Leicester, Massachusetts, #1.

Savoring the Fruits of Leicester

Part One– A Walk Through Cherry Valley

Upper Boston Post Road #20 (UBPR #20).

Looking east up Sargent Street in Leicester, the original route of the Upper Boston Post Road through Cherry Valley. The house in the photo might be the Asa Sargent house shown on E.M. Woodford’s 1855 map of Leicester.

“The township is principally composed of lofty hills, with deep vallies between them. The hills are generally considered as the highest ground between Connecticut River, and the Shore.”

Timothy Dwight, Travels in New England and New York (1821), p. 364, writing about the town of Leicester, Massachusetts.

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Introduction

Reverend Amos Hill Coolidge (1827-1907), minister of Leicester First Congregational Church from 1857 and author of A Brief History of Leicester, Massachusetts, published in 1890, states that, in 1714 “Leicester was then an unbroken wilderness. Worcester was just beginning, for the third time, to be resettled. There was no settlement of whites, except Brookfield, between Leicester and the Connecticut River.”¹ Leicester and all the towns between Worcester and Springfield, with the notable exception of Brookfield, which was settled in the 1660s and subsequently destroyed during King Philip’s War, are relatively recent settlements compared to the towns in and around Boston, which had in some cases been inhabited by English settlers for nearly a century at the time of the settlement of Leicester. This area was thus, quite literally, the frontier in the early eighteenth century and the Upper Boston Post Road at the time was primarily a road through the wilderness. Even today the area is quite distinct in many ways from the Boston metropolitan area (of which it is technically but tangentially a part in only the loosest definition of a metropolitan area, as I discussed in the previous entry), including topography, population density, and even political orientation, as we shall see. The fifty-mile walk from Worcester to Springfield promises to be a very different walk from the first fifty-mile walk from Boston through to Worcester.

In the previous entry about my journey along the route of the Upper Boston Post Road I provided an overview of the roughly fifty-mile walk from Worcester to Springfield. I also noted that the walk from Worcester to Springfield begins at Worcester County courthouse and continues for a little over four miles through Worcester before reaching Leicester, the first of the eleven towns through which the road passes between Worcester and Springfield. Leicester is much more closely connected to the city of Worcester than any of the other towns along the route, not just because the two towns share a border, but also because the geography of the eastern part of Leicester is oriented toward the city of Worcester. The town also shares its Congressional representation with the City of Worcester, unlike the other ten towns, which are all part of the first Congressional District. Leicester is the first of the eleven towns in the “frontier” section of this walk along the Upper Boston Post Road between Worcester and Springfield, but it is a transitional town with strong links to the city of Worcester both in its history and in its orientation.

The last entry in Worcester ended at the border with Leicester along Apricot Street in Worcester, which continues as Sargent Street in Leicester. The border also marks the highest elevation thus far along the roughly 51 miles of the Upper Boston Post Road that I have walked starting at the Old State House in Boston. There is some confusion about the route of the Upper Boston Post Road from Worcester into Leicester and in order to understand the history of the changing route from Worcester into Leicester I will begin by looking backward from my perch at 787 feet above sea level and heading east back down into the valley below, a valley shared between the city of Worcester and the town of Leicester, a valley through part of which passes a later version of the Upper Boston Post Road as well as the current main road west from Worcester.

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Detail from the map of Worcester produced in 1831 by Heman Stebbins showing the roads leading to the border from Worcester into Leicester (at right in this image). The “Old Road” is today called Apricot Street, as discussed in the entry Worcester #5. The road “to Albany by Springfield and Northampton” is Main Street with the exceptions discussed below. Note that in this map east is at left and west is at right. Also note that the “Old Road” climbs a steep hill while the “new road” follows the valley through which Kettle Brook (shown at top right above the “new road”) flows.

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Chapter One: Into the Valley of the Shadow of Doubt

In which the author examines and walks the various roads that may be taken from Worcester into Leicester

The first section of the walk, through an area called Cherry Valley, feels not so much as I’ve entered another town but that I’ve just continued walking through Worcester. This is in part because of the interesting topography of the town of Leicester. In the eastern section of the town closest to Worcester a number of small brooks descend from higher elevations around the road merging in the valley to form Kettle Brook, which continues east through Leicester into Worcester, eventually passing into Curtis Pond near Webster Square, as discussed in a previous entry, and ultimately joining the Blackstone River.  Topographically, the eastern part of Leicester is part of the Blackstone River watershed and is more physically connected to Worcester than to the rest of Leicester.

As I discussed above, as well as in the last of the five entries I wrote about my walk through the city of Worcester, the history of the route of the Upper Boston Post Road from Worcester into Leicester is somewhat convoluted. The original route of the road out of Worcester followed Main Street west from Webster Square to the junction with Apricot Street. Apricot Street was the oldest road west from Worcester, climbing the steep incline of Parson’s Hill to reach the border with Leicester just past South Community High School at the top of the hill, before descending the hill into Cherry Valley along what is now called Sargent Street in Leicester. I will return to this road, the original Upper Boston Post Road west from Worcester, after a brief detour back into Worcester and along a later version of the road “to Albany by Springfield and Northampton,” an initially promising candidate for the original route of the Upper Boston Post Road but one that, despite tantalizing evidence, I doubt is the original road.

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Detail of a 1939 USGS Topographical Map “Worcester South” showing the roads leading into Leicester from Worcester. The top road (splitting off from Main Street at right) is Apricot Street in Worcester which becomes Sargent Street in Leicester. Note how steeply the road climbs over Parsons Hill (called Chestnut Hill in Leicester). The lower road through the narrow valley is Main Street (Route 9). Notice a second parallel road along the middle section of Main Street around the border, which is called Great Post Road in Worcester and Locust Street in Leicester. This is likely the remnant route of the “new” road to Albany and Springfield shown on Heman Stebbins’ map of Worcester from 1831. Notice how steeply the hill rises from the road, indicating the very narrow space through which the road was built, a space likely created by the many “privileges” or dams built along the length of adjacent Kettle Brook. The various small ponds south of the road are all the product of dams across Kettle Brook. Both older and newer roads converge at the western (left) edge of the map and continue as one (with occasional deviations described in the main text) through the rest of Cherry Valley in Leicester and uphill into the center of Leicester.

