incidentally, I never encountered any markers commemorating the voyages of Hamilton, Knight, or Birket on the Lower Post Road!) George Washington traveled along the Upper Boston Post Road on two separate occasions. The first visit occurred in the spring of 1775 when General Washington passed through Weston on his way to take command of the newly formed Continental Army at Cambridge. Similar markers can also be found along the road in Waltham, Watertown, and Cambridge. The second visit, which occurred in 1789, when President Washington toured all the New England states that had recently ratified the Constitution, had a greater significance for the town of Weston because Washington actually slept in town the night before his arrival in Boston, just a little further along Boston Post Road.25As Rhode Island had not ratified the Constitution by the time of Washington’s New England tour, he avoided a visit there and returned to New York through Connecticut via the third and least well known Middle Post Road. He did eventually visit Rhode Island after the Constitution was ratified by the Legislature. Incidentally, Washington’s two trips were commemorated in every town along the route in Massachusetts by the dedication of the George Washington Memorial Highway in 1932, the bicentennial year of Washington’s birth. Plaques were put up in all the towns along Washington’s route, including Weston. I have previously passed plaques along the road in Cambridge, Watertown, and Waltham. The plaque in Weston was curiously removed for “safekeeping” in recent years from its spot near 626 Boston Post Road. See Fox, p. 146. Weston, much like Dedham along the Lower Post Road, was a convenient stopping point for travelers in the Colonial era, sufficient distance from Boston to make a good stop for refreshment if on horseback, a good day’s journey for someone on foot or traveling with wagons loaded with goods on roads of poor quality, especially in unpleasant weather. Unlike his first visit, Washington, though he traveled on horseback, was in no particular haste to reach his destination, and so his pace was more leisurely in 1789 compared with that of 1775, especially as he was feted in every town through which he passed. Hence the profusion of “Washington slept here” stories in numerous local histories.

Two men who traveled the same road and slept in Weston four months before Washington’s hasty 1775 journey to Cambridge were not celebrated by the townspeople they encountered en route; in fact, Captain William Browne of the 52nd Regiment and Ensign Henry DeBerniere of the 10th Regiment of His Majesty’s Army very nearly failed to escape with their lives as recorded in a report of their mission submitted to their commander, Military Governor of Massachusetts General Thomas Gage, which was found among the documents abandoned during the hasty evacuation of British forces from Boston in March 1776. This early victory of Washington’s Continental Army was aided by artillery captured after the successful siege of Fort Ticonderoga in May, 1775 and transported along this same road the following winter by Henry Knox and his soldiers, an event commemorated by another marker along the road here in Weston.

Golden Ball Tavern on a Spring day.

Browne and DeBerniere’s mission, much like the objective of this project, was to “take a sketch of the country”, to “mark out roads and distances from town to town, as also the situation and nature of the country”, to “notice the situation of the towns and villages…whether they are advantageous spots to take post in”.26All the quotes are taken directly from the narrative report submitted to Gage by the two men to which I have appended a link above. Their adventures can also be followed on the map of their travels; a detail of the Weston section of the map is reproduced above. I am starting to feel as if mine is also a spying mission! As discussed in previous entries, the two men set out from Boston, traveled through Cambridge, stopped at a tavern on the Waltham/Watertown border where they immediately aroused suspicion, continued on “and went about six miles further” through Waltham into Weston, where they met up with two men who “seemed very desirous to join company with us….As we began to suspect something we stopped at a tavern at the sign of the golden-ball”, a tavern that still exists in the center of Weston along Boston Post Road.

The detailed report of the two spies is of great interest to me as it provides a great deal of information about the Boston Post Road in 1775 and much of their story centers on their comings and goings from the Golden Ball Tavern. The building was completed in 1768 by Isaac Jones, a descendant of one of the original settlers of Weston. Jones was one of Weston’s wealthiest men as evidenced by his ownership of “the prestigious front row pew at the meetinghouse.”27Fox, p. 365. The “landlord” of the tavern, in the words of Thomas Anburey, a Lieutenant in the army of General Burgoyne, who passed through Weston in November 1777 as a prisoner of war following Burgoyne’s surrender at Saratoga, was also “a friend to our Government, and like all of that description, has been much persecuted. He was not without his apprehensions of being sent to prison for attentions shewn to the officers who stopped at his house, which was nothing more than the common civility he shewed to all his guests: in short, he was deemed by the Americans a rank Tory.”28Thomas Anburey, Travels Through the Interior Parts of America, Vol. II (Boston: Houghton Mifflin, 1923), p. 35.

