Leicester, Massachusetts, #2.

Savoring the Fruits of Leicester

Part Two- A Walk Up Strawberry Hill

Upper Boston Post Road #21 (UBPR #21).

Milestone reading “54 Miles From Boston” located on Leicester Common. In the background is Leicester Unitarian Church (1834). The stone was placed here in 2016, close to its original location, after it wandered around town for several decades.

“Set out for Springfield with Mr. Davenport….eat Roast Turkey near Strawberry-Hill, I eat mine there at Sarah Stebbings’s.”

Samuel Sewall, Diary, Tuesday August 28, 1716.

“Geography has its excitements.”

Robert Byron, The Road to Oxiana, 1937.

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Introduction

The previous entry about my walk along the route of the Upper Boston Post Road through the town of Leicester, Massachusetts, focused on the various roads leading into Leicester from Worcester, and then followed the road through an area called Cherry Valley, which is part of the Blackstone River watershed area. The topography of the area and the development of Cherry Valley have much in common with the neighboring city of Worcester, giving the walk a transitional feel. As I climb the steep hill into the historic center of the town of Leicester, the second part of the walk already has a distinctly different feel from the first part of the walk and indeed feels quite different from most of the first 53 miles I have walked thus far along the route of the Upper Boston Post Road.

The first noticeable difference is the elevation. As I reach Leicester Common and the lovely assemblage of historic buildings that line the green expanse, the road passes the 1,000 feet above sea level mark, by far the highest point thus far along the road. Most of Leicester is in the French River watershed, which flows south, eventually feeding into the Thames River, which empties into Long Island Sound at New London, Connecticut. The northwestern corner of Leicester is part of the Quaboag River watershed, which feeds into the Connecticut River near Springfield. This elevated area is a sort of miniature “Continental Divide” on the route of the Upper Boston Post Road: east of this hill the water flows in an eastward direction- in most of Leicester the water flows in a southward direction- but by the time the road reaches the border with Spencer, the water flows west. The road follows the same route as the water through the valleys of Central Massachusetts to Springfield.

The road also changes in character along the way. The first 50 or so miles passed through towns that mostly look towards Boston and Worcester (which, however one feels about it, increasingly is becoming a bedroom community of Greater Boston). However, the towns along this section of the road are rural in character, despite the fact that more than a few, including Leicester, have a long history of manufacturing. The demographic and political character of the eleven towns between Worcester and Springfield are also quite different from the towns along the road in Greater Boston. All of the towns are less-densely populated than any town on the road from Boston to Worcester; the towns are typically more White, more conservative, and generally have lower per-capita income (PCI) levels than the relatively wealthy towns between Boston and Worcester.¹

Leicester is the first of the eleven towns along the road from Worcester to Springfield, and the second part of the walk through the town will start as the road enters Leicester Center, passing milestone 54 along the way. After examining the origins and development of the town in this entry, I will head west in the next entry for nearly three miles to the border with Spencer, by which time the transition from east-facing to west-facing will be complete, even if most of the residents along the way are still Red Sox fans.

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An (Infinitely?) Slow Climb.

*Grave of Peter Silvester (1755-1837) in Pine Grove Cemetery, Leicester. Silvester (or his father, 1713-1801) was the surveyor of the first official map of Leicester, produced in 1795.*

I begin my walk along the 54th mile of the route of the Upper Boston Post Road by crossing a small creek just west of Mannville Street and entering the French River watershed. The road then begins a long climb into Leicester Center. The elevation of the road at the creek is 833 feet above sea level. This turns out to be the lowest point along the route of the Upper Boston Post Road for the next 5.7 miles, including the remaining 3.4 miles of the road in Leicester and another 2.3 miles along the road in Spencer, from the border with Leicester all the way to Spencer Center. Just 200 yards ahead, at the junction of Main Street and Winslow Avenue, the road has already climbed to 860 feet in elevation. In the next half mile along the road, up what is now labelled “Leicester Hill” on USGS topographical maps but which has been called Meeting-house Hill or Strawberry Hill in the past, the elevation reaches a new height of 1013 feet at the current location of the “54 mile” stone in Washburn Square. Main Street climbs so steeply here that the electric trolleys of the Worcester and Suburban Electric Railway that once ran along Main Street from Worcester turned right and followed Winslow Avenue in order to gain elevation more slowly before turning south onto Paxton Street to regain Main Street on the west side of Washburn Square, as can be seen on an 1898 map of Leicester Center (Plate 24 of the 1898 Atlas of Worcester County, below).

A surprising number of the buildings shown on the 1898 map still exist. Enough buildings built before 1900 survive that all of Main Street, from Winslow Avenue/Henshaw Street in the east to the intersection of Main Street, Pleasant Street, and South Main Street (MA Route 9) on the west, is part of the Leicester Common/Washburn Square Historic District on the National Register of Historic Places (referred to as LEI.C on the Massachusetts Cultural Resource Information System, or MACRIS, as I will refer to it hereafter). Although most of the buildings date to the nineteenth century, a few buildings have links to the earliest settlement of Leicester in the first decades of the eighteenth century, as do records of the visits of travelers along the Upper Boston Post Road.

Leicester Village (or Leicester Center), which developed around Leicester Common (or Washburn Square), has been well documented by maps over the last two centuries. The earliest official map of the town was surveyed by Peter Silvester, Jr. in October, 1794 and officially completed on May 23, 1795. According to Emory Washburn, in his Historical Sketches of the Town of Leicester during the first Century from its Settlement (1860), Peter Silvester 2nd (1713-1801) “Lived for many years in a house on the eastern slope of Meeting-house Hill, where there is now a cellar, on the north side of the road.”² Peter Silvester 2nd (Jr.) also had a son named Peter (3rd, 1755-1837) who lived in the southwest part of town. It is likely that, although the map is signed “Peter Silvester, Jr.” the son (Peter 3rd) might have been the surveyor as he would have been forty years-old at the time and not eighty-one like his father. Regardless, Peter Silvester, Jr. (the elder Peter Silvester), who may or may not have been the surveyor of the 1795 map of Leicester, lived along the road as it heads uphill from Winslow Avenue.

*The Cole-Chilson House (1803), 882 Main Street, listed on the National Register of Historic Places, has seen better days.*

On an 1870 map of the area (see map below), Mrs. O.C. Sylvester, the widow of a man with the same surname as Peter Sylvester, is listed as the occupant of a house located directly opposite Henshaw Street (Winslow Avenue had not yet been built in 1870). The house at 882 Main Street, just west of Winslow Avenue, in a very poor state of repair and partially screened from view by an abundance of overgrown bushes and trees (see photo), is the easternmost property listed in the National Historic Register District Report (which, from now on, I will refer to as the Washburn Square Report). The house, referred to in the report as the Cole-Levi Chilson House (MACRIS record # LEI.104), was built in 1803 with an addition dating to 1823, and today it appears to be abandoned. On E.M. Woodford’s map of 1855, another excellent map of Leicester (also included below) the house is shown as occupied by “S. Forbes.” On the 1870 map it is the property of Mrs. O.C. Sylvester. Oliver C. Sylvester (1793-1870), a manufacturer, occupies a grave at Pine Grove Cemetery in Leicester and obviously had died by the time the map was produced. In 1898 the property was owned by E.C. McAuliffe, by which time Winslow Avenue, and the trolley line, had been pushed through the eastern half of the property. I have been unable to ascertain whether Oliver Silvester was related to Peter Silvester, or whether Peter Silvester had any connection to this particular property.

Amos Hill Coolidge, in his Brief History of Leicester (1890), states somewhat cryptically that, “at the foot of the hill, from 1823 to 1853, was the grocery of Evi Chilson, especially prized by students of the academy for the rare quality of its entertainment for the inner man.”³ The “Academy” refers to Leicester Academy, once located on Washburn Square/Leicester Common at the top of the hill, a building that is shown on Peter Silvester’s map of 1795. Apparently the name of the man who ran the grocery was Evi and not Levi as listed on the Washburn Square Report. The map of Leicester from 1831, like the 1795 map, does not have the detail of the later maps described above, so no houses are shown along this section of the road, although the fact that the road climbs a hill is indicated (see map later below in this entry). Thus, despite a thirty-year presence in the house at 882 Main Street, except for this brief reference in Coolidge’s book, Evi Chilson is a shadow.

An online search uncovers his gravestone in Pine Grove Cemetery (off Pine Street) in Leicester, not far from the grave of Oliver Sylvester. Evi Chilson lived from 1788 until 1853. Chilson’s wife, Catherine Moore, outlived him by 13 years (1795-1866) and is buried alongside him. Their two children, John (1824-1838) and George (1830-1855), both died young and are also buried in the family plot. As no Chilson is shown living at 882 Main Street on Woodford’s 1855 map, I wonder what became of Catherine Moore Chilson, whose husband and children predeceased her. Sadly, as much as I would like to keep looking into the story of 882 Main Street in Leicester, this is the sum total of the results of my investigation into the tenants of this first house along the road in the Washburn Square Report.

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Detail from 1898 Atlas of Worcester County, Plate 24, showing “Leicester Village.” Main Street is the route of the Upper Boston Post Road through Leicester Center. This very detailed map shows every structure along the route for over a mile, from the beginning of this walk at Mannville Street in the east, to just beyond Rawson Street on the west. Feel free to click on the map to open it in a new window and examine it in more detail as I discuss individual houses and sights along the road.