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Taking Both the High Road and the Low Road(s)

The above “road to Albany” is clearly shown on Heman Stebbins’ 1831 map of Worcester, a road distinct from Apricot Street, which Stebbins labels the “Old Road.” Today the “road to Albany” or the “new road” is the continuation of Main Street after the junction with Apricot Street in Worcester. For about a third of a mile Main Street, which is also Route 9, continues through a fairly modern residential neighborhood, slowly climbing in elevation from 602 feet above sea level at the junction with Apricot Street to reach 649 feet above sea level at the intersection with Ludlow Street. The area in Worcester through which the road passes is sometimes referred to as “Valley Falls” on nineteenth-century maps but this no longer seems to be the name of the area, with some maps referring to the entire area as Webster Square, which seems to be a bit of a misnomer. Clearly at some earlier time the area was considered part of Cherry Valley, which is clearly the case for the last 0.4 miles after Ludlow Street to the border with Leicester.

It is after Ludlow Street that the “new” Upper Boston Post Road also gets more interesting, for two reasons. The first reason is that the road clearly enters what can only now be truly called a valley, with the southern edge of the road defined by a steep drop off to Kettle Brook and the northern side of the road hemmed in by the steep slope of Parson’s Hill. The road continues to climb slowly through the valley, passing a number of interesting old mill buildings along the way, part of the industrial heritage that defines much of the history of Cherry Valley, a subject to which I shall return shortly.

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The roads through Cherry Valley. At left is the current main road, formerly called Leicester Street but now Main Street, which is also Route 9, the main road west from Worcester and, for much of the way west through West Brookfield, the original route of the Upper Boston Post Road. An important exception is this stretch here, where it IS NOT the original road, since it did not exist until the late 1800s. Nor is the road at right the original route of the Upper Boston Post Road, even though it is literally called Great Post Road, a road which does not appear on maps until 1831. The original route west from Worcester passed over the hill to the north (right in the photo) of the roads shown here, along Apricot Street in Worcester and Sargent Street in Leicester. Notice that Great Post Road, the original road through Cherry Valley, is at a higher elevation than Main Street. Great Post Road becomes Locust Street in Leicester, before merging with Main Street about 800 yards west of the location above.

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The second interesting aspect of the “new” road through Cherry Valley is that it is actually made up of two roads: Main Street (Route 9), the busy thoroughfare through which most of the traffic between Worcester and Leicester passes, and a smaller, mostly abandoned road that runs parallel to the main road at a slightly higher elevation just a few yards to the north of Main Street (see photo). This vestigial tranquil road, which has no true outlet anymore and essentially peters out into the parking spaces in front of 1486 Main Street has the very interesting name of Great Post Road in the section that runs through Worcester, while in Leicester the road has the more prosaic name of Locust Street.

As the reader may imagine, this untended, little used, and nearly forgotten section of old road, with its lofty name, has long beguiled the author in his quest to discover the oldest route of the Upper Boston Post Road. The idea that perhaps this road is the original route of the Upper Boston Post Road has been ever present in my mind as I contemplated the various possible roads from Worcester into Leicester. However, despite the forlorn appeal of this ramshackle stretch of road (which is only about 0.4 miles in length if I am being generous and include the parking spaces that bisect the road a couple of times), the evidence presented in previous entries and the evidence I will present when I return to the Apricot Street/Sargent Street border where I started this entry strongly supports the idea that the route of the oldest road in this area is Apricot/Sargent Street. There is no road through the valley shown on any map of the area prior to 1831 and so Great Post Road/Locust Street is very likely the remnant of the original “new road” through Cherry Valley, the road which, by 1831 at the latest, made Apricot Street/Sargent Street superfluous. This section of the “new” road itself became superfluous as what is now Main Street/Route 9 was laid out in the late-nineteenth century and widened in the early-twentieth century to accommodate the increased traffic from automobiles while the older section of the “new” road, which ranges from 10-25 feet higher in elevation than the adjacent modern road, was left literally high and dry. Although Great Post Road, situated 710 feet above sea level at the border between Worcester and Leicester, is 15 feet higher than Main Street (695 feet above sea level at the border), it is still much lower in elevation than Apricot Street (787 feet above sea level at the border), the original route of the Upper Boston Post Road.²

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Detail from Plate 63 of the Atlas of Worcester County produced by F.W. Beers in 1870, showing Cherry Valley/ Valley Falls on the border between Worcester and Leicester. Apricot Street/Sargent Street is called “Old County Road” on this map. The modern layout of the roads through Cherry Valley had not yet been created and Great Post Road/Locust Street, called Leicester Street on this map, was still the principal road through the valley. Also note the Sargent houses at top center, the numerous factories along Kettle Brook, and the house of L.T. Upham, all discussed in this essay.

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In the course of researching this project, one of my most reliable suppositions, when presented with a choice of paths to follow, has been that the most level road is the likeliest route of the Upper Boston Post Road. Here, instead, is a rare instance where it appears that the steeper Apricot Street is actually the oldest road and that the more level and aptly-named Great Post Road is the newer road. This begs the question, why did the original route follow such a steep path when a more level path through the valley is clearly superior, particularly for transport vehicles like carts and stage coaches?³ My hypothesis is that the water level of Kettle Brook along the valley floor was originally much more substantial and seasonally variable in the eighteenth century. However, as we shall see, dams along the brook and the various streams leading into the brook were built beginning in the mid-eighteenth century which contributed to substantially altering both the flow of water and the course of Kettle Brook itself, opening up a pathway along which a road could be safely built by the end of the eighteenth century. First the one road was squeezed in and later, as technology developed, retaining walls were built to keep Kettle Brook from flooding the road (not always successfully as we shall see). Eventually the need for a wider road led to the development of the current Main Street and a large section of the old road was abandoned rather than rebuilt.

