Southborough, Massachusetts: Lost Roads

Upper Boston Post Road #8 (UBPR#8) Alternate Route Entry #3

We then traveled through a very fine country, missed our way and went to Southborough; we were obliged to turn back a mile to get the right road.

Ensign Henry DeBerniere in his report to General Thomas Gage, Saturday, February 25, 1775.

Sometimes travelers get lost, sometimes the road gets lost. I have researched and walked old roads for almost two decades and one of the most frequent refrains I encounter regarding old roads is that they no longer exist, that they disappear into the woods, that they are lost in the mists of time. In almost every instance I have discovered that the road is alive and well. On occasion a section of the road has been rebuilt or has been widened or developed into a highway. Sometimes the road is exactly as it was and is merely difficult to envisage because of development alongside the road. The road is always there though, even if scarred and worn down over time.

Once in a while the old road has well and truly disappeared. In the town of Southborough, in not one but two cases, large sections of the “Old Road to Boston,” as it is called on Larkin Newton’s 1831 map of the town, have ceased to be, as the parrot owner once said. Two events in the history of this superficially somnolent rural town, the first town in Worcester County I have reached on this journey, markedly transformed both the topography of the town and erased large stretches of the old main road that led from Framingham to Worcester, a road along which a number of colonial-era notables, such as John Adams and the British spies Captain William Browne and Ensign Henry DeBerniere, traveled and recorded details of their journey.

The first event occurred in the eastern section of Southborough, when the Stony Brook branch of the Sudbury River was dammed, creating large reservoirs in the valley of the river and erasing more than a mile of the old main road east of the town center on the way to Framingham. The second event occurred nearly a century later in the western section of Southborough, when a two-mile stretch of Interstate 495 was pushed through the town in a north-south line from Westborough to Marlborough, effectively isolating a triangular-shaped piece of the town of Southborough on the Westborough side of the highway and abruptly terminating the old road, creating a 300 yard gap in the road which resumes on the western flank of I-495 and leads into Westborough. The original main road measured five miles in length from the border with Framingham to the border with Westborough. Close to 1.5 miles, about 30% of the entire road in Southborough of the “Old Road to Boston” no longer exists, and another mile of road, a half-mile each on both the eastern and western borders of Southborough is effectively isolated from the main part of the town and terminate abruptly. This will be a tricky town to navigate. I hope I don’t get lost like my predecessors.

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It is difficult to imagine that the quiet, narrow road I am following leading from Framingham into Southborough was ever an important transportation route. The principal road from Framingham to Worcester in the Colonial era continues along Waveney Road from Framingham over the border into Southborough just a few yards before it crosses Pine Hill Road. It then continues along Clemmons Street, a quiet road through the woods with a few older houses and one or two new houses going up in the woods, for a quarter mile. At this point the road ends at a gate blocking the path into the property surrounding the Sudbury Reservoir. I follow the path into the woods, which was once part of the original “Old Road to Boston,” but now is part of the Bay Circuit Trail, an “Outer Emerald Necklace” hiking trail more than 230 miles in length that starts in Newbury and circles the Boston metropolitan area, ultimately ending along the South Shore in Duxbury.¹To answer the question that I know has popped into your head, yes I have walked substantial parts of this hiking trail, particularly at the North and South shore ends and near Lincoln and Concord, but I have not walked the whole trail, yet. I continue along the eastern edge of the reservoir for another quarter mile, until I reach an unmarked spot where the road would have been submerged by the construction of the dam that flooded the area. The Sudbury Reservoir, which was created in 1897 by the building of the Sudbury Dam on the Framingham and Southborough line between 1894 and 1898, flooded an area of about two square miles, including almost 10% of the total land area of the town of Southborough. This reservoir, along with a series of dams along the Sudbury River in Hopkinton, Ashland, Framingham, and Natick, as well as along Stony Brook in Southborough, were all part of a large project to provide more water to the rapidly growing Boston metropolitan area in the late nineteenth century.

In the course of flooding the area, over 60 houses were moved and a large amount of farmland was lost. The main impact, in terms of the project I am currently writing about, was the loss of the old road along which Browne and DeBerniere, John Adams, the Reverend Ebeneezer Parkman, and many others traveled to and from Boston. In total, about 1.4 miles of the road in Southborough was lost either to the reservoir itself or as part of the property surrounding the reservoir, which the state controls under the auspices of the Massachusetts Water Resources Authority (MWRA). The route of the original road lost to the reservoir and surrounding property is shown on the map above.