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This first house along the road is also an illustration of the possibilities as well as the perils presented as I try to walk along the Upper Boston Post Road and discover its history. It is tempting to follow the fate of every family in every house along the road, but of course if I adopted that approach I would still be rooted to the spot at the first step along the road and would never have moved. Striking a balance between learning as much as possible about the history of the buildings and the people along the road (and conveying a version of that information to the reader) and zipping down the road as quickly as possible to my final destination while painting broad brushstrokes of the scenery is the most difficult aspect of this project. I am reminded of a riddle I encountered as a young boy called the coastline paradox. I have always liked studying maps, and, in an essay about geography I read years ago, a question was presented about the length of the coast of Britain. The main point was that the length of the coastline depended on how precisely one decided to measure: it was theoretically possible to make the coastline almost infinitely long if one measured every single curve of every cliff. The point is that the history of the road could be made almost infinitely long if every single story associated with every house or curve along the road was followed to its ultimate conclusion. In order to make progress, by definition I have no choice but to gloss over swathes of rich and detailed history as I make my way west.

George Washington was one person we do know passed who along this road. He did so on July 1, 1775, as inscribed on this marker located along Main Street on Leicester Common, at the top of what was once called Strawberry Hill.

Another problem I encounter along the road is the often frustrating lack of information about many important aspects of it. For example, although the families of many Leicester residents are discussed, often in great detail, in both Washburn’s long (467 pages) book and in Coolidge’s relatively concise (122 pages) history of Leicester, many of the names of the residents of the houses shown on the maps in this entry are mentioned briefly, like Evi Chilson, or are not mentioned at all and so, unless they appear in the genealogical research of a descendant or appear in a fortuitous mention in a specific source, the names of the owners shown on the old maps are a testament to how much history has been lost. The above books on the history of Leicester, detailed as they are, ultimately are superficial attempts to capture the totality of the much deeper history of this or any town. As I peruse the old books and maps and record the names of the various inhabitants shown on the map, I revel when discovering a new detail pertinent to the history of the road, but also lament how much I do not know and how much is unknowable about its history.

The problem becomes appreciably more difficult as I try to uncover evidence for the road that predates the arrival of European settlers. The oldest sources at my disposal are, at best, three centuries old, and most of the documented evidence about the road is sparse even for these last three centuries. This is particularly true for the eighteenth century, although there are at least a few diaries that provide information about life along the road, as we shall see shortly. Evidence for and documents about the road prior to the eighteenth century are almost nonexistent. Although it is acknowledged that early settlers followed preexisting trails on their travels through New England, descriptions of these early routes are scarce and even those few extant narratives are unreliable.

As I wander along the road my mind often wanders as well, and I have a recurring fantasy that I acquire the ability to walk the road in the eighteenth century for a short while, in order to discover how close my project gets to describing what the road actually looked like at the time. Occasionally I fantasize about walking along the road in the seventeenth century or earlier, when the people who traveled these roads before Europeans showed up followed what was more likely a well-worn path through the woods between settlements of Nipmuc and other Algonkian-speaking people. And yet, despite the paucity of physical evidence of the people who lived along the road before the arrival of Europeans, which is sadly as scarce as evidence of the road before the eighteenth century, as I walk along the winding old road whose contours are so clearly shaped by the countless practical decisions made over the centuries by people who walked the route out of necessity, I nevertheless feel their presence.

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Detail from an 1870 Atlas of Worcester County by F.W. Beers showing Main Street through Leicester Center, from Henshaw Street in the east (right) to Rawson Street in the west (left). many of the houses shown on this map still exist and many are mentioned in this article. The first house mentioned is the house of “Mrs. O.C. Sylvester” which can be seen on the north side of Main Street just across from Henshaw Street on the right side of the map. This is the house in the photograph above.

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We Shall Be As A House Upon A Hill

The preceding ten paragraphs cover a distance along the road of about 200 yards, a clear illustration of the pitfalls of discussing every detail of the artifacts I encounter along the road. With apologies to those who might find my walk superficial in its coverage of the history of each town through which it passes, I do need to move at a slightly faster pace if I hope to finish this project! Although almost every house along the road up the hill is part of the Washburn Square Report, some are of more interest than others, particularly in regard to this project.

For instance the house across the street, a 1920s-1930s Arts and Crafts/Colonial Revival house at 879 Main Street (LEI.106), is interesting in the context of the architectural development of houses in the historic district, but it has no particular relevance to this project except that it is physically on the road. The same could be said for thousands of other houses I have encountered and will pass along the rest of the route. The house at 883 Main Street, called the Flint-Taylor House in the Washburn Square Report (LEI.105), was built in 1826 and moved here from a location near the square circa 1898, and was radically altered in the twentieth century, although a little of the original detail is still visible (the fanlight above the door, to give one example). The house at 886 Main Street, the Sanford Woodcock house (c.1829, with 19th century additions, LEI.103), is more interesting, but still not particularly relevant to this project. I struggle to understand why the next couple of houses (LEI.101, LEI.102), which were clearly built in the postwar period, are included in the Washburn Square Report at all. The lovely Greek Revival house at 918 Main Street, the Fitch-Whittemore House (1837, LEI.99), on the other hand, is worth a stop to appreciate its excellent state of preservation.

Reverend Samuel May, Jr. House (1834), 960 Main Street, Leicester, Massachusetts. The stone marker in front of the house is engraved “First House in Leicester on this lot in 1713.” This was the house built on the lot of John Stebbins discussed in the entry.

It is not until I am within sight of Washburn Square that I encounter properties with direct connections to the development and history of the Upper Boston Post Road. The first of these is the house high above the road at 960 Main Street. The Reverend Samuel J. May, Jr. house (1834, LEI.92, see photo) is not only an interesting house in its own right, but the property on which it sits is the site of one of the earliest houses built in the town of Leicester. The May house itself is of architectural interest, best summarized in the Washburn Square Report: “The Samuel May house retains the Federal-period, five-bay, hip-roofed form, but displays Greek Revival-style trim. Set well back from the street and sited on a grassy bank that descends to Main Street, the house has a commanding presence. Built in 1834, it rises 2½ stories, has a wood frame sheathed in clapboards, and is square in plan with a large, two-story ell. Two tall chimneys rise through the east and west slopes of the roof. Greek Revival-style details include a frieze at the eaves; a one-story porch, which surrounds three sides of the main body of the house; windows with block-cornered frames, and a large door frame with Greek tracery, a faceted block at the center of the lintel, and long sidelights and transom. A dormer on the facade was added in the early 20th century. The main entry is reached by a series of terraces; each with a set of stone steps in the expansive lawn.”

The house was built in 1834 after May arrived in Leicester to become the first minister of the newly-formed Unitarian Church. The newly-formed congregation built a new Greek Revival style church (5 Washburn Square: LEI.113) which still stands, a few minutes walk up the hill from the house, on the north side of Washburn Square, in which May was ordained on August 13, 1834, the evening after the dedication of the church. A native Bostonian and Harvard graduate, Samuel May, Jr. (1810-1899) trained for a year under the tutelage of his more famous namesake, the noted abolitionist and uncle of Louisa May Alcott, in a church in Brooklyn, Connecticut, then attended Harvard Divinity School before arriving in Leicester to take on his new assignment. May maintained his position as Unitarian minister in Leicester for twelve years and, according to Amos Hill Coolidge, had a mostly positive relationship with his congregation: “entire harmony of feeling existed between them, except with regard to one question, viz: that of slavery in the United States, and whether a Christian minister should or should not take part in the effort to bring that condition of slavery to an end. Mr. May regarding it his duty to take such part, and to seek to induce his hearers to do the same, several persons were so much dissatisfied as to withdraw themselves from the society. One or more others who remained being similarly dissatisfied, Mr. May decided to resign his office rather than be a cause of division, and the connection was closed in the summer of 1846.”⁴

After his departure as minister, May became an even more strident advocate for abolition, acting as the General Agent of the Massachusetts Anti-Slavery Society. May worked closely with William Lloyd Garrison, helped to organize hundreds of regular meetings and conventions for the Society, including Lucy Stone’s early anti-slavery lectures,⁵and, according to the website of the Boston African American National Historic Site, May also “joined the third and final iteration of the Boston Vigilance Committee. He worked with fellow abolitionists to protect those who came to and through Boston on the Underground Railroad. May became one of the Committee’s more active members—Francis Jackson’s account book documents twenty-seven separate instances of his aid to freedom seekers between 1850 and 1861.”⁶ Although it had long been suggested that the house in Leicester, which was built for May and his wife by his father as a wedding gift, was used as a stop on the Underground Railroad,⁷recent additional documentation in the Washburn Square Report (added in October 2024) states explicitly that “research undertaken after the listing of this district indicates that the Rev. Samuel May, Jr. House, 960 Main Street (LEI.92), a contributing property in the district, was not a stop on the Underground Railroad as stated in Section 8, p. 8 and p. 1 of the Bibliography. While Rev. May was involved in abolitionist activities, he undertook this work in Boston.”⁸

May, despite working in Boston for years, maintained the residence in Leicester until his death in 1899. Although the website for the Boston African American National Historic Site states that he was buried in the May family plot at Forest Hills Cemetery in Jamaica Plain, there is a gravestone in Pine Grove Cemetery for Rev. Samuel May and his wife Sarah (who predeceased him by four years), as well as memorials for his children. An obituary about Samuel May, published in 1899, said this regarding May’s house: “If it were possible to have an unembellished record of the Leicester home, it would present a truer picture of the struggle for emancipation than will ever find place upon the page of history…The cultured and the unlettered, the philanthropist and the [B]lack fugitive received equal welcome from him.”⁹ Even if fugitives were not hidden there, the spirit of the article is sound, as May himself assisted fugitives, albeit not at 960 Main Street in Leicester.