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The Last of Worcester (I mean it this time!)

*The impressive Ashworth & Jones Woolen Factory building is built over Kettle Brook.*

The distance between the point where the original route of the Upper Boston Post Road and the “new” road diverged, at Apricot and Main Street in Worcester, and the spot where the two roads rejoin in Leicester, just past Reservoir Street where Lynde Brook crosses under the road, is about 1.1 miles whichever of the two (or three, if counting the two “new” roads) routes is taken. The first 0.7 miles along either route is in the city of Worcester. I described the walk up Apricot Street in Worcester (the “Old Road”) in the previous entry. The route of the “new” road from the Apricot Street junction to just past Ludlow Street in Worcester is uninteresting. After Ludlow Street the “new” road then enters the narrow valley where, Great Post Road and modern Main Street (Route 9) run parallel to each other for another 0.4 miles to the border with Leicester.⁴ That the two roads are closely related can be gleaned from the fact that the few houses on Great Post Road are all numbered in the same sequence as the buildings directly on Main Street: in other words, the dozen or so houses along Great Post Road all have a Main Street address, despite the fact that they are not physically on what is today Main Street.

The sound of Kettle Brook running along Main Street can occasionally be heard on the rare occasion when the traffic lets up for a minute. There is one very scenic and interesting building along this section of the road in Worcester, the Ashworth & Jones Woolen Textile Factory Building, located over Kettle Brook on the south side of the road at 1511 Main Street, less than six hundred feet from the border with Leicester. This charming redbrick Victorian building with a scenic bell tower is listed on the National Register of Historic Places and was built in 1870 for Thomas Ashworth and Edward Jones. According to the Massachusetts Cultural Resources Report (MACRIS report # WOR.1430), it is “characteristic of many mills built in Worcester between ca. 1855 and the 1880s, of which few examples remain.”

*Let’s leave Worcester on a high note along the low road. Another view of the Ashworth & Jones Woolen Textile Factory, now Kettle Brook Lofts, at 1511 Main Street in Cherry Valley.*

The property has trails leading into the woods behind Kettle Brook and paths leading down to the brook which literally runs below the building and was utilized by the mill for water power. Standing on the banks of the brook as it passes under the building, it is easy to see that the road above is being propped up by a massive stone retaining wall which also supports parts of the building. It is a bucolic scene as well as a site of impressive engineering. Today the building has been renovated and houses both offices and residences under the somewhat grandiose name The Lofts at Kettle Brook Falls. A parking lot for the building and the trails behind was once the site of the impressive Queen Anne Mansion built circa 1881 for Thomas Ashworth, who died only a year after its construction. The impressive building later became a restaurant but was demolished early in this century. A photograph of the building as well the diner across the street from the restaurant (also gone) accompanies an article on the restaurant from 2014 in the Worcester Telegram & Gazette.

This turns out to be the final act of a series of destruction of the rich heritage of Worcester I have encountered as I walked more than seven miles of the route of the Upper Boston Post Road through the city.⁵ A few yards past the parking lot along Main Street I see a sign welcoming me to Leicester. Finally, I have finished writing about Worcester, for now. Unfortunately it ended on a not atypical melancholy note; despite the many interesting and exciting aspects of Worcester I encountered along the way, including the Ashworth & Jones building I just passed, there were an almost equal number of dispiriting empty spaces where an interesting building once stood, and the constant juxtaposition of these two contrasting scenarios tempered my mood as I walked through the city. I am hoping that the less densely populated towns through which the road passes for the next few miles might have managed to preserve more of the oldest artifacts along the road.

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A Dubious Milestone?

Looking east from Main Street in Leicester. At left is Locust Street, which becomes Great Post Road when it crosses into Worcester. This is likely the “new road” shown on the 1831 map of Worcester by Heman Stebbins, and the main road on the 1831 map of Leicester by an unknown author (see map below). At right is Main Street in Leicester (also Route 9), the modern route through Cherry Valley from Worcester into Leicester. Notice how Locust Street goes uphill. Milestone 52 (see below) is embedded in the retaining wall between the two roads about 20 yards past the entrance to Locust Street, to the left of the car in the photo.

A few hundred yards into Leicester and it would appear that my wish has been granted! Main Street/Route 9 in Leicester continues for about 0.4 miles west along the north side of Kettle Brook and the various ponds created by damming the brook before the road merges with Sargent Street, the original route of the Upper Boston Post Road into Leicester. Great Post Road, the old “new” road through Cherry Valley into Leicester, runs parallel to Main Street in Leicester about 40-50 feet north of and about 10-15 feet higher in elevation above Main Street for about half of the distance to the Sargent Street junction before Locust Street (as Great Post Road is called in Leicester) drops down and merges with Main Street. Along the south side (Kettle Brook side) of this part of Main Street are several interesting manufacturing buildings from the nineteenth century to which I will return shortly in my discussion of the history of Cherry Valley. Locust Street, although charming in the way these vestigial sections of the old main road often can be, does not have any buildings that I can discern of particular interest among the dozen or so houses that line the short stretch of road. That Locust Street (called Leicester Street at the time) was still the main road in 1870 is clear from a glance at plate 63 of the Worcester County Atlas of F.W. Beers (see above), which shows what is now Main Street as a side road leading to the factories on Kettle Brook. However, Triscott’s 1878 map of Worcester shows what was once the side road as the new main road, now called Leicester Street as it crosses the border, and this is certainly the case on maps from 1898 and 1910, where Main Street (Leicester Street is also still included in parentheses) has acquired its current name and form and Locust Street (no longer Leicester Street) is clearly the secondary road.