Browne and DeBerniere similarly discovered “upon our going in the landlord pleased us so much, as he was not inquisitive, that we resolved to lye there that night.” Later, when proffered a drink, “he told us we might have what we pleased, either tea or coffee. We immediately found out with whom we were, and were not a little pleased to find, on some conversation, that he was a friend to government.” The two spies took Jones’ advice on the most useful route to their final destination of Worcester and the two men set off the next day on their ever more perilous journey west, heading to Worcester via Framingham along the Old Connecticut Path, an alternate route to Worcester which will be discussed in the next entry. After some hair-raising adventures Browne and DeBerniere returned to the Golden Ball five days later, on Tuesday February 28, where “on our arrival at Mr. Jones’s, we met with a very welcome reception, he being our friend.” The next morning they set off again, this time along the “Sudbury road, which was the main road that led to Worcester,” to survey an area they were unable to scout on the return trip from Worcester owing to an interaction with a suspicious horseman which caused them to deviate from their original plan. This last trip nearly proved fatal, and the two men were forced to do a round trip of “thirty two miles between two and half-after ten at night, through a road that every step we sunk to our ankles, and it blowing and drifting snow all the way.” Jones had been “sure we should meet with ill use in that country…but he said he found we were deaf to his hints.” Refreshed after “a bottle of mulled Madeira wine…we went to bed and slept as men could do, that were very much fatigued. The next morning, after breakfast, we set off for Boston.”

Golden Ball Tavern, June 12, 2022.

Browne and DeBerniere returned to the ‘wild west’ three weeks later, on March 20, this time to scout the area around Concord. They took a different route out of Boston and “came into the main road between the thirteen and fourteen milestones in the township of Weston…(and) took the Concord road.” It is difficult to interpret exactly what they mean in the description of their second trip. As I noted earlier, the distance from Boston to the meetinghouse in Weston would be more than 15 miles. Assuming Watertown Bridge was nine miles distant from Boston Town House, four miles further would be somewhere along Weston Street in Waltham, while a putative 14 mile stone would be located roughly at Summer Street, just past Dunkin Donuts. Even allowing for the possibility that the stone markers along the road measured the distance from Boston via the Charlestown ferry, the 0.8 miles saved still do not quite work: a 13 mile stone would be located on Sibley Road near the bridge over Stony Brook, while a 14 mile marker would be located at the west end of Crescent Street. Perhaps in their understandable haste they made a few mistakes; there are certainly numerous errors in the directions and distances of some of the roads along the route. On balance though, it is pretty impressive how accurate the map is considering the circumstances under which it was produced. They do not mention a visit to the Golden Ball on this second journey, perhaps not wanting to get Jones into any further trouble, or perhaps because it is past the entrance to Concord Road.

To me, the most astonishing aspect of this affair, is that Isaac Jones not only managed to keep his head, he kept his tavern, and he did not feel the need to escape to Boston or to abandon Massachusetts as so many Tories were obliged to do after March, 1776. Indeed, by 1777 Jones was aiding the Revolutionary Army and by 1778 was, according to the website of the Golden Ball Tavern Museum “serving on the Weston Committee to the Massachusetts Assembly that deliberated the merits of the proposed Massachusetts Constitution of 1778 (the first in the nation and a model for the US Constitution). Isaac and the committee opposed it because it did not extend voting rights to all people, ‘…which we esteem to be an infringement upon the Rights of such Subjects.’ The committee also objected ‘…because the said Constitution is not connected with a declaratory Bill of Rights, which we esteem to (be) the privilege of a free people,’ {24 May 1778, Committee of Weston to Massachusetts Assembly, Weston Town Archives}.” The tavern remained open until 1793, the house remained in the Jones family until 1963, and then became a museum that “was Weston’s 20th century preservation triumph.”29Fox, p. 365.