May remained engaged in civic life in Leicester for decades after relinquishing his role as minister, serving as director of the Leicester Public Library in 1861, as a trustee of Leicester Academy, and as a member of the State Legislature in 1874. May was also a committed pacifist, a leader in the Temperance Movement, and a supporter of women’s rights. According to the website for the Worcester Women’s History Project “Sarah and Samuel May, Jr. both attended that first National Woman’s Rights Convention held in Worcester, MA (in 1850). He served on the Business Committee and she became active in the School Suffrage Association along with her anti-slavery work.” So committed was May to the cause of abolition that, according to Amos Hill Coolidge, minister of the Congregational Church in Leicester and neighbor of the former Unitarian minister, that “from 1841 to 1865 Mr. May refused to take any political action under the United States Constitution because of its recognition and support of slavery; refused, that is, to vote for officers who must take an oath to support the Constitution. When the Constitution was amended he resumed the exercise of the citizen’s duties.”¹⁰ Samuel May clearly practiced what John Winthrop preached when he said “we shall be as a city upon a hill, the eyes of all people are upon us.”

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Detail from a map of Leicester produced in 1831 by an unknown author. This section of the map shows the route of the Upper Boston Post Road through the town, although here it is called the “Boston & Albany Post Road,” as the main road from Boston to Hartford and New York had been diverted along the Stafford Turnpike from Worcester by 1806 *(see upside down writing at center left of the map)*. However, this was the main east-west road through Massachusetts as early as the seventeenth century and very likely even earlier. Leicester Common is the prominent feature along the road, located in the center of the map at the summit of what was originally called “Strawberry Hill,” the outline of which is clearly visible on the map.

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Talking Turkey

As interesting as the story of Rev. Samuel May, Jr. and the house at 960 Main Street is, the property on which the house sits has an even more interesting history with a direct connection to the Boston Post Road. Leicester began to be permanently settled after 1713. In June, 1714, according to Amos Hill Coolidge, “fifty house-lots, of from thirty to fifty acres each were laid out, and sold for one shilling an acre… the lots were numbered, and the purchasers drew for choice. The first choice was drawn by John Stebbins. He chose the lot on Strawberry Hill, on which the house of Rev. Samuel May now stands. Here the first house in town was probably built.”¹¹ Not all the lots sold were taken up by the purchasers, but Emory Washburn states that “among the families we find here in 1717 are…Samuel Stebbins, the father of John and Joseph, who came here with him from England.”¹²

Samuel Sewall, Justice of the Massachusetts Superior Court of Judicature (now the Supreme Judicial Court) from 1693 to his death in 1730, kept a journal for more than fifty years which included details of his travels to oversee courts in various parts of Massachusetts. As early as August, 1698 Sewall passed through Leicester along the Upper Boston Post Road but states only that “Between Worcester and Quaboag we were greatly wet with rain; wet to the skin. Got thither before twas dark.”¹³ Quaboag is now Brookfield and so, traveling as he did in the rain, likely indicates that Leicester had not yet been settled or he might have paused for relief along the way. Nor is Leicester mentioned on the return trip a week later, on August 26, 1698, when Sewall again left Quaboag and summarized his trip succinctly: “to Marlborow.”¹⁴

Eighteen years later, on Monday, August 27, 1716, Sewall again headed west, and recorded in his diary that day, “set out for Springfield with Mr. Davenport.”¹⁵ After spending the first night in Marlborough, the group stopped in Worcester and then proceeded to Quaboag (called Brookfield by 1716) as previously. This time, however, the group stopped to “eat Roast Turkey near Strawberry-Hill, I eat mine there at Sarah Stebbings’s. Got to Brookfield a little after sunset.”¹⁶ From Springfield, Sewall followed a circuit through Connecticut and Rhode Island to oversee the court in Bristol County at Rehoboth (now Seekonk) before returning to Boston along the route of the Lower Boston Post Road and so did not return along the Upper Boston Post Road. Sewall did return to Springfield in 1718 following the same circuit as in 1716 but in reverse (Sewall started in Bristol County and finished his work in Springfield on this occasion), and once again recorded a stop, this time specifically mentioning the new name of the town: “September 24, 1718. Dine at Strawberry Hill, Leicester; Stebbing. Mr. Attorney Treated us. Visited Mr. Southgate.”¹⁷ He then proceeded to Worcester and on to Boston.

Although John Stebbins (sometimes spelled Stebbings) acquired Lot #1, according to James Draper, in his History of Spencer, Massachusetts (1860), “he and his brother were neither of them twenty-one years of age when they came to Leicester,”¹⁸ which implies that the “Sarah Stebbings” Sewall mentions is likely the wife of Samuel Stebbins and the mother of John and Joseph Stebbins. John Stebbins did marry Sarah Southgate, but this was in 1732, long after Sewall passed through. John Stebbins and his wife moved in 1737 to the part of Leicester that became Spencer, where we will visit them again. There is evidence that Samuel Stebbins’s wife was named Sarah on some genealogy websites, but the data provided for Samuel Stebbins is suspect (he is listed as being from Northampton, Massachusetts, but Washburn and Draper explicitly state that the family came from England), so I am uncertain if the Sarah Stebbins that Sewall refers to is the same person. However, since there were very few families in Leicester in 1716, it stands to reason that Sewall stopped at the property of the Stebbins family on the summit of “Strawberry Hill.” The diary entries of Samuel Sewall are the earliest documentation I have describing travel along the Upper Boston Post Road in Leicester.

Washburn traces the lineage of inhabitants of “the house (that) was, I presume, as old as any in town, if not the oldest and was probably erected by Mr. Samuel Stebbings, to whom lot No. 1-on which it stood- was allotted in the first division of the town. It was afterwards owned by Mr. Larkin, from whom it passed to Mr. Roberts, and from him to Mr. Conklin. Ebeneezer Adams, Esq. next owned the house; he moved into it in 1800, and thoroughly repaired it. Mr. Luther Wilson purchased the place of Mr. Adams. Mr. Alpheus Smith owned it and lived there many years after Mr. Wilson’s removal, and enlarged and repaired it and, at last, the house was removed by the Rev. May, Jr. to make room for his present much more elegant mansion.”¹⁹ Samuel May, a man with otherwise unimpeachable sound opinions, apparently did not realize the historical value of the building he had acquired and had it removed. As we have seen on many occasions already, preserving the artifacts along the Upper Boston Post Road has always been an uphill battle.

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A Common Walk

The Sprague-Flint-Denny House (1812) at 981 Main Street, Leicester. This Federal Period house is one of many older houses that line Washburn Square in Leicester. Notice the frayed blue Becker College banner above the porch. Becker College, which closed in 2021, once owned many of the stately buildings that comprise the Washburn Square Historic District. Many remain unoccupied as I write this entry in November 2025. Images of many of the houses along the south side of Main Street appear sporadically throughout this entry.

After walking west uphill a few yards past the May house I pass the entrance to Leicester High School and reach 1,000 foot elevation above sea level along the Upper Boston Post Road for the first time. From my new vantage point I can finally see the green of Leicester Common, also called Washburn Square, and the towers of the churches facing the Common on the north side of the square. Emory Washburn, using town records to describe the small village of Leicester as it was in 1767, states that “the only house between the Meeting-house and the Meeting-house Hill was one at its top, built by Mr. Stebbins, and afterwards owned by Mr. Conklin.”²⁰ Many more houses were subsequently built along Main Street, which runs along the southern edge of Leicester Common, and quite a few of the older ones survive and are part of the Washburn Square Report.

One of these houses sits across the street and slightly uphill from the May House at 963 Main Street. The charming Nelson-Russell House (LEI.91) was built in 1828 for John Nelson (1786-1871), minister for close to sixty years of the Congregational Church located across Washburn Square.²¹ Washburn Square itself was formally laid out around the same time after a century of existence as an undeveloped and ill-defined common. A few yards further along I reach the southeast corner of Washburn Square, where a succession of interesting buildings line the south side of Main Street facing Washburn Square, all of which are described in the Washburn Square Report. Rather than follow along Main Street and describe every building, as I make a circuit of the square I will discuss individual buildings as they connect to the narrative.

Washburn Square is an impressive site, conveying what the Washburn Square Report calls “a quiet and somewhat timeless quality. Traffic intrusion is minimized because this section of Main Street was bypassed by the construction of South Main Street as Route 9 in 1931.”²² The south side of the park-like square is lined with a series of houses in a variety of architectural styles mostly dating to the nineteenth century. Across Main Street, the route of the Upper Boston Post Road, the town green is slightly elevated above the street and is lined with impressive trees and a few markers to which I shall return. The north side of the square is “purposelessly treeless to accentuate the importance of the civic and institutional buildings that stand there (the First Congregational Church, Leicester Town Hall, and the Unitarian Church).”²³ Washburn Square also sits at the highest elevation in the area providing views in all directions, a bonus as I pass through on a sunny October day when the leaves have begun to turn color.