However, very close to the junction of Locust Street and Main Street, embedded in a rebuilt stone wall on the north side of Main Street is a milestone, which is great news as I have not seen a milestone for four miles, but which is also another complicating factor in my analysis of the oldest route into Leicester from Worcester. The milestone is of the red sandstone variety commonly used for the stones between Worcester and Springfield, typically sourced from quarries in the Connecticut River Valley.⁶ It reads “52 miles from Boston” although the word “Boston” is fading, as is typical of many of the stones made from this material. However, according to my calculations, this milestone is only 51.3 miles from Boston. The milestone is not included in the comprehensive Survey of Milestones (see later discussion) prepared in 1971 for inclusion on the National Register of Historic Places. If this location is not on the Upper Boston Post Road, and the distance is not correct, and the milestone was not included in the 1971 report, what is this milestone doing in this location?

This milestone is in the retaining wall on the north side of Main Street in Leicester, just east of the junction with Locust Street. According to Joe Lennerton, a local historian, it is a reproduction, as the original was lost in the 1876 Cherry valley Flood.

According to local historian Joe Lennerton, in a talk presented to the Friends of Swan Tavern, this milestone is a reproduction of the original milestone which was swept away during the Cherry Valley Flood of 1876. Lennerton states that the original was somewhere in the vicinity of the parking lot of Eller’s Restaurant, another quarter mile further west down the road. If this statement is accurate, at least the original location of the milestone would be on the actual historical route of the Upper Boston Post Road as Sargent Street rejoins Main Street almost exactly at this point. However, the milestone would still be only 51.5 miles from Boston, based on the distance I have calculated for this location from the Old State House along the Upper Boston Post Road. This stone should theoretically be located half a mile further west down the road, nearly at the place where Kettle Brook crosses under the route of the Upper Boston Post Road. Somehow, in the course of the last few miles along the road, the milestones have become misaligned and the distances represented on the stones are off by a few tenths of mile from the actual distance to the Old Statehouse in Boston along the route of the Upper Boston Post Road. Later milestones are similarly out of phase (all are between a half mile and three quarters of a mile out of phase and always a bit short of the actual distance rather than too far away) with the actual distance along the road as we shall see. The last milestone before Worcester along the road was milestone 43 in Shrewsbury which has recently been moved. The original location of the milestone in Shrewsbury was almost exactly 43 miles along the road, so that milestone corresponded well with my calculations. Milestone 47 in Worcester, like milestone 52 in Leicester was similarly misaligned, likely deliberately moved, as milestone 48 certainly was (it is not located on the route of the Upper Boston Post Road at all). These are the three most recent milestones I have encountered since passing milestone 43, so something has clearly changed in the interim. This is a mystery that I will return to as I gather more information along the road.

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Back To The Starting Line

*View west down Sargent Street into Cherry Valley.*

Sargent Street heads east uphill from the putative former location of milestone 52 in front of Eller’s Restaurant. From this spot it is 0.4 miles to my original starting point at the top of the hill on the border between Worcester and Leicester. Apricot Street in Worcester, the route of the original road west into Leicester, climbs steeply to the border at which point the road is 787 feet above sea level, the highest point thus far along the first 51 miles of the Upper Boston Post Road.

So, after a long detour along the low road, I return to my starting point and begin the official walk along the Upper Boston Post Road in the town of Leicester. As I enter Leicester and begin the 52nd mile of the walk from the Old State House in Boston, the sidewalk ends at the Worcester line and the road continues uphill for a few more yards before peaking at 791 feet above sea level (a new high elevation) after which it levels off for a hundred yards. The walk along quiet Sargent Street is pleasant, particularly as the road begins to descend in a sweeping curve back down into Cherry Valley, providing a lovely view west overlooking the valley.

Most of the property along the road was owned in the eighteenth and nineteenth century by the Sargent family, hence the name of the road. Nathan Sargent (1718-1799) arrived from Malden in 1742 and settled on Chestnut Hill, the name given to this elevated area in Leicester (which is sometimes called Parson’s Hill over the border in Worcester). Further evidence that Sargent Street was the old road between Leicester and Worcester is supplied by two or three anecdotes in Emory Washburn’s Historical Sketches of the Town of Leicester during the first Century from its Settlement (1860).⁷ Washburn discusses the changes in the route of what he refers to as the Country Road which “formerly passed from New Worcester, over the summit of the hill, and near to the dwelling-house of Mr. John Sargent,” John Sargent (1759-1829) being the son of Nathan Sargent.⁸ In 1855 John Sargent’s house was occupied by his son Sewall, labeled as the house of “S. Sargent ” on the map of Leicester produced by E.M. Woodford. The house of “S. Sargent” is also shown on the 1870 Atlas of Worcester County by F.W. Beer (Plate 63) on the north side of what is now Sargent Street, directly opposite what is today Woodworth Street, about 250 yards from the border with Worcester. Today Redfield Street passes directly through the property and it appears the house is no longer extant.⁹

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This unassuming house at #92-94 Sargent Street in Leicester may be the house built in 1742 by Nathan Sargent, one of the earliest settlers in Cherry Valley. The original route of the Upper Boston Post Road passed along Sargent Street over Chestnut Hill until a road through the valley was built in the early nineteenth century.

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A book I found in the Leicester Public Library called Where the Wild Strawberries Grow: A Pictorial History of Leicester (1997) by Dale Pitzen and Mary Kennedy claims that the house located on the northwest corner of Sargent and Redfield Streets, currently #92-94 Sargent Street, is the original Nathan Sargent house.¹⁰ Although the number and location of the windows and the general structure of the current house is similar to old photos of the Sargent house, the building has been modernized over time and is easy to overlook (see the photo above–I certainly did not notice it the first time walking past). There is no MACRIS record for the building which one would expect for a building of such age. However, it is undeniable that the old photos of the house definitely correspond to the structure of the current building. Although this particular house is not the most aesthetically pleasing I have encountered along the route of the Upper Boston Post Road, it is still exciting to find a building that is close to three hundred years old along the road.