After backtracking along the path along the eastern shore of the reservoir, I make my way around to the western shore and find the short stretch of trail in the woods that leads to the water’s edge and have a look across at the peninsula in the middle of the reservoir, along which presumably a large section of the original road lies hidden in the woods. This view is shown in the image at the beginning of this entry. Then I backtrack out of the woods, cross Framingham Road, and begin to walk along a part of the road that still exists.

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East Main Street in Southborough is a quiet residential street that gives little hint, but for the name, that it was an important road along which many travelers once passed. A few yards along the road as I head west away from the Sudbury Reservoir I come across a large hint, another in the long series of milestones I have encountered along the “Framingham Road” since I began walking this deviation from the Upper Boston Post Road in Wayland at the border with Weston. I encountered three stones in Wayland, a further four stones in Framingham (a fifth has gone missing), and now I reach milestone 28 in front of 34 Main Street, indicating that, despite appearances, this was indeed the Old Road to Boston. Incidentally, the distance along the original route of the “Old Road” to the 24-mile stone in Framingham is almost exactly four miles.

The creation of the reservoir was a sort of final blow to the old road to Boston, officially eliminating a piece of a road that had long lost its central role as the principal road through Southborough, a fact alluded to by Larkin Newton on his 1831 map, where he refers to this road as “the Old Road to Boston.” The opening of the Worcester Turnpike, a little more than a mile south of this road in 1810, was the major blow, but the coming of the railroad a few decades later, along with the rerouting of Boston Road (Route 30) around the southern end of the reservoir all changed the traffic patterns of Southborough such that that this short stretch of Main Street east of the junction with Main and Boston Road today seems as though it has been a perpetually tranquil back road, a fact belied by the presence of the milestone, an indication that this was once the main road to Boston for many travelers. It is clearly the “3 Rod County Road,” the principal road shown on the official map of Southborough published in 1795 by Nathan Bridges, crossing the Stony Brook twice before continuing into Framingham. Today the two crossing points are the shores of the reservoir, but East Main Street continues today in a direct line to the most recent version of the Meeting House that is a prominent feature of the map (see below).

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Not that Southborough is, or ever was, a bustling boom town like Boston or Worcester or even neighboring Framingham. The population struggled to stay at 2,000 inhabitants for most of its history, only crossing the 3,000 barrier sometime in the 1950s when, like many towns surrounding Boston, an exodus to the suburbs resulted in dramatic population increase in what had for over two centuries been mostly quiet rural towns or small villages with some modest manufacturing. Southborough’s population, although more than tripling in the last seventy years, only cracked the 10,000 resident mark in the 2020 census, despite the presence of the Worcester Turnpike (Route 9), the railroad (Southborough stop on the Worcester line on the southern edge of town near Hopkinton), the Massachusetts Turnpike (Interstate 90), and Interstate 495, the outer ring road of Boston. Situated nearly 30 miles outside Boston and 15 miles from Worcester, Southborough has managed for most of its history to escape the orbit of both, although that slowly seems to be changing as people move further and further from the hub in search of more affordable housing. Of course, as this entry about a lost road has shown, even before the recent influx of suburban housing development, the influence of the Hub impacted the very landscape of this distant town in a dramatic way, submerging vast sections of the eastern portion of town and carving a two-mile interstate wall, I mean highway, through the western end of town. Even the rural character of large sections of the town was heavily influenced by the tastes of wealthy Bostonians, as we shall shortly see.

Main Street, after the intersection with Boston Road (when Main Street becomes Route 30 through the rest of Southborough and into Westborough), is the historic center of Southborough and is a little more vibrant than the residential stretch along East Main Street, although it is still quite a bucolic New England town center, with little commercial development apart from the usual (invariably Greek) “house of pizza”, a diner, and a few small stores. The lack of commercial activity does not diminish my interest in the center as it contains many sights of historic interest, including a wide range of residential architecture spanning two centuries.

The main points of interest in the center of town are found near the intersection of Main Street (Route 30) and Marlborough Street (Route 85). Along Main Street just east of the intersection is another of the stone markers commemorating the journey made by Colonel Henry Knox and the teamsters who hauled dozens of artillery pieces from Fort Ticonderoga to Boston in the winter of 1775-1776. Although the route taken by Knox and his team is not known with certainty after they reached the Connecticut River in Springfield (Knox ceased making diary entries in Westfield after January 11, 1776), a putative route was established in the 1920s and markers were placed across the state in 1927. It was thought that Knox and his train of artillery traveled along the route of the Upper Boston Post Road from Springfield to Marlborough, then proceeded south from the center of Marlborough along Route 85 (Maple Streeet in Marlborough and Marlborough Street in Southborough) to the junction here in Southborough Center before proceeding east along the route I have been following (with the exception of the section now under water) through Southborough into Framingham, where the artillery was stored somewhere in the vicinity of Buckminster’s tavern (see the previous entry for more details). The reason Knox would have decided to detour south from Marlborough is unclear, especially as there were shorter routes to Boston either through Northborough and Westborough to this point and then on to Framingham as we shall see, or continuing through Marlborough to Sudbury along the Upper Boston Post Road.