Tap room at the Golden Ball Tavern. The “bar” was built in 2009 for a film made by a Weston high school teacher, Ted Garland, about Isaac Jones called “Allegiance: The Legend of Isaac Jones”. An outline of the “cage” was found on the ceiling, and the design is authentic to the period.30Pamela Fox, personal correspondence.

On a lovely Sunday in June I take an illuminating tour of the museum led by a lovely tour guide named Doris. The house has been not been “restored” to a specific period, and there is evidence of many generations of the Jones family to be found in the various interesting rooms. Of course I am drawn to the Tap room at the front of the house and am rewarded with the sight of an eighteenth-century “cage bar”, an enclosure behind which alcohol was kept, the “bar closing” when the bars were literally pulled across the opening to lock it up for the night. Only it turns out to be a 2009 recreation of the original bar using an outline of the cage found on the ceiling, built for the production of a movie about Isaac Jones produced by a local high school teacher (see photo below). It is a testament to the skill of the modern carpenters who did a great job adhering to a design authentic to the period. However, I would be lying if I said I was not slightly disappointed to discover this fact.

Myth versus reality. Did I really expect a cage bar to survive intact for 250 years in a building that has been a family residence for all but a few decades of these last two plus centuries? Even if it survived that long period, what shape would it be in? Why is it disappointing to find that things are not exactly as they were in 1775? Shouldn’t it be enough that the building is still around, that it looks largely as it did in the eighteenth century and that there are local residents who take a deep pride in preserving what remains of their local heritage and are able to maintain it and indeed share it with the general public? The Jones residence could easily have been burned down in 1775 or at any point in the last two centuries. It could have been razed at any time and a large mansion or a shopping mall built on the foundation. Instead, it has persevered and retains vestiges of what it was in the 1770s along with what it was in the 1870s and even in the 1970s. That in itself makes it worth a visit. That is all I can hope for on my mythical adventure along this mythic road.


Once again, there is no @#$% sidewalk! After leaving the Golden Ball Tavern I head west for a quarter mile past charming nineteenth- and early twentieth-century houses with substantial, well-kept gardens along a shady, wide sidewalk. Then the “idyllic” section of Boston Post Road comes to an end as Route 20 curves slightly north and the busier road once again takes the Boston Post Road name at the junction with Highland Street for the last mile in Weston to the border with Wayland. The traffic is back, seemingly noisier than before, the minimal sidewalk is essentially unpaved as shown in a photo above. A walk along this road in February 2019 was almost impossible because of the accumulation of snow along the side of the road, allowing me to more deeply appreciate Browne and DeBerniere’s miserable trek along this same road 244 years earlier. Another more recent walk in the late spring along this road presented a different seasonal danger: much of the “sidewalk” is flanked and at times covered with poison ivy! Most of the land on either side of the road consisted of large tracts of farmland, some of which were developed in the twentieth century. Seemingly little of interest to be found along this stretch of the road. Oh well, not every mile can have something to offer.

But wait! 787 Boston Post Road looks like a nice old house. It turns out to be an “exceptionally fine late Georgian/Federal house built by John Flagg between 1774 and 1777, but then sold to Enoch Greenleaf, who was probably the first occupant.”31Fox, p. 392.This turns out to be a “red Flagg” for me as I am reminded that George Washington spent the night of October 23, 1789 in Weston at the Flagg Tavern, about which he wrote laconically “thence to Weston (14 more [miles] where we lodged)”.32Diary of George Washington, Friday October 23, 1789, p. 32. The building, which burned in 1902, stood at approximately 725 Boston Post Road, just west of Highland Street, and had some very colorful owners.33See Fox, p. 385. I backtrack a quarter of a mile to the site, of which there is little to see today, and then continue west on my somewhat purgatorial march into Wayland. I nearly miss another Colonial gem from c. 1750, called Hayfields, hidden behind a tall fence at 823 Boston Post Road “built for farmer Joseph Livermore.”34Fox, p. 392. Almost directly across the street is Weston Estates, a development dating to the 1960s that feels vaguely Californian and strangely out of place. Three minutes later I reach the border between Weston and Wayland. Only the two Colonial era houses plus a handful of interesting nineteenth-century buildings to show for the last mile. At this rate I will only have 100 or so more houses to write about by the time I get to Springfield. So much for my notion that this would be a “quiet” mile.