Washburn describes the departure of the Leicester company of minute-men organized to march to Cambridge after the Battle of Lexington and Concord in the spring of 1775: “In this company of minute-men was a son of Nathan Sargent, who lived near the line of Worcester where Mr. Sewall Sargent now lives. As the company came up they halted in front of his house. Mr. Sargent came out to greet them, and inquired of the captain if they were supplied with ammunition. On hearing that there was a deficiency in bullets, he went back into the house, took from his clock the leaden weights that carried it, and, melting them down, cast them into bullets, which he brought out and distributed to the men.”¹¹ This fanciful tale (honestly, how long did they have to sit around waiting for him to heat the furnace to melt down the lead for example?) is accompanied by another about a certain Luke Day, a member of the insurrectionary forces led by Daniel Shays; in 1787, “(Day) had occasion to pass from Worcester, through Leicester, on his way to Springfield….Upon reaching the house of Nathan Sargent, the first one in Leicester on his way from Worcester, he stopped, dismounted, fastened his horse, and went into the house to warm him(self).”¹² I will cut to the chase and tell you that Nathan Sargent did not approve of the rebellion and threw him out. The main point of these two anecdotes is to provide more evidence that Sargent Street, at least as late as 1787, was the main road from Worcester, through Leicester, to Springfield.

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Plate 24 from The Worcester County Atlas of 1898, published by L.J. Richards and the Publisher’s Corp of Civil Engineers. This is a detailed map of Cherry Valley from the border with Worcester to the point where Main Street crosses Kettle Brook and begins the climb into Leicester center. Note at right the “three roads” into Leicester from Worcester, the one at the top being the original route of the Upper Boston Post Road. All three roads merge into one road just before crossing Lynde Brook (after Reservoir Street). The 1876 Cherry Valley Flood occurred when the reservoir above Lynde Brook gave way, leading to massive destruction of most of the buildings east of the brook almost as far as Webster Square in Worcester. Also note that the configuration of Main Street near Kettle Brook at left has been significantly altered (compare with the modern map at the end of the entry). Finally, notice the house owned by Homer Sargent just north of the junction of Main Street and Sargent Street, as well as “Valley Woolen Mills, east of what is now Smiths Pond, among other features discussed in the main text.

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According to Amos H. Coolidge, in his Brief History of Leicester, Massachusetts (1890), the name Cherry Valley was given to the area by Reverend Benjamin Conklin, minister of the town from 1763-1794: “Although the eastern village of the town does not appear to have been commonly called Cherry Valley till nearly the end of the first quarter of the present century, the name was given to it in the last century, as we learn from the manuscripts of Miss Anna Henshaw, written in 1846, and containing materials of special value to local geneologists (sic) and historians: “Asa Sargent m. Charlotte Earle and resides in Cherry Valley, Leicester. ‘Cherry Valley’ is a name given to that locality by the late Rev. Mr. Conklin (of pleasant memory) after Cherry Valley on Long Island, New York. Mr. Conklin considered it at that time the ‘pleasantest place in Leicester.’ Anna Henshaw was born in 1778, and was therefore a contemporary of Rev. Benjamin Conklin, who died in 1798.” Conklin was born on Long Island.¹³

Asa Sargent (1784-1854) also lived along Sargent Street nearly at the junction with Main Street and his house is shown on an 1855 map of Leicester produced by E.M. Woodford. A little further east along Sargent Street is the house discussed above of Nathan Sargent, shown on the map as belonging to Sewell Sargent (1799-1894), brother of Asa Sargent, and grandson of Nathan Sargent. The Asa Sargent house also appears on Plate 63 of F.W. Beers Atlas of Worcester County published in 1870, where it is listed as belonging to H. Sargent and it appears on Plate 24 (Cherry Valley Leicester) of the Atlas of Worcester County published in 1898, owned by Homer Sargent, son of Asa Sargent.¹⁴ The sole house along the road down from the border with Worcester that attracts the eye is the white house with a red star on the facade at 18 Sargent Street (see photo). There are numerous buildings on the property, including what appears to be a barn. The shape, orientation, and location of the house itself appears to be the same as the house shown on Plate 22 of the 1898 Atlas, Plate 63 of the 1870 Atlas, and on the 1855 Woodford map, and a house with the same shape at the same location appears on the 1910 Sanborn Insurance map (plate 12) of Leicester. There is no listing in the Massachusetts Cultural Resource Information System (MACRIS) website, part of the Massachusetts Historical Commission under the purview of the Massachusetts Secretary of State, one of the most valuable resources I have utilized for this project. Nonetheless, the house at 18 Sargent Street likely dates to at least 1855 and is in all likelihood the house shown on the maps I have described owned by multiple generations of the Sargent family, one of the earliest families to settle in what became Leicester. The Sargent House is the last house on Sargent Street and overlooks Cherry Valley and the small square that sits at the junction of Sargent Street, Main Street, and Reservoir Street. From this point Main Street and the Upper Boston Post Road continue as one through Cherry Valley and the circle of roads leading between Leicester and Worcester has been closed.

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Chapter Two: Flooding The Transition Zone

In which the author walks through Cherry Valley in Leicester.

A sign in Cherry Valley, Leicester, Massachusetts. The 1743 date shown is the year Nathan Sargent likely established a grist mill on Kettle Brook, the first of many mills in the valley, peaking in 1889, when there were more than ten factories operating here.

From the junction of Sargent Street and Main Street in Leicester, the route of the Upper Boston Post Road, Main Street, and Route 9 are mostly one and the same through Leicester, Spencer, and most of the town of East Brookfield, with the old road taking the occasional, always interesting, deviation from the main road. The first part of the walk along this fairly busy road passes through the relatively flat Cherry Valley, an area that I have previously mentioned has stronger cultural, political, demographic, economic, and geographic ties to Worcester than the remaining towns and neighborhoods along the Post Road to Springfield. Effectively this first mile or so along the road is a transitional walk taking us to the edge of the Blackstone River watershed and slowly weakening the links to Worcester and to Greater Boston.