The square feels like the Hollywood set of the quintessential New England town common. There is also a strangely somnolent quality to the square, accentuated by fact that many of the buildings appear to be unoccupied and were adorned with the frayed blue flags of Becker College on my first visit. It turns out that Becker College closed in the aftermath of the pandemic at the end of the 2020-2021 Academic year, and much of the property was turned over to the town of Leicester. Becker College once operated two campuses; the first campus was opened in 1887, in the Elm Park neighborhood of Worcester, next door to Worcester Polytechnic Institute (WPI). As a student I once lived in an apartment right next door to one of the Becker College buildings, almost all of which have now been taken over by WPI, as I discovered on a recent visit to my old stomping ground. The second campus was here in Washburn Square, where Becker entered into a partnership with Leicester Junior College, which had taken over much of the property of Leicester Academy after its closure in the early twentieth-century. In 1977 the two colleges merged to become one college with two campuses seven miles apart from each other along the Upper Boston Post Road.

Becker College and its former partner Leicester Jr. College built a few new buildings, including the Swan Library (1962, LEI.108) on the southeast corner of Washburn Square, and occupied many of the other buildings around the square, including the Rev. Samuel May, Jr. House and the Nelson-Russell House, both of which appear currently to be unoccupied. The absence of students, and people in general, is keenly felt as I wander around the square, with Town Hall providing the only source of human activity in what feels a bit like an abandoned movie set.

That it wasn’t always this tranquil in Washburn Square is clear from the numerous stately houses lining the square, from the churches, and from the historical records, which describe not only the presence for more than a century of the well-known Leicester Academy on the northeast corner of the square, but also a thriving tavern dating to the earliest days of settlement on the west side of the square, a hotel that operated for more than a century on the south side of the square, and a surprisingly vigorous industrial scene in the nineteenth century all around the square and along many of the streets leading away from the center of Leicester.

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Church and State

*This marker was placed on the southwest corner of Leicester Common in 1904 by the Henshaw Chapter of the Daughters of the American Revolution.*

The center of town life in Leicester, as in every town in New England, revolved around the meeting house. As Emory Washburn eloquently phrased the undocumented origins of the first church in his History of Leicester: “From the known custom, however, which so generally prevailed in settling and incorporating of towns in Massachusetts in that general period, we may safely assume that a church was organized as early, at least, as the town itself. Every town, in fact, constituted a parish, though it managed its parochial affairs by means of its municipal organization; so that, as soon as a church had been gathered agreeably to the usages of the early-New England churches, the town was ready to call and settle a minister, if of ability to afford him the necessary support.”²⁴

The first meeting house was located on what is now the southwest corner of Leicester Common, on the north side of the Upper Boston Post Road (see photo of marker at left). This “small and plain rude structure” was erected in 1719 and served, with occasional additions and repairs, as the sole meeting house until 1784, when the second meeting house was built just behind the original building. This second building was moved to the site of the current Leicester First Congregational Church in 1828, on the site of Leicester’s first burial ground.²⁵ A third building replaced the second meeting house in 1867, but was destroyed by fire in 1899. The current building (LEI.115), designed by noted Leicester-born architect Stephen Earle, was erected in 1901. Earle was one of the most prominent architects of central Massachusetts and designed many of the cultural, educational, and religious buildings in Worcester, including the Worcester Art Museum, Boynton Hall at WPI, and many of the churches I discussed in previous entries.

In most towns, the meeting house would have been the only religious building in town in the eighteenth century and would also have served as the site of the town meeting. All the members of town paid a tax to maintain the building and to fund the minister. Leicester is a curious exception because some of the early settlers belonged to different religious organizations, a rarity in most of the towns through which the road has heretofore passed, but less unusual the further one gets from the seat of power in Boston. As early as 1732 a group, led by Ralph Earle, “declared themselves to the clerk of the town to be Friends and asked, on account of conscientious scruples, to be released from paying ‘any part of the tax for the seport [sic] of the minister or ministers established by the laws of the Province.'”²⁶ In 1739 the Friends, also known as Quakers, built their own meeting house north of the town center. A second meeting house was built in 1791 and lasted into the nineteenth century, when the congregation slowly declined and the building was removed. The “Quaker meetinghouse” appears on Peter Silvester’s 1795 map north of the town center. The Friends Cemetery, near the site of the former meeting house, makes a truly interesting pilgrimage, located as it is two miles north of Leicester Center along Mannville Street, on a quiet trail through the woods. Stephen Earle, the architect of Leicester First Congregational Church, was a direct descendant of Ralph Earle, and is buried in the Friends Cemetery. His father, Amos Earle, and other Earle family members played a significant role in the development of manufacturing as we shall see.

A second group of settlers adhered to the Baptist faith and established a church in the south of town, in what is now Greenville. Led by their first pastor, Dr. Thomas Green, the Baptists established a parish in Leicester by 1738 and a church by 1747.²⁷ Thomas Green (1699-1773) was also a prominent physician, mentioned on numerous occasions in the diary of Ebeneezer Parkman, the minister from Westborough whose descriptions of travel along the roads of Massachusetts I have consulted frequently in these entries. Green was also involved in a case in 1769 in the Worcester Inferior Court (Green vs Washburn) pitting his church against the town of Leicester over the thorny issue of taxation in which John Adams was involved. Coincidentally, Adams traveled along the Upper Boston Post Road in Green’s company two years later: “Rode this day from Worcester to Munns (in Sudbury) in Company with one Green of Leicester, who was very social, and good Company, an honest, clever Man.” The “Baptist meetinghouse” is also shown on Peter Silvester’s 1795 map, about three miles south of the “Congregational meetinghouse.”

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*View west along the north side of Washburn Square. From right to left are the Leicester Unitarian Church, Leicester Town Hall, and Leicester First Congregational Church.*

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The fact that for nearly a century there already had been more than one church in town likely made the inevitable split of the Congregational Church into two factions, a traumatic event which occurred in virtually every town along the route of the Upper Boston Post Route and in towns all over New England in the early decades of the nineteenth century, less fractious than the split in other towns. In 1833 a “Second Congregational Society” was formed. As we have seen, a new building was erected on Leicester Common, and Reverend Samuel May, Jr. was invited to become the first minister of the new church. The church erected at the time still stands (LEI.113, see photo above), although the steeple was replaced around 1901. Relations with the nearby First Congregational Church in Leicester apparently have been quite cordial over the years; not only have the two congregations hosted each other when one of the churches was unavailable but also, according to the website of the Leicester Unitarian Church, “Joint services were again held beginning November 1926 and on May 1st, 1927, they united as the Leicester Federated Church due to economic reasons. In 1927, the Second Congregational Church was incorporated as the Leicester Unitarian Church to establish two independent churches to unite through membership in a third entity known as the Leicester Federated Church.” However, the bond apparently has been uneasy as “In September of 2007, the Leicester Unitarian Church consisting of 12 members, dissolved the relationship with the First Congregation Church and hold(s) services year round in the Unitarian building that so proudly graces the Town Common. The result is a rediscovery of our Unitarian spirituality.” As I write, two “Puritan” congregations still worship on Washburn Square: the “Congregationalists” in the building immediately west of town hall, and the “Unitarians” in the building immediately east of town hall.

The division of the principal church in town into two separate congregations hastened the impending separation of church and state that had been brewing for decades. Taxes were no longer required to provide for the minister of the Congregation and, as the town was also rapidly growing, town meetings became increasingly uncomfortable to hold in the building housing what was renamed in 1833 the First Parish Congregational of Leicester.²⁸ The first Town Hall in Leicester was built next door in 1826. A newer building was put up in 1855 and the present Town Hall (LEI.114), in the same location between the Unitarian and the Congregational Church buildings on the north side of Washburn Square, was built in 1939. The civic and ecclesiastic buildings that line the north side of Washburn Square present as concise an image of the evolution of towns in New England as one will find.

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Back to School

On each of the maps of Leicester Center presented above, a fourth building is also prominently featured along the north side of the Common, at the northeast corner of Washburn Square. This building housed Leicester Academy, chartered in 1784 by an act of the Massachusetts General Court. This private academy was established as there was no school in Worcester County at the time providing for classical and English education.²⁹ Timothy Dwight (1752-1817), Congregagionalist minister and President of Yale, who traveled through New England and kept a record of his travels which was published posthumously in 1820-1821, wrote about the “neat village on the road, near the church, containing a respectable Academy. By an Academy as the term is used in New-England, and generally throughout the United States, is intended a school, between a parochial school, and a College, and approximating indefinitely towards either. In such a school are usually taught the English, Latin, Greek, and sometimes the French, languages; reading, with propriety, writing, speaking, composition, various branches of Mathematical science, and sometimes Logic, and Natural Philosophy. No system has, however, been formed, hitherto, for the regulation of Academies. A large proportion of those, who are destined to a liberal education, are here prepared for their admission into Colleges. At the same time, multitudes, who never receive such an education, are furnished with the knowledge, which qualifies them to enter upon various kinds of useful business.”³⁰

Leicester Academy attracted students from all over the county, and illustrious graduates included Emory Washburn, Oliver Ames, and John Davis, all Governors of Massachusetts in the nineteenth century. Incidentally Washburn Square is named for Emory Washburn.³¹ Massachusetts law eventually required the establishment of a free school in each town in the Commonwealth, and so, for a few decades, part of the school was used for the tuition of public school students. In 1917 a law was passed forbidding the use of public funds to support private schools, and Leicester Academy was effectively taken over by the town of Leicester. Today Leicester High School is located directly behind the former location of Leicester Academy. Some of the former property of Leicester Academy was taken over by Leicester Junior College and later Becker College, as described above. Most of the property was once part of Lot Number 1, the Stebbins property described earlier where Sewall visited and the May House is also located. Today, a few of the buildings of Becker College have been taken over by the high school. There is much more I could write about this section of Washburn Square, including the curious diminutive Colonial Revival Pump House building that sits on the northeastern corner of Washburn Square, or the interesting history of some refugees from Newport, Rhode Island, who settled in Leicester during the Revolutionary War, including Aaron Lopez, a Jewish merchant (and slave trader) on whose land and mansion, which was the original building, Leicester Academy was started.³² However, in the interest of progress, I will curtail my urge to say more, and continue a few steps west across Washburn Square, to investigate another building and some artifacts with a direct connection to the history of the Upper Boston Post Road.