Regardless of the actual route, the marker is the first indication of the historic importance of this junction in the history of Southborough. Directly across the street from the Knox marker, on the northeast corner of the intersection of Main and Marlborough Streets is a grassy area belonging to the St. Mark’s School, founded in 1865. The first building used for the new school was an old house that once stood on this corner, which was eventually knocked down as the school expanded. This house belonged to Timothy Brigham, one of the early English settlers of what became Southborough. His house, built about 1725, was used as the site of early church services before the area that is now Southborough separated from the town of Marlborough in 1727.

Timothy Brigham’s centrally located house also served as a “way station for travelers along the main road from Framingham in the east to Worcester in the west….it was ideal for waiting for repairs or for breaking a long journey.”²Richard E. Noble, Fences of Stone: A History of Southborough, Massachusetts, 1600-1990. Peter E. Randall publisher for the town of Southborough, p. 37. Reverend Ebeneezer Parkman, longtime minister of Westborough and assiduous diarist, records a stop there in April, 1736 when “Four of us Lodged at Ensign Timothy Brighams.” Parkman traveled regularly to Southborough and described a stop in November, 1737, another in October 1739, and another stop there in June 1754 on his way home from Boston; “In Southborough a storm rising (after I left Mr. Stones) I was oblig’d to stop at Lieutenant Brighams.” By 1759, when Parkman records another stop, Brigham had been promoted again: “I sat out upon my Journey. Called at Coll. Brighams to Congratulate him and his New Wife upon their late marriage.” John Adams lends further credence to the idea that the house was a stopping point for travelers, as he recorded a stop there on his way to Worcester in April, 1771, when he “Dined last Monday (April 22, 1771) at Brighams in Southborough, and lodged at Furnasses in Shrewsbury.”

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Directly across Marlborough Road, on a hill just past the library, is the focal point of historic Southborough, an area containing the old burying ground, the original house of worship, the town hall, and St. Marks episcopal church, forerunner of the school which is such a large presence in the town. The burying ground was originally used by the Nipmucs, an Algonkian-speaking people who lived in villages in central Massachusetts, but whose population had been decimated by diseases brought by European settlers.³Michael G. Johnson, Encyclopedia of Native Tribes of North America, 2nd Ed. Buffalo, NY: Firefly Books, 2014. p. 25. The early English settlers of what became Southborough continued to use the area as a burial ground, particularly as many of the remaining Nipmucs had converted to Christianity and the burial ground was thus considered consecrated ground.⁴Noble, Fences of Stone, p. 43. Here are the graves of the earliest settlers of the town, including Timothy Brigham and the first minister for the town of Southborough, Nathan Stone, who served as minister for the town for over 50 years, from 1730 until his death in 1781.

Reverend Stone arrived shortly after the construction of the first meeting house in 1728 immediately adjacent to the burial ground. The road I have been following was traveled in early October, 1728 by Dudley Woodbridge, a physician from Connecticut who kept a short diary of a trip from Cambridge to Western Massachusetts, mentioning meetinghouses and other prominent features along his route. Leaving Framingham Common on the morning of October 2, 1728, Woodbridge continued west “travelling about 5 miles in a way not so good we came to Southborough Meetinghouse on my right hand side.” The original building was a square two-story one room structure. This was replaced in 1806 by a church with a Revere bell in the steeple.⁵Noble, Fences of Stone, p. 110. The Unitarian/Trinitarian controversy that tore through virtually every congregation in New England resulted in the usual split, with the “Pilgrims” as the Orthodox Trinitarians were called, forming a new church a little east of the present site. Curiously, the Unitarians did not fare well despite their possession of the Meetinghouse, perhaps losing members to a revival of the nearly extinct Anglican faith in New England, perhaps unsurprisingly known in the United States as the Episcopal Church to distinguish it from the church of the country from which the states broke away. The decline of the Unitarians resulted in a deal to transfer ownership of the original meetinghouse to the Congregationalists (another name for the Orthodox, Trinitarian “Pilgrims”), and a renovated building was reestablished in 1858 as the Pilgrim Church of Christ Southborough.⁶Nobel, Fences of Stone, p. 160. This extremely well-preserved building still stands prominently today on the hill overlooking the crossroads at the center of Southborough.