The town of Leicester is comprised of three separate watershed systems. The majority of the town is part of the French River watershed which drains south and ultimately becomes part of the larger Thames River watershed in Connecticut, which drains into Long Island Sound at New London. The northwestern section of town is part of the Quaboag River watershed, as are all the remaining towns along the route until the road passes into Springfield. Once the road begins to rise out of Cherry Valley, it enters an area which is quite high in elevation relative to any other part of the road that I have traveled thus far and the landscape itself feels distinctly different. Essentially Cherry Valley is the transition zone between the heavily populated city of Worcester, part of the Blackstone River Valley watershed, and the lightly populated countryside beyond, most of which is part of the Quaboag River watershed which ultimately drains into the Connecticut River. The road beyond Leicester “faces” west while in Cherry Valley it still “faces” east.¹⁵

The small brook over which Main Street passes just beyond the intersection with Sargent Street provided a dramatic example in 1876 of the “east-facing” character of Cherry Valley. Lynde Brook descends from the hill immediately to the north of the Upper Boston Post Road, at the top of which was built a reservoir in the nineteenth century which provided water for the City of Worcester. The dramatic story of the events which took place in the spring of 1876 is told by Amos Coolidge in his Brief History of Leicester: “On March 29, 1876 the dam of Lynde Brook Reservoir… gave signs of weakness…on Thursday March 30, a little stream of water broke out above the lower gatehouse. The alarm was given…the bank of the dam caved in…and the reservoir poured its contents into the channel below. The scene is described by many who witnessed it as grand beyond description…The water, nearly fifty feet in height, came surging, seething, rolling on..when it reached the street it tore away the bridge and road-way and then spread out over the meadow, converting the lower parts of the village into a sea, and then at Smith’s dam was forced through the narrow passage…the flood tore away most of Smith’s factory, annihilated Bottomly’s mill and carried away the rear of the several factories along the stream and the dams…Several tenement houses were destroyed…it wrenched away the boiler of Ashworth and Jones’ mill and deposited it half a mile below.”¹⁶

Albert Southwick, longtime journalist for the Worcester Telegram and Gazette, Leicester resident, and a historian of the town and of Worcester County, describes the carnage reaching deep into the City of Worcester in his Once Told Tales of Worcester County : “The surface of the 700 million gallon reservoir is 824 feet above sea level, 120 feet above Main Street in Cherry Valley…the 400 yard wide river in the valley poured into Smith’s Pond destroying the 200-foot dam… two buildings at Ashworth and Jones factory were destroyed… the water then savaged the tracks of the Boston & Albany Railroad… eventually flooded Curtis Pond and then destroyed the bridge on Webster Street as well as flooding Curtis Street and Leicester Street…Curtis Pond dam fell, Curtis and Marble mill was destroyed and Webster Square was flooded…damage was estimated at one million dollars which was $50 million in 1984 (when the story was published and probably hundreds of millions of dollars today) but only one or two people seem to have drowned, as most had been removed to safety well before the dam broke.”¹⁷

The dramatic story of the Flood of 1876 retains its ability to astonish and interest locals as well as the occasional stranger passing through town along the Upper Boston Post Road. Joe Lennerton, a local historian of Leicester, recently gave an excellent presentation about the flood which can be found on the Facebook page of the Swan Tavern. In addition to exploring the causes, events, and aftermath of the flood, he notes that, despite the massive damage evident in the dramatic images he presented of the aftermath of the flood, miraculously nobody was killed. Lennerton’s presentation is much more interesting and detailed than the brief summary I have presented as I wander through Leicester along the route of the Upper Boston Post Road, and is well worth an hour of the reader’s time. One of the main purposes of this project is to try to contextualize larger historical patterns within the framework of events as they have been interpreted and understood at the local level. Lennerton’s discussion of the political struggle of the small town of Leicester against the more powerful forces of the burgeoning city of Worcester next door over control of the land and water in the town of Leicester and the resulting impact on the town is one of countless stories along the route of the Upper Boston Post Road that are interesting not only within the context of “local history” but also can be analyzed within the larger historical framework, in this case the industrial and economic development of nineteenth-century America.

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Milling Around

Facade of Smith’s Mill building, which was rebuilt after being almost completely destroyed by the Cherry Valley Flood of 1876. The section of the building shown here was added in 1918, as can be gleaned from the inscription.

More evidence that Cherry Valley was in many ways a continuation of Worcester is the presence of a number of old mill buildings along the road through the valley just as we have seen along the road through Worcester. Almost immediately after entering Leicester along Main Street is the large redbrick complex which once housed Smith Mills, the name still engraved in the building (see photo at left). This property was one of the most dramatic casualties of the 1876 flood as related above. The first person to build a factory at this location was Thomas Bottomly in 1836 on the privilege along Kettle Brook early occupied by Nathan Sargent, who operated a grist-mill here in the eighteenth century.¹⁸ According to Amos Coolidge “Mr. Bottomly may truthfully be termed the founder of Cherry Valley as a manufacturing village. When he came to Leicester there were, as nearly as can be ascertained, only ten houses in what is now the village. Most of the present residences were built in his lifetime, and it was by him that the three brick factories were erected.”¹⁹ On Peter Silvester’s 1795 map of Leicester (see below) a “corn mill” is shown along Kettle Brook in the vicinity of the present Smith Mill buildings, and a “grist mill” is marked on an 1831 map of Leicester at the eastern edge of what is now Smiths Pond. Bottomly began the manufacture of broadcloth (a type of wool cloth) on the site in 1837. Over the years a succession of different owners operated the mill, including James Smith who bought the vacant privilege in 1865. The buildings were rebuilt after the 1876 flood, and the mill eventually operated as “Valley Woolen-Mills” and can be seen on the map above from 1898, immediately east of Smiths Pond on the south side of Main Street. Today the building, like almost all the remaining mill buildings, houses a variety of businesses, including an antique store and a fitness center.