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Hiram Knight House seen from Leicester Common across Paxton Street. The front of the building was built around 1842, but the rear ell is reputed to be the remnant of the Swan Tavern, built to replace the previous tavern which burned in 1767. The first tavern in Leicester was established at this location by Nathaniel Richardson in 1721.

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Local Hospitality

The Swan Tavern/Hiram Knight House in Leicester. Some sections of the original tavern building from 1767 still remain as part of the house built in 1842 for Captain Hiram Knight, a businessmen who owned one of the many textile factories which thrived in nineteenth-century Leicester.

My favorite document pertaining to the Upper Boston Post Road is, without doubt, the Vade Mecum for America: Or A Companion for Traders and Travellers, published in 1732 by Thomas Prince (1687-1758), minister of Old South Meeting House in Boston. This fascinating early travel guide lists taverns along the major roads leading out of Boston, including the road “from Boston, westward thro’ Worcester to Springfield on Connecticut River.” The “Publick Houses” are listed sequentially, with a number providing the distance in miles from the previous tavern and a second number providing the distance along the road from the “Town House” in Boston, in other words,the Old State House at the corner of State Street and Washington Street. A final column provides the name of the “Towns or Places” in which the taverns are located. Leicester appears in the list of towns along the route of the Upper Boston Post Road in the Vade Mecum. Richardson’s tavern in Leicester is located fifty miles from Boston and six miles from Jennison’s, the previous tavern listed along the road, in Worcester. The terse nature of the entries of the Vade Mecum belie the wealth of information they provide about the route of the Upper Boston Post Road.

Samuel Sewall’s record of his travels in the decades preceding the publication of the Vade Mecum illustrate how much had changed in thirty years. Sewall did not stop in 1698 because there was no settlement in Leicester at the time, and he stopped at “Stebbing’s” on “Strawberry-Hill” in 1716 and again in 1718 because the town was only just being settled and no tavern or “Publick House” had yet opened to provide for travelers. That this had changed by 1721 is clear as, during the selection of the Reverend David Parsons as the first minister of the church in Leicester, “Mr. Parsons, it appears, was then in waiting at the public-house kept by Nathaniel Richardson, which stood where Captain Hiram Knight’s house now stands. He was accepted March 30, 1721.”³³ Emory Washburn, the first historian of Leicester, states unequivocally that “the first in order of time was one standing where Captain Knight’s house is, at the corner of the Great Road (now Main Street) and the Rutland Road (now Paxton Street). It was early built, and occupied as a public-house from the first. The first occupant was Nathaniel Richardson, as early as 1721.”³⁴

Richardson, like Stebbins, was another of the early settlers, and he acquired at least two of the lots in the original disbursement of property. One of these was in the area where St Joseph’s Church stood until recently, a lot where he built a house in which another tavern was established in 1726 by his daughter Deborah and her husband Jonathan Sargent, as I discussed in the previous entry. Richardson also built a house on the other property, bordering the Common on the west, which was the first tavern in town. Washburn provides a history of the ownership of the tavern over the years: “John Taylor owned and occupied it in 1746. He sold to John Taylor, jun., in 1755. In 1756, it was kept a short time by Seth Washburn. He appears to have been succeeded by Mr. Taylor again. Benjamin Tucker occupied it in 1761, and, by permission of the town, dug a well upon the Common, now remaining,—“a little west of the sign-post.” The house then belonged to the estate of Mr. Taylor, who had died. It was soon purchased by Edward Bond; and while in his possession, in 1767, was burned, as stated in another part of this work. The house was rebuilt and occupied by Mr. Bond until 1775, when he sold it to Isaac Kibbe; but I apprehend he never lived upon it. It was kept by Elijah Lathrop from 1776 to 1778 when Peter Taft, from Uxbridge, who had purchased of Kibbe, occupied it till 1781. He then sold it to Reuben Swan, who enlarged it, and continued to occupy it until 1801 when William Denny purchased and occupied it till about 1810. He was succeeded by Aaron Morse, who occupied it until he removed into the tavern opposite the Meeting-house.”³⁵ Curiously, according to a genealogical history of the Richardson family, Nathaniel Richardson died “intestate, not far from the close of 1728.”³⁶ If true, then it is curious that the tavern was still called Richardson’s in 1732. Nathaniel Richardson had a son, also called Nathaniel, who lived in Boston, and he died young in 1730. Other sons seem not to be associated with the tavern, so it seems likely that his widow Abigail, who was the administrator of Nathaniel Richardson’s estate (along with their son Nathaniel who died shortly therefater himself) and who did not remarry, ran the tavern herself until John Taylor took over sometime before 1746. Abigail Richardson died in 1759.

Thompson House (c. 1922) at 1019 Main Street, Leicester. Although it is not a particularly significant house architecturally among the Main Street row of elegant houses, this house was built on the site of the Leicester Hotel, a competitor to the nearby Swan tavern and an important stop along the route of the Upper Boston Post Road from the 1760s until it burned in the early twentieth century.

Reuben Swan, one of the later owners, is the name currently associated with a group called the Friends of Swan Tavern which, according to their Facebook Page, is “a group dedicated to establishing and maintaining a historical museum in one of Leicester’s most iconic buildings! Through the Leicester Historical Commission, the Town of Leicester has retained the Swan Tavern for this purpose. The Commission, in partnership with the Leicester Historical Society, will establish this museum with rotating historical displays and educational programs.” The Friends took over the building which had been acquired by Leicester Junior College in 1965 and previously had served as the administration building for Becker College before its closure in 2021. The Washburn Square Report refers to the building as the Swan Tavern/Hiram Knight House (1842; LEI.116), but Washburn states that the tavern was located “where Captain Hiram Knight’s house now stands,” implying that the tavern had been replaced by the house. This apparent contradiction is resolved by the discovery that parts of the Swan Tavern were incorporated into the house built around 1842 by Hiram Knight.

The Hiram Knight House (1842; LEI.116, see photo above and at the beginning of the entry) is an elegant Greek Revival mansion on the western edge of Leicester Common. Hiram Knight (1794-1875) purchased the original building in 1823 “and for about two years he lived there, did butchering, kept the tavern, and for a time was associated with Reuben Merriam in card making and a store.”³⁷ Knight became a successful manufacturer and businessman, a topic to which I will return in the next entry, and decided to build a large modern house along the main road where the tavern was located in 1842. Although the Greek Revival house facing Main Street was built in the 1840s, apparently the rear section of the house “is the ell of an 18th-century tavern, the main block of which was demolished to make way for the present Greek Revival-style house. The broad eaves and Greek Revival-style door and window frames link the ell to the newer section, yet the close eaves on the rear gable end are a hint of an earlier date of construction for this section.”³⁸ On a chilly day in December, I am fortunate to be given a tour of the mansion by Don Lennerton, a gregarious and knowledgeable local historian, a retired long-time Leicester police officer, and past President of the Leicester Historical Commission. Inside the interesting building it is obvious that the front and the back of the house are of two different architectural styles: not only is the front grander and more architecturally detailed than the rear section of the building, but also, on the second floor, a step down is required to get from one section of the building to the other. Don Lennerton also told me that the front of the original Swan Tavern building, rather than being demolished, was moved to a location at what is now 43 Willow Hill Road, an older section of the original Upper Boston Post Road in Cherry Valley, which I discussed in the previous entry. The undistinguished building at 43 Willow Hill Road could be the front of the tavern but has been modified so substantially over the years that it is hard to recognize an old building in the current house at the location. However, as I have discovered over the course of this project, moving buildings was not an uncommon practice in the nineteenth century, so it is plausible that the nondescript exterior is obscuring the eighteenth-century tavern building.

Despite the fact that I have not found any evidence of illustrious visitors like George Washington or John Adams staying at the tavern (although Adams did stay at Sargent’s Tavern, as I discussed in the previous entry), I have found an occasional reference to the tavern and to later owners in some of the primary sources at my disposal. A fascinating early mention of the tavern is in a journal from 1728 in the possession of the Massachusetts Historical Society (MHS), which can be accessed online. According to the description on the MHS website: “Dudley Woodbridge (1705-1790), a physician from Groton and Stonington, Connecticut, kept this journal from 1 October to 10 October 1728 while traveling with Ebenezer Hinsdell (Hinsdale) from Cambridge to Sunderland, Massachusetts. Within this 5-page journal Woodbridge described and sketched various meeting and dwelling houses in Watertown and Deerfield, Massachusetts; ministers and lay people visited; the landscape; constellations; and objects of note, such as a Native American bier.” In a truly interesting entry (albeit difficult to read; the bracketed statements are my interpretation of what he wrote), on October 2, 1728, Woodbridge and Hinsdale made their way through Worcester and, after crossing “Halfway river [3?] and 1/2 more miles brought us to Richardsons at Leicester @ 1/2 after 7 a clock of Evening- gave [aforementioned?] charge of our horses & having supped we went to bed Early but slept very little. We awoke about 1/2 an hour after 4 in the morning and walking out abroad were surprised with a very bright Aurora Borealis the lights from NE to NW Streaming up in white streaks almost top ye Zenith variable [tinctured?] A Glowing red light so great that our shadows were plainly visible on the Earth it continued to ye light of morning came on. We paid our Richardson and set out about 5 a clock we left Mr Parsons [at?] The meetinghouse (d) on ye right hand on a hill.” One point to revisit here is that this narrative indicates Nathaniel Richardson was still alive in early October, 1728, consistent with the statement in the genealogical history that stated he died “not far from the close of 1728.” Had the “Richardson” in question in Woodbridge’s narrative been Abigail Richardson, Woodbridge would surely have referred to her as “the widow Richardson” or “Mrs.” Richardson, rather than with the off-hand phrase “our” Richardson.