A trio of interesting buildings sits atop the little hill that rises over the northwest corner of the junction at the center of Southborough. Immediately beyond the aforementioned lovely, iconic New England village church is Southborough Town Hall, “a handsome Italianate brick building with sandstone trim, a shallow mansard or double-hipped roof, and a triangular-pedimented center pavilion,” as reported in the Narrative History of Southborough (p.18), part of the Survey of Historic Properties conducted in 2000. To the west of the impressive Town Hall is the elegant St. Mark’s Episcopal Church of 1863, “an extremely well-preserved American imitation of a small stone English country Gothic church.”⁷Narrative History of Southborough, p. 18. Both St. Mark’s and Southborough Town Hall were designed by Framingham architect Alexander Esty, whose imaginative churches, libraries, and town halls brighten the landscape of many New England villages, towns, and cities. This trinity of institutional gems hidden away in this small town with a nondescript name nearly thirty miles distant from Boston reminds me why I enjoy walking along these old roads.

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The formidable presence of the Episcopal church and the nearby schools associated with it, can be traced to the influence of one man, Joseph Burnett. A native of Southborough, Burnett graduated as a Doctor of Chemistry from Worcester Technical College and the Worcester College of Pharmacy in 1837 at the age of 17. He then moved to Boston and earned his fortune first as an employee and ultimately as a partner in the apothecary of Theodore Metcalf (first located at 39 Tremont Street in Peter Faneuils’ old house). By 1855 Burnett had struck out on his own; his most well-known product being Cocoaine For the Hair, which despite the name, did not contain cocaine but rather Cocoanut Oil.⁸Apparently the name was made to sound like other popular products that did contain cocaine, an unsurprisingly popular ingredient in many “medicines” of the time

In 1850 the wealthy Burnett moved with his family back to Southborough into a newly built estate called Deerfoot Mansion, a building which still stands a little further along Main Street as we shall soon see. Burnett had met his wife at the Church of the Advent in Boston, and returned to Southborough as a practicing Episcopalian. However, Southborough’s churches in 1850 were confined to the Unitarians holding their services for a dwindling membership in the original meetinghouse, the “Pilgrims” who were soon to take over the aforementioned church building, and a Baptist church along the Worcester turnpike in the south of town. By 1853 Burnett had succeeded in establishing an Episcopal parish in Southborough, although it took a further ten years before the services ceased being held at Burnetts’s estate and St. Mark’s Episcopal Church was opened for services.⁹Noble, Fences of Stone, p. 156.

Burnett’s first son attended the Episcopal St. Paul’s School in Concord, New Hampshire, but Burnett was advised by Henry Augustus Coit, the head of the increasingly prestigious school that, since Burnett had five more sons, he might consider starting a new institution closer to home. Thus “St. Mark’s School in Southborough, Massachusetts, officially opened for business on September 13, 1865.”¹⁰Noble, Fences of Stone, p. 177. The Fay School, another school in the center of Southborough along Main Street, a preparatory school for St. Mark’s School, was opened the following year. Today the two campuses take up a significant amount of the center of Southborough, St. Mark’s to the north of the junction along the Marlborough Road and the Fay School along the south side of Main Street opposite “Holy Hill” and its imposing institutional buildings. Indeed, Burnett’s influence and wealth are visible all along the old road west from Southborough center towards Westborough. The Fay school, begun in a nineteenth-century mansion on Main Street, has expanded into a number of older residential structures along the road as well as adding more modern buildings. For nearly half a mile the various buildings and playing fields of the school are ever present as I walk along Main Street. Only when I reach Parkerville Road does the reach of the Fay School end as the impressive grounds of Deerfoot Mansion, designed by Frederick Law Olmstead, command the view. Burnett in later years turned his attention to farming, and the successful farm attracted a few other “gentleman” farmers to the area, creating a bucolic scene that even in the nineteenth century was regarded as something of a rural ideal.¹¹Narrative of Southborough, p. 22. The views along the old road west of Southborough center are frequently quite beautiful, a “very fine country” indeed, in the words of Ensign Henry DeBerniere, who traveled through the area in the winter of 1775.