The property immediately west of the Smith Mill building complex is shown on the 1898 map of Leicester above as the property of “Mrs. A.E. Smith,” the widow of a later owner of the Smith Mills. The house at #119 Main Street, a rare residential property along this busy section of Main Street corresponds in location and shape to the first of the two houses shown on the map, particularly as there is a corresponding second garage/barn-like structure behind it overlooking Smiths Pond, just as there is today. The presence of a very large European Beech tree in front of the house close to the road is further evidence that the current property likely dates to the nineteenth century. St. Thomas Episcopal Church, the next property west along the road shown on the 1898 map, was built in 1884 and consecrated in 1885, but is no longer found at the site, which is today occupied by a large parking lot fronting Smiths Pond.²⁰ DeSouza’s Catch, a food truck located in the parking lot, is operated by a friendly Brazilian named Fabio offering generous portions of fried seafood along with a few tables and chairs overlooking Smiths Pond. I take a break from walking the various routes from Worcester into Leicester and enjoy a plate of fried clams as I ponder the history of Smiths Pond, formed by a dam on Kettle Brook, one of many ponds along the relatively short route of the brook (which forms in the neighboring town of Paxton) created by dams built on “privileges,” the right to use the water as a source of power at specific locations.²¹

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The Upper Boston Post Road through Leicester in 1855. This is a detail from a map produced by E.M. Woodford, showing what is today Main Street for the most part in Leicester. Notice the densely built Cherry Valley area in the east of town near Worcester. Also notice the number of ponds created by dams across Kettle Brook, which were used to power the numerous factories that developed in the valley in the nineteenth century.

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Fulling Around

Monument “Erected by the citizens of Cherry Valley in honor of their soldiers, sailors, marines, and nurses who served or died in the World War.” This monument sits in the triangle formed by Reservoir Road, Sargent Street, and Main Street in Cherry Valley, and serves to indicate that the area has long been considered a place of its own within the town of Leicester.

After my lunch break I need to walk off Fabio’s fried clams, so I continue west along Main Street, past the American Legion building, built on one of many former properties of another Leicester manufacturer and businessman, George Olney, before I cross over the diminutive Lynde Brook again and return to the junction of Sargent Street and Main Street, where Main Street/Route 9 becomes the route of the Upper Boston Post Road west into Leicester. It is hard to believe this small brook, which is barely noticeable as I walk over it and is unlikely to be noticed by a person driving along Route 9, was the source of such catastrophic damage to most of the area through which I have just walked. It is also hard to reconcile the fact that the relatively small and tranquil town of Leicester was an early and important manufacturing center, and yet both statements are true.

A concentration of what appear to be modest nineteenth-century working-class houses along Main Street is a legacy of the industrial enterprises that once dominated Cherry Valley. E.M. Woodford’s map of Leicester from 1855 clearly shows that Cherry Valley, along with Leicester Center, were the two main population centers of the mid-nineteenth century town as evidenced by the density and number of buildings shown on the map in these areas relative to other parts of town.²² There are dozens of properties shown on Woodford’s map along the quarter of a mile of Main Street from Lynde Brook to a little past today’s Church Street. There are about two dozen more structures shown on the map along the road continuing to Collier’s Corner and then only a handful of buildings along the next three quarters of a mile of Main Street/Upper Boston Post Road west to Mannville Street, before the road heads steeply uphill into Leicester Village, and the density of buildings increases again. Immediately beyond Lynde Brook on the south side of Main Street the words “Boarding-Houses” are prominently displayed near a cluster of buildings on Woodford’s 1855 map, consistent with the architecture of some of the buildings I pass on Main Street as I continue to walk west from Lynde Brook along the 52nd mile of the route of the Upper Boston Post Road from the Old State House in Boston.

The development of manufacturing in Cherry Valley dates to the earliest days of settlement. An earlier map of Leicester from 1831 shows not just a “grist mill” along Kettle Brook but also a “saw mill” and two “woolen factory” buildings. Even the 1795 map of Peter Silvester Jr. shows what appears to be the same saw mill as well as a “fulling mill” in what appears to be the site of one of the woolen factory buildings from the 1831 map.²³ On the 1870 map of Cherry Valley there are a minimum of four woolen factories shown and at least as many on the 1898 map. According to Coolidge “there are in 1889 ten woolen-mills in the town of Leicester, and nine firms engaged in the manufacture of woolen cloth.”²⁴ Today there are no extant woolen mills in Leicester as far as I have been able to ascertain.

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Detail of a map of Leicester produced in 1831 by an unknown author showing Cherry Valley from the Worcester border (at right) to “Collier’s Corner” just beyond the bridge over Kettle Brook along Main Street. Notice the presence of various mills and factories from the “Grist Mill” at right, where the Smith Mill Buildings are now located, a “Saw Mill,” and two locations labelled “Woolen Factory.” The Woolen Factory at far left, south of Main Street along Kettle Brook on what is today Auburn Street, is the likely site of the “fulling mill” purchased by Alexander Parkman in 1770. Notice also that Sargent Street was no longer the main road to Worcester at right and that what is now Locust Street, which passes through Cherry Valley, was shown as the principal road to Worcester on the map.

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Cherry-picking

The use of water as a source of power in almost every town along the route of the Upper Boston Post Road is a familiar topic in this project. Cherry Valley in Leicester offers a particularly clear illustration of the progression from early simple corn mills, such as the one established by Nathan Sargent, to the numerous large factories using steam power operated by Thomas Bottomly, George Olney, Samuel Watson, and many other names that appear in the annals of nineteenth-century Leicester. As this is a record of the road and not a history of manufacturing in Leicester, the history of one specific site along the route will serve here as an example for all the various mills and factories along Kettle Brook and elsewhere in Leicester. As Coolidge states in his History of Leicester : “Samuel Watson is entitled to the position of pioneer woolen manufacturer in Leicester. During the War of 1812 he… began the weaving of woolen cloth upon looms moved by hand. The mill was located on the Auburn Road near Main Street, on the privilege used by Richard Southgate for his saw-mill, the second erected in town. Alexander Parkman afterwards used it as a fulling-mill.”²⁵

There is a lot to dissect in these few short sentences which carry us through more than a century of history and also connect the story directly to the Upper Boston Post Road as Alexander Parkman is the son of Ebeneezer Parkman, longtime minister for the town of Westborough. Ebeneezer Parkman kept a diary, spanning many decades (1723-1782), of his activities and observations including a record of the many visits he made to his son Alexander and the story of his business venture in Leicester. Thus, a travel narrative I have used in many previous entries, which has provided us with vivid descriptions of the eighteenth-century version of the Upper Boston Post Road, also in this instance affords a personal glimpse of Cherry Valley on the cusp of the industrial revolution which transformed the character of the area.