*John Sargent Store and Post Office (1829), 1025 Main Street, Leicester.*

The “Halfway River” is a reference to Beaver Brook, which passes through Webster Square in Worcester and is visible, as “Half-way River” on the 1795 map of Worcester. The distance from the bridge in Webster Square to the Richardson/Swan Tavern is about 4.1 miles, a little more than the 3.5 miles recorded by Woodbridge. It is, however, the exact distance to the former house of Nathaniel Richardson, which became the Sargent tavern sometime after 1726. The entry by Woodbridge thus somewhat muddies the water. The way Woodbridge phrases this passage implies that they passed the meetinghouse after they set out from Richardson’s, which suggests that the tavern that he stayed at was in fact the tavern that became Sargent’s and that Richardson either was still at the first location in 1728 or that he operated two taverns, one at each property. Washburn is unequivocal about the location of Richardson’s, but he was writing in 1860. Perhaps there was a little more complexity in the early history of the first tavern in Leicester.

Parsons is, of course, the Rev. David Parsons, who waited in Richardson’s seven years earlier prior to his selection as minister of the aforementioned meetinghouse, which was originally located directly across Paxton Street from the current location of the Knight House/Swan/Richardson Tavern. Parsons was a frequent topic in the diary of Reverend Ebeneezer Parkman, minister of the church in Westborough, who kept a diary for many decades beginning in 1719. Another topic that will have to be shelved in the interest of progress, a long-running dispute between Parsons and his congregation brought ministers from other towns into Leicester, including Parkman, in an attempt to settle what Parkman referred to, in a diary entry from September 3, 1728, as “the Council upon the Difficulties at Leicester.”

Parkman also mentions a later owner of Richardson’s tavern. In 1770 Parkman was involved in a property transaction in Cherry Valley, involving his son Alexander Parkman, which I discussed in the previous entry. On February 12, 1770, Parkman records a visit to Leicester with his son in which Parkman goes “up to Mr. Conklin’s who is ill of Rheumatism, and lodge there. Alexander to the Tavern (one Bond’s).” This reference is clearly to the new tavern, rebuilt to replace “the public-house of Edward Bond, situate where the house of Capt. Hiram Knight now stands, was burned, with all its contents of provisions and furniture, on Sunday, the 18th January, 1767.”³⁹ “Mr. Conklin’s” is a reference to Benjamin Conklin, minister of the church in Leicester from 1763 to 1794, when failing health forced him to resign.⁴⁰ Conklin lived at the time, according to the description of Leicester Center in 1767 by Washburn that I included earlier, in the house “built by Mr. Stebbins and afterwards owned by Mr. Conklin,” on the property “where Mr. May lives.”⁴¹ Conklin is frequently mentioned by Parkman in his diary, as they were colleagues, and Parkman usually stayed at Conklin’s house when in Leicester. The mention of the tavern is the only time Parkman refers to a tavern in Leicester.

*Daniel McFarland Store (1809), 997 Main Street, Leicester*

Other mentions of the tavern and its later owners, as well as other taverns established in Leicester in the intervening decades, are found principally in the treasure trove of almanacs published from the late eighteenth century and into the early nineteenth century. Isiah Thomas published an almanac for many years after his removal to Worcester in 1775. The 1785 edition of his Almanack lists the Swan Tavern in Leicester on the “Western Post Road to Hartford, Fish-Kill, and Philadelphia,” 3 miles from Jones Tavern in Worcester, which was 3 miles distant from the previous tavern in Worcester, Campbell & Stowers. Campbell & Stowers was located on the northeastern corner of Elm Street and Main Street in downtown Worcester. Jones was located at the junction where Main Street and Apricot Street separate near the Leicester border. The distance along the road according to my calculations from the Swan Tavern to the site of Jones Tavern is 3.1 miles and to the site of Campbell & Stowers is 6.3 miles, both very close to the distance provided by Thomas. Following Thomas’s math, the distance from Boston to the Swan Tavern is calculated at 53 miles. According to the calculations based on the route I have followed thus far from Boston, the Swan Tavern is 53.5 miles from Boston.

Samuel Stearns’s Almanack for 1788, Bullard’s Almanack for the Year of Christian Aera 1790, and Bickerstaff’s Genuine Boston Almanack for 1791 all list Swan in Leicester at approximately the same distance from Boston (the almanacs are often slightly off from each other in their calculations!). Nathanael Low lists Swan in both his 1795 Almanack and in his 1800 edition. Swan is not listed in any almanac after 1800 that I have examined, consistent with Washburn’s assertion that he sold the tavern to William Denny in 1801. As I will discuss shortly, there were other taverns and hotels nearby by that time which may have successfully competed for the “Almanack” slots, as other taverns both in the center of Leicester and further along the road are often listed in other almanacs published before 1800 while Swan’s is frequently omitted.

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High Mile

Milestone marker on Leicester Common which reads “54 Miles From Boston.” This milestone, at 1013 feet above sea level, is located at the highest elevation thus far along the first 53.5 miles of the route of the Upper Boston Post Road from Boston. It was lost, recovered, and moved here from a nearby location as discussed in the main entry.

The previous stop along the road from Richardson’s in the Vade Mecum from 1732 is Jennison’s. As I discussed in a previous entry, this is most likely a reference to the house of William Jennison, located close to the Worcester County Courthouse. The Courthouse also happened to be the location from which distances were measured in Worcester County. All of the maps of towns produced in 1794/1795 as a result of a decree by the General Court were required to report the distance from the town center to both the county seat (i.e., the county courthouse) and the State House in Boston.⁴² The location of the “congregational meeting house” in the center of the town of Leicester, as shown on the official map of Leicester produced by Peter Silvester, Jr. in 1795, is listed as “7 miles from Worcester court house” and “54 miles from Boston.”

The first thing to notice is that the Vade Mecum lists Jennison’s as 44 miles from Boston and Richardson’s as 50 miles from Boston. This is an error which began after Shrewsbury, where Prince clearly made a 2-3 mile miscalculation which was perpetuated all the way to Springfield, which he shows as 94 miles from Boston but which, on the 1795 map of the town surveyed by Israel Chapin, is shown as “96 1/2 measured miles.”⁴³ Many of the almanacs, including the ones published decades later discussed above, often have inconsistent calculations in their lists, a hazard of the days before GPS and Google Maps. The second point to make is that, as Jennison lived near the courthouse and Richardson’s was opposite the meeting house in Leicester, the distance between the two locations must have been seven miles as indicated by Silvester’s map. Following the original route of the Upper Boston Post Road as closely as possible, I have calculated the distance between the two locations as 6.7 miles, which is within the margin of error. The 1795 map of Worcester by David Andrews and John Peirce states that “the distance from Boston to Worcester Court-house is 47 miles.” Silvester reports the distance to Boston from Leicester as 54 miles, which is consistent with the calculations on the Worcester map.

As it happens, very near to the Swan Tavern and the original site of the meeting house is a stone mile marker indicating “54 Miles From Boston” (see photo). This milestone marker is located in the grass of Leicester Common on the north side of Main Street, opposite 1003 Main Street, the Colonel Thomas Denny Jr. House (1791, LEI.85), a house to which I shall return shortly. The milestone is of sandstone, a material which many of the milestones in this area have in common, and is somewhat eroded and pockmarked, with slightly worn lettering. There is no date listed on the stone nor are there any initials visible which might suggest a possible carver. These stones are often referred to as Benjamin Franklin Milestones and are purported to have been placed around 1767 (see the 1971 National Register of Historic Places Inventory Nomination Form, which refers to the entire series as the “1767 milestones,” a statement immediately disproved by looking at any number of milestones with much older dates engraved upon them). As I have stated on many previous occasions, I also do not believe these were placed by Benjamin Franklin. However, the milestone is very likely to have been in existence before the 1790s when the route of the Upper Boston Post Road was shortened, initially by the construction of the Charlestown bridge over the Charles River from Boston to Cambridge, and then by subsequent bridges built over the river in the following few years, reducing the distance west from Boston by more than two miles.

*John Whittemore House (c.1800) at 1033 Main Street in Leicester, Massachusetts. The sandstone insert in the wall is discussed below.*

As I have discussed in previous entries, the “47 mile” stone, currently located in front of the Oaks mansion on Lincoln Street in Worcester, was moved and was originally located closer to the old Worcester County Courthouse. The “54 mile” stone is located about 7.2 miles from the “47 mile” stone, but is almost exactly seven miles (6.9) from the previous location of the “47 mile” stone on Old Lincoln Street in Worcester. The “54 mile” stone is located 6.7 miles from the old Worcester County Courthouse on the corner of Main Street and Highland Street in Worcester. According to my calculations, like the Swan tavern and the “Congregational meeting house” shown on the 1795 map of Leicester by Peter Silvester Jr., the “54 mile” stone is about 53.5 miles from the Old State House in Boston. It would appear to be within the rounding distance but just barely. As it turns out, the “54 mile” stone is not in its original location, and the peripatetic journey of the milestone to this spot on Leicester Common is quite an interesting story.