Following the example of Burnett and Deerfoot Farm, other large farms were established in the area by wealthy Bostonians. On the north side of Main Street, across from Deerfoot farm, J. Montgomery Sears, reputed to be the richest man in Massachusetts, purchased a number of smaller farms to create Wolf Pen Farm on the north side of Main Street, a sprawling 400-acre country estate, with a Queen Anne mansion, currently being converted to condominiums, at the corner of Sears Road and Main Street. Of interest to this project is a milestone that sits at the corner on the former Sears property. This milestone, inscribed with the date 1769, is the 27-mile stone along this road. However, since we have already passed the 28-mile stone more than a mile back along the road, it is an obvious case where the milestone has been relocated. Since this milestone would have been located in the middle of the Sudbury Reservoir, it is likely that it was moved to save it from being submerged or lost in the flood.

Abutting Wolf Pen Farm to the west was yet another large estate run by a “gentleman farmer.” Chestnut Hill Farm was the estate of Sears’ father-in-law, prominent lawyer Charles F. Choate.¹²Narrative History of Southborough, p. 22. This impressive property maintains much of the look it once had thanks to the efforts of the Trustees of Reservations, who maintain much of the property as a working farm. I take an hour or two birding detour along the trails of this idyllic property (full confession: I traveled this road twice in the past four months, once in January and once in April, and detoured on both occasions for a birding diversion) before resuming the old road from Framingham to Worcester.

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Directly opposite Chestnut Hill Farm, just beyond Chestnut Hill Road, is Lynbrook Road, which veers southwest away from Main Street (Route 30) in Southborough. Prior to 1955 Lynbrook Road was Main Street, but the bifurcation of the area by the creation of Interstate 495 resulted in the construction of a new section of Main Street/Route 30 and the old road was bypassed. Since my interest is in the old road, I turn left and follow the “old” Main Street, today’s Lynbrook Road instead of the modern Main Street. Lynbrook Road is named for yet another of the large estates that graced this section of Southborough, Lynbrook Farm, acquired by Margaret Lindsay, grand-daughter of department store magnate Marshall Fields, and her husband Thomas Lindsay in 1906.¹³Narrative History of Southborough, p.22. Most of the scenery is still bucolic (see photo below), but recent developments have begun to mar the beauty of the area, especially as the architectural styles chosen by the developers of these large houses are, unsurprisingly, quite tasteless. Nevertheless, the road is fairly tranquil and there are enough rural vistas to satisfy my needs as I make my way along the old road to it’s inevitable termination.

In truth the roads in this area have been altered fairly frequently over the course of two centuries, as I discovered during a detailed examination of maps of the area dating back to 1794. A shorter route between Westborough and Southborough, today’s East Main Street in Westborough appears sometime after 1830 on maps of the area, bypassing the original route of the road to Worcester, which followed what is now Lynbrook Road to become Burnett Road on the other side of Route 495, which turned into Smith Street at the Westborough line. Prior to the construction of the Interstate, East Main Street curved northwest a little after Lover’s Lane in Southborough, continuing along the route of today’s Granuaile Road, rejoining Route 30 a little further just before the border with Westborough. A USGS map of the area in 1943 shows what was once the old road road as an unpaved trail leading to Smith Street at the Westborough line. Today the road abruptly stops as the imposing wall of Interstate 495 rises above the landscape.

Burnett Road, the continuation of the old road on the western side of the highway, is not particularly interesting; like its eastern counterpart on the border between Southborough and Framingham, it is difficult to picture this road ever having had any role of importance whatsoever. The road continues for about half a mile until reaching the border with Westborough. Overall, this stretch is a bit anticlimactic; there are wooded lots, a big new housing development, and some suburban ranch houses from the 1950s and 1960s and then I almost imperceptibly cross over into the town of Westborough. I expect the disappearance of the old road plus the construction of the highway turned a quiet corner of Southborough into an even more isolated quieter corner of Southborough. Just as the road at the beginning of this entry seemed insignificant and yet was the principal route between Framingham and Worcester so too this quiet insignificant track on the forlorn edge of Southborough once played a role in the lives of many travelers heading east or west in Massachusetts, a role now relegated to brief dispatches in the diaries of long-dead travelers and to the early maps of the towns of the newly-formed nation. Which road Browne and DeBerniere mistakenly took I have not figured out, but all is not lost, for I have at least rediscovered some of the lost road.

End of the road. The old road terminates here as Interstate 495 rises above the old road, which resumes on the opposite side of the highway as Burnett Road. Hard to believe there is a highway here but trust me, you can hear it clearly when you are standing at this spot.

Total distance traveled in this entry: 5.0 miles

Total distance covered on the Framingham Diversion Route: 15.6 miles

Total distance covered for all the walks described in Boston Rambles: 77.1 miles