Just another Colonial gem along the “less interesting” section of the Boston Post Road in Weston. According to Pamela Fox this house, at 823 Boston Post Road near the border with Wayland, “was built for Joseph Livermore, a member of one of Weston’s early families. He reportedly operated a malt house on the property, which today includes a rare surviving ensemble of well-preserved outbuildings”35Fox, p. 392. Indeed, these are visible in the background.

Almost immediately upon entering Wayland, the road divides into two old roads. The left hand road is the “Old Connecticut Path”, about which I will have much more to say in the next entry. The road to the right is Boston Post Road, which continues along Route 20 for the next 1.5 miles. I am excited by the sight of the sign for Old Connecticut Path but dismayed by the prospect of more traffic along busy Boston Post Road. The highs and lows of walking the road inevitably will continue; a moment of elation at seeing an eighteenth-century house or a plaque commemorating the passage of George Washington, a desperate wish for more of the tranquil road, the “hearthside idea” of what the road should be like. Was it ever thus? Of course not, but the “artificial” town common of Weston is far preferable to standing by the Dunkin Donuts at the edge of Exit 41, Interstate 95. Stephen Jenkins, writing about Weston on his Post Road adventure waxed lyrical: “With the long evening light upon some of the swales filled with lush grasses, the pictures are beautiful in the extreme.”36Jenkins, p. 369. As I reflect on my walk across Weston along the route of the old Boston Post Road I find that, on balance, I am unable to disagree with his opinion.

We are always in the process of creating the past, the present, and the future; As we have seen, even the Boston Post Road is to some degree a reconstruction. Personally, a reconstruction of a past that may or may not have existed is preferable to the destruction that is the typical fate of most buildings, like the Flagg tavern, along the road and even of the landscape itself, as evidenced by the Exit 41 cloverleaf. I prefer myths, even if at times they can be noisy.

So in America when the sun goes down and I walk along the broken-down sidewalk and sense all that raw land that rolls in one unbelievable huge bulge over to the next town on the Boston Post Road and nobody knows what’s going to happen to anybody besides the forlorn rags of growing old, I think of Captain William Browne and of Ensign Henry DeBerniere, I think of Arthur Shurcliff, I think of Isaac Jones, and I think of Dean Moriarty…..

…..but I also think — I wish there was a #$*% sidewalk!



Pamela Fox deserves a special mention in this entry. I first met her on Weston town common one sunny May afternoon and had literally no idea at the time that she was the walking encyclopedia of all things Weston. For evidence, look no further than her impressive book Farm Town to Suburb: The History and Architecture of Weston, Massachusetts, 1830-2020. Second Edition, published by the Portsmouth, New Hampshire publishing house of Peter E. Randall (copies can be purchased from the Weston Historical Society). Along with photo editor Sarah Gilman, she has woven as rich a tapestry of a New England town as can be produced; if there is a topic not covered in this book (including COVID!), I would be surprised. For a visitor passing through towns along a road rich with history but often lacking in nuanced local historical perspectives, this book is a treasure trove of both detailed historical research and a critical analysis of key events in the history of Weston, written with a clear sense of pride in the town but not the starry-eyed boosterism and white-washing that is all too often the bane of local histories.

That Pamela Fox would be so helpful in assisting me in my own research, with thoughtful and useful replies to any query sent her way by a complete stranger with the audacity to write about a place I heretofore had never visited (Leo Martin Golf Course excepted) was an added bonus and a reflection of her generosity. Although everything I write in this essay is my responsibility, I cannot deny the influence of her book on the depth of detail I was able to bring to this essay, even if she and others might disagree with my analysis. Instead of the usual routine along the road where I discover something unusual and wonder about it until I get to the next town, this time I could just look for it in her book or even just ask. What a privilege.

Distance traveled in this entry: 3.3 miles.

Total Distance traveled along the road from the Old State House in Boston for this project: 17.4 miles.

Total Distance traveled along all the roads traveled for Boston Rambles: 57.3 miles

2 Responses to Weston, Massachusetts: The Myth of the Wild Weston

  1. […] the surrounding countryside, stopped at the Golden Ball Tavern along the Upper Boston Post Road in Weston on February 23, 1775. The intended destination of the two men, Ensign Henry DeBerniere and Captain […]


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