The Washburn Square Report discusses the history of the milestone: “The general location of a milestone that once stood along the road is recalled by a blank piece of sandstone in the stone wall (LEI.901) in front of the John Whittemore House (c.1800; 1033 Main Street; LEI.81). The original milestone was one of six identified in Leicester. (See 1971 Thematic NR: 1767 Milestones.) The milestones—sometimes called Franklin markers—were placed along the Boston Post Road under the administration of Postmaster General Benjamin Franklin in order to facilitate the calculation of postage rates. The original marker, which has “54 miles to Boston” inscribed on it, was stolen in the mid-1930s. In 1996, it was found and placed in the museum of the Leicester Public Library. While the stone wall reportedly dates to the late 19th century, the sandstone insert must post-date the 1930s if it was in fact put in place to recall the milestone.”⁴⁴

Reproduction of the image showing the milestone in the 1971 report on the “1767 Milestones” (see main text for discussion). The milestone is embedded in a slab on the top of the wall to the left of the gate (see second photograph below). Notice that neither the house nor the wall remotely resembles the house at 1033 Main Street in the photograph above.

In a publication coordinated with the 275th anniversary of the founding of the town of Leicester, entitled Where the Wild Strawberries Grow: A Pictorial History of Leicester, the authors discuss the house at 1033 Main Street, opposite the Knight House/Swan Tavern. This house still has the wall in which there is a blank sandstone insert on the west-facing side (see photo). The John Whittemore house “was bought from Daniel MacFarland…and, in 1820, enlarged to its present size.”⁴⁵ There is a photo of the house in 1997 and another photo purporting to be from 1890 showing the same house, with a caption stating that the “mile #54 marker…was in the stone wall pictured next to the front lawn. It disappeared from the site several years ago.” The house in the 1890 photograph, to be honest, looks nothing like the house in the 1997 photograph, and neither the stone nor the wall is clearly visible in the earlier photo, but the statement that the stone disappeared some years ago is consistent with the Washburn Square Report.

On the other hand, The 1971 Milestone Report has a record of the “54 mile” stone, along with photographs of the wall in front of the house and of the stone inlaid in the wall. The stone, rather than being inserted into the west-facing wall, is instead inserted into a slab that acts as a capstone for the wall, adjacent to a metal gate, on the left side of the wall as viewed from the street (see the photos). The text below the photograph states that the location of the “54 mile” stone is on the “north side of Main Street, easterly of Paxton Street near Leicester Junior College.”

*The “54 mile” stone, embedded in what might be concrete, sits atop a wall on the property at 101 Pleasant Street. How it got there is still a mystery.*

Although the stone in the photograph is clearly the “54 mile” stone, the house in the photograph is not the house at 1033 Main Street: it does not look like the house at all, the wall is completely different, and the report states that the house is on the north side of Main Street while 1033 Main Street is on the south side of the street. I searched in vain for a house along Main Street that corresponded with this house and found not one that was a reasonable candidate. I am happy to report that Don Lennerton sorted the story out for me. Although some of the details remain shrouded in mystery, I can report that Don Lennerton himself was involved in the recovery of the stone and in the storage of both this milestone and of milestone 52, which is currently inserted in a wall on Main Street in Cherry Valley, as discussed in the previous entry.

The upshot is that, at some point, the “54 mile” stone went “missing” from its location on Main Street. There was a significant amount of road work along Main Street and South Main Street in the early 1930s (discussed in the next entry), so perhaps the stone was removed for safekeeping and, for some reason, never returned. The location of the stone was known to some people as there is clearly a photograph of it and the house at which it was located in the 1971 milestone report. The clue is in the caption which states that the owners are “Tr.s of Warren Lane” which I believe means the trustees of Warren Lane. A Worcester attorney, Warren C. Lane, Jr. (1923-2021) grew up in Leicester and was a longtime trustee of Becker College. It appears that the family owned the property at 101 Pleasant Street, which is the house shown in the milestone report. This is obviously not on Main Street, so the report was clearly wrong about that detail. However, the wall and the house (viewed from Wesley Drive) are clearly the same as the one in the photograph (compare the images above and below). The “54 mile” stone somehow mysteriously ended up embedded in a slab of what appears to be concrete and was placed on top of the stone wall in front of the entrance to the house, which is located on Wesley Drive, just off Pleasant Street.

This house and the wall in front, at 101 Pleasant Street in Leicester, seen here from Wesley Drive, is clearly the house shown above in the 1971 milestone report. The “54 mile” stone was recovered from this location, stored for some years, among other places, in the museum of the Leicester Public Library, and placed, in 2016, in its current location along Main Street on Leicester Common.

To summarize a long story, the stone was transported to this house at some point, perhaps in the 1930s, from its original location, which was presumed to be on the wall of the Whittemore House at 1033 Main Street, opposite the the Swan Tavern. At some point the sandstone insert was placed in the wall at the Whittemore house to indicate the location of the lost/missing/stolen stone. Somebody clearly knew of the existence of the stone around 1971, and that it was the “property” of Warren Lane, because it appears in the 1971 milestone report. The stone was later placed in a barn on the property. Around 1996 the stone was “recovered” and later placed in the museum on the second floor of the Leicester Public Library (a great little museum if you are in town, by the way). Twenty years later the Massachusetts Department of Transportation embarked on a program to rehabilitate, restore, and reposition historic milestones along the Post Road from Boston. Hence, in the summer of 2016, the stone was placed on Leicester Common, where it sits today, welcoming passing visitors along the route of the Upper Boston Post Road. It might not be the exact location of the original milestone, but at least it is not hidden away atop a wall or in a barn on a side street hundreds of yards off the road. Don Lennerton, along with milestone “54” in its new location, was prominently featured in a Boston Globe article from 2017 about the restoration of the milestones along the route of the Upper Boston Post Road by the Massachusetts Department of Transportation, a fitting tribute as he played a major role in the recovery of the stone and in the subsequent promotion of this and other milestones in the town. I have also included a photograph below of the 1996 article from the Worcester Telegram and Gazette describing how the stone (along with the “52 mile” stone) was recovered.

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An article from the Worcester Telegram & Gazette documenting the recovery of the “54 mile” (and the “52 mile” stone reproduction), which were stored in a barn at 101 Pleasant Street, about half a mile away from its original location. Today they are installed near their respective original locations in Leicester. Thanks to Don Lennerton for providing the clipping.

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Squaring Up

*David McFarland House (1813), 933 Main Street, Leicester*

I spent several hours with Don Lennerton, a man who has lived his entire life in Leicester and who has a deep interest in the history of the town. I could not possibly include in this project everything about Leicester that he knows or even a fraction of what he told me in our short time together, as it would expand beyond the scope a trip along the road into something much bigger. This project is already too ambitious as it is. Additionally, as I stated earlier and is clear from the murky story of the “54 mile” stone, there is a lot to know but there is also a lot that is likely to remain unknown. At some point I need to leave the mysteries of the town to the very capable local historical sleuths to work out. Perhaps someday there will be a development in this story and other stories and an addendum can be added to this entry.

Part of the point of this project is to collect the local histories of the towns along the route of the Upper Boston Post Road in one place so that others might be able to use this site as a starting point for their own research. I am a traveler when all is said and done. When I leave town people like Don and Joe Lennerton in Leicester, or Norm Corbin in Northborough, will continue to research the history of their respective towns. Every step I take along the route of the Upper Boston Post Road is made possible by the selfless work of local historians quietly researching and recording the stories of their patch of the road. Their research has improved my project and I am thankful for their efforts.

However, I need to get out of Washburn Square and continue along the road through Leicester. This entry will conclude just past the Swan Tavern, where Main Street, Pleasant Street, and Route 9 merge at a busy intersection marking the beginning of the modern center of the town of Leicester. The next entry will begin with a discussion of how the town and the center evolved, and then continue west through the last 2.8 miles of the town to the border with Spencer. Before leaving Washburn Square it seems appropriate to finish the discussion of the buildings located on the square, especially as, thus far, only the buildings facing the east, north, and west sides of the Common have been discussed, while the buildings along the south side have been largely neglected. The fact that these buildings line Main Street, the southern edge of Washburn Square and the actual route of the Boston Post Road, and the fact that the buildings are some of the most interesting from a historical and architectural perspective makes it doubly important to spend a little time reviewing the dozen or so buildings along this short (1000 foot) section of the Upper Boston Post Road, before ending this entry.

The Washburn Square Report concisely summarizes the early development of the area around the Common: “During the first half of the 18th century, dispersed farmsteads characterized most settlement in Leicester; however, as the information presented above suggests, some clustered settlement was occurring in the area of the common. By 1767, the Swan Tavern, a schoolhouse, shoemaker’s shop, minister’s house (north of the meetinghouse), the Stebbins House (site of 960 Main Street), and a few houses further east were known to cluster around the meetinghouse….During the late 18th and 19th century settlement continued to cluster in the district locale. Important sites from this period include the Leicester Hotel that stood from 1794 to 1892 on the site of the 1761 tavern at 1019 Main Street until it was destroyed by fire.”⁴⁶

*Southgate-Whittemore-Smith House (1826), 1041 Main Street, Leicester*

The tavern referred to in the report was a second tavern on Washburn Square that was opened by Nathan Waite in the 1760s (the report says 1761 in one place and 1766 in another, Washburn says 1776, which is probably incorrect as well). Waite ran the tavern here until 1776, when he moved to take over the Sargent tavern after the death of Phinehas Sargent, at the building put up by Richardson on Main Street near what is today Waite Street close to what is today called Waite’s Pond. The tavern in Washburn Square was replaced a few years later by the Leicester Hotel, which was in operation from the eighteenth century until it burned in the 1890s. According to Amos Hill Coolidge, writing in 1890, “here a hotel has been kept by successive landlords to the present time. Among these was John Hobert, who had charge of it from 1799 to 1817, and gave to it a wide-spread reputation as an excellent hostelry.”⁴⁷ A “Hobart’s” is listed in Isiah Thomas’s Almanack of 1802, 6 &1/8 miles beyond Mowers in Worcester, which is about right, since Mowers was located directly across the street from what is now City Hall in Worcester. Washburn is more detailed in his description: “the house has been kept as a hotel by various persons, among whom were Mr. George Bruce and Mr. Bugbee; Abner Dunbar; Johnson Lynde, in 1797-8; Arad Lynde, his son, and Nathan Felton, 1799 when John Hobart purchased it, and carried it on with great success till about 1817. When he first took it, it contained but two front-rooms and a kitchen and bedroom in the body of the house. He enlarged it from time to time to its present size. He sold the estate to Alpheus Smith under whom Aaron Morse occupied as a tenant until his removal to New Haven about 1822.”⁴⁸

In the 1795 edition of his Almanack, Nathanael Low lists Dunbar’s in Leicester, six miles past Mower’s, while Swan’s is one mile further along, which seems a bit too far as the two are only yards apart on the Common, but he fixed the math by the 1800 edition where, although Lynde is listed as the owner instead of Hobart, Lynde and Swan are both seven miles further along from Mower’s in Worcester.⁴⁹ Many of the tavern owners moved from one tavern to another in Leicester and in other towns. George Bruce is listed above by Washburn as one of the owners of the Leicester Hotel but he also operated a tavern about a mile down the road at some point, which will be discussed in the next entry. The same is true of Aaron Morse, as well as of Peter Taft and Elijah Lathrop, who were associated with the Swan tavern and other locations in Leicester, and of Abner Dunbar, who also operated the tavern at Mount Pleasant, a mile west of the Common.

A newer Leicester Hotel was built in 1894 that can be seen on the 1898 map of the Common. This hotel went by various names, including the Brown Owl Inn and the Leicester Inn (as seen on the Sanborn map of 1910), until it too burned in 1914. The tavern and hotel were located at 1019 Main Street; today the Tudor Revival-style Thompson House (1918-1931; LEI.84) is located on the site. This house is probably the least interesting house from an architectural point of view, although, as we have seen, the history of the location is of of great significance in the context of the Upper Boston Post Road.

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*Colonel Thomas Denny House, 1003 Main Street, Leicester. The house, built in 1791 for card manufacturer Thomas Denny, was later used by Becker College and was called Winslow Hall.*

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Ten buildings line the Common on the southern side of Main Street from Flint Way in the east to the junction of Main Street with South Main Street/Route 9 and Pleasant Street. Two more buildings, both west of the Swan Tavern along the north side of Main Street, are included in the Washburn Square Report, marking the western boundary of the Historic District. Much like the Thompson House, not all of the buildings are of particular architectural interest, but their locations all have long and rich historical significance to the development and history of Leicester. Again, I cannot afford to spend as much time as I would like on each house, but a couple of them are worth a mention before I move on, while others are shown in photographs scattered through the entry. The first house along the elegant row encountered from the east is the Sprague-Flint-Denny House (1812; 981 Main Street; LEI.88), which is one of the buildings shown in a photograph earlier in this entry. Also shown in a photograph above is the neighboring house to the west, which is discussed in detail in the Washburn Square Report: “the grandest Federal-style house in the historic district, as well as in the surrounding area, is the five-bay, center-entry, hip-roofed David McFarland House (1813; 993 Main Street; LEI.87), which occupies a prominent location opposite the common. Dating to 1813, it is built of brick and is painted white with paired interior chimneys at each end. In the manner of an Italian palace, from which Federal-style houses of this type were derived, it is three stories high and has smaller windows at the third level.”⁵⁰ Next door, at 997 Main Street is another Federal-style building, the Daniel McFarland Store (1809; 997 Main Street; LEI.86).

The next house to the west is labelled Winslow Hall, another of the buildings formerly used by Becker College. This building was originally built in 1791 by Colonel Thomas Denny (1791; 1003 Main Street; LEI.85), who moved here from his family estate overlooking the Blackstone River Valley upon what is now Denny Hill, as I discussed in the last entry. Denny was an important early manufacturer in the town of Leicester, and his move is an illustrative example of the changes which occurred in Leicester after the Revolution. I will return to Denny and to Knight, another successful businessman and manufacturer, in the next entry, but I have included a photograph (above) of his house in this entry. The Thompson House, which has already been discussed, is the next house located along the row. The building on the west side of the Thompson House, “the brick Post Office and Sargent Store (1829; 1025 Main Street; LEI.83, see photograph above) was built by John Smith in 1829 for storekeeper John Sargent, Jr., who was Leicester’s second postmaster. He succeeded his father, Henry Sargent, who operated Leicester’s first post office, established in 1798. Darius Cutting, who lived next door, once had a hat shop on the site of the Post Office and Sargent Store. The building is now residential.”

The neighboring Darius Cutting House (1789; 1029 Main Street; LEI.82) is the oldest surviving and best-preserved house along the row, and was moved ten feet to the west in 1829 to accommodate the Sargent Store. The neighboring house to the west, at 1033 Main Street, is the John Whittemore House, where the “54 mile” stone was presumably located originally and where the blank sandstone insert is located today (see photo above). As I was taking an image of the sandstone insert in the wall I met the owner of the house as she waited outside for her child to get home from school, after which she graciously showed me around the property as her young son gamboled around in the yard in front of us.

*Darius Cutting House (1789), 1029 Main Street. The oldest and best preserved of the houses along Main Street facing Leicester Common.*

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The tranquility of Washburn Square is disrupted at this point, as traffic from the busy junction of Pleasant Street, Main Street, and South Main Street (Route 9) feeds into Paxton Street. After passing the former site of Leicester Police Station, originally built as the Old Town Barn (1930; 1037 Main Street; LEI.80), there is one more elegant house along the south side of Main Street, the transitional Federal-Greek Revival Southgate-Whittemore-Smith House (1826; 1041 Main Street; LEI.79). This lovely brick house is located on the busy corner where Main Street and South Main Street/Route 9 merge. Directly across Main Street and west of the Swan Tavern, at 1044 Main Street, is a much-disfigured but still recognizably Greek Revival-style building, the Cheney Hatch House (1842; 1044 Main Street; LEI.78), which today houses Leroux Liquors on the now very busy intersection. The J.A. Smith Building (1801; 1058 Main Street; LEI.76), just west of the liquor store, “anchors the west end of the historic district.”⁵¹ This stately building, with an unfortunate commercial building dating to the 1920s (1054 Main Street; LEI.77) growing off its east end, seems somewhat out of place in this setting, overlooking the traffic moving through this busy intersection. However, the owners of all the houses at this intersection, J.A. Smith, Isaac Southgate, and James Whittemore, along with Thomas Denny and Hiram Knight whose nearby houses overlooked Leicester Common, were all involved in manufacturing, and their factories once surrounded the square as we shall see in the next entry. The tranquil Washburn Square of today was not always so peaceful; it was once a much more industrially-oriented neighborhood, with shops and factories interspersed all around the houses that survive from that era. The busy area west of the Common was a byproduct of this concentration of industry; the money the factories earned was used to build many of the houses along the Common, as well as many of the commercial and residential buildings that line Main Street as it heads west to Spencer from Washburn Square. I will discuss all this in the next entry as I make my way through the rest of Leicester along the route of the Upper Boston Post Road to Spencer. Although I am leaving the Leicester Center National Register Historic District, there is still plenty of history to discover along the road west.

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*The house anchoring the west end of the historic district: The J.A. Smith House (1801) with an addition from the 1920s, 1058 Main Street, Leicester.*

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Special thanks to Don Lennerton, who gave generously of his time and his knowledge of the history of Leicester; thanks also for giving me the “inside story” of the wandering milestones.

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Distance traveled in this entry along the route of the Upper Boston Post Road: 0.5 miles.

Total Distance traveled thus far along the route of the Upper Boston Post Road from Worcester Courthouse to Springfield “Meeting House” (seven entries): 6.8 miles.

Total Distance traveled along the original route of the road from the Old State House in Boston for this project: 53.5 miles.

Total Distance covered for all the walks described in Boston Rambles: 115.1 miles

Posted in History, Milestones, Roads, Upper Boston Post Road on 19 December 2025 and tagged Leicester, Milestones, Old Roads, Taverns
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Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Leicester, Massachusetts, #2.

Savoring the Fruits of Leicester

Part Two- A Walk Up Strawberry Hill

Upper Boston Post Road #21 (UBPR #21).

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Leicester, Massachusetts, #2.

Savoring the Fruits of Leicester

Part Two- A Walk Up Strawberry Hill

Upper Boston Post Road #21 (UBPR #21).

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