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Detail of 1795 map of Leicester by Peter Silvester Jr. showing what is now Cherry Valley. In this map the view is looking from north (bottom) to south (top) with the border with Worcester at left (east). Kettle Brook is the dark wavy line that crosses the red line representing “The Country Road from Boston to Springfield” before turning east (left) into Worcester. Notice the three mills along Kettle Brook: a corn mill, a saw mill, and the “Fuling mill” purchased in 1770 by Alexander Parkman.

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Peter Silvester Jr. produced the official map of Leicester for the Commonwealth of Massachusetts in 1795. Clearly labelled on the map (see above) on the south side of the road along Kettle Brook, a little east of where the brook takes a sharp turn north and crosses the Upper Boston Post Road, is a “Fuling mill.” The first mention in the diary of Ebeneezer Parkman of Alexander Parkman’s plan is on February 7, 1770, when he states “my son Alexander acquaints me with his Desire to throw up at Sturbridge and buy at Leicester, and settle there.” Five days later Reverend Parkman reports “My son Alexander wants I should go with him to Leicester to be bound for him if he buys the House, Mill, etc which one Ebeneezer Crossman, clothier, lately occupied there.” The next day Parkman reported “there came to me the Three Partners in the Interest which my son wants to purchase, viz. Captain John Brown, Mr. Matthew Watson (with whom was Thomas Denny) and Mr. John Southgate…the afternoon is spent with the Partners settling of their Accounts and agreeing with Mr. Watson about the Privilege of the Dam and Pond. On February 14, 1770 Parkman notes that “After breakfast we came to Messrs. Southgate’s; we went thence and viewed the works at the Place, the House, the Mill, the Dam, the Stream, and had a list of tools–and they were delivered to Alexander. Then we went to Mr. Watson’s, where his wife Signed the Deed (as he had done last night) and then the witnesses signed. Then Alex and I signed the notes for payment of the money.” By May 24, 1770, Parkman writes that “Alexander and his wife and Child were gone to Leicester.”

According to Emory Washburn, in his Historical Sketches of Leicester, “the first clothier in town, I have reason to believe, was Alexander Parkman, who came from Westborough in 1770…he purchased the mill and privilege where Samuel Watson afterwards carried on business, in Cherry Valley. He carried on the business till after 1776.”²⁶ Washburn also states later that Parkman “lived in the house lately occupied by Rufus Upham, which he bought of the Southgates in 1771.”²⁷ Watson’s factory burned in 1848 but Watson properties can be seen along the south side of Main Street near Auburn Street shown on Woodfords map of 1855.²⁸ The house of “R. Upham” is also visible on the map on the north side of Main Street a few yards west of the junction with Auburn Street.

Alexander Parkman appeared to have had a streak of misfortune during his time in Leicester. While purchasing the mill in Leicester with his father, his store in Sturbridge was broken into and “30 yards of cloth stolen” by a thief who absconded over the border into Connecticut, as recorded in his father’s diary (March 19, 1770). Shortly after Alexander settled in Leicester, Ebeneezer Parkman reported in his diary (September 14, 1770) that “just after Midnight, in rain and very dark came Mr. Thomas Earl from Leicester, with the sorrowful message that my sons child was dead…At about 11 a.m. I sat out in the rain with Mr. Earl…Arrived before Night at my son Alexander full of sorrow. The Child was nigh eighteen months old…The Neighbours there were very compassionate–especially Dr. Robert Southgate. I lodged at my Sons.” Parkman’s diary recorded over the next few years numerous instances of his son’s financial difficulties and many bouts with illness and poor health endured by Alexander and his wife Kezia, not to mention a cryptic comment on November 6, 1771, about his son Alexander’s “disappointment in having rollin fullin works.”

By 1776 Alexander had joined the army and was sent to New York. In 1777 he was back in Leicester but was scheduled to march to Bennington, Vermont. Parkman’s entry for January 7, 1778 reports that “After dinner, Alexander has my Oxen to Godfrys that they may be shod, and that he may take them with him to Leicester, in order to his having them in his Journey to No. 5, or Marlborough in New Hampshire.” An entry from March 7, 1778 reports “Alexander Came at Midnight from Marlborough in New Hampshire, where his Family now is, and has also driven home my Oxen. After dining with us, he returns by way of Leicester.” Thus ends the story of Alexander Parkman in Cherry Valley, at least in Leicester, Massachusetts. Parkman built a fulling mill in the area of Marlborough, New Hampshire that is now the town of Troy and was an important figure in the town before moving to Cherry Valley, New York in 1788.²⁹ The peripatetic Alexander Parkman died in 1828 and is buried in Westmoreland, New York, 45 miles west of Cherry Valley, New York, and 219 miles west of his one-time home in Cherry Valley in Leicester.

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Moving Through the Valley

*286 Main Street, Leicester, Massachusetts.*

I need to become more peripatetic if I am ever to get through the town of Leicester, so I will try to make my way through the rest of Cherry Valley in a less languorous manner. A couple of minutes walk west of Lynde Brook on the south side of Main Street (#231) is a somewhat disheveled church which today offers services led by Christ Vision Ministries, a branch of a Liberian Church, although Google Maps until recently listed the building as belonging to a messianic group called Melech Yisrael Congregation. The building began as a Methodist Episcopalian Church founded in 1842 in the center of town and relocated here in 1846.³⁰ The current building was erected in 1856 after the first building burned down. The building, located at the southeast corner of Main Street and Church Street, is visible in Woodford’s 1855 map, as well as on Beers’s 1870 map of Cherry Valley, the 1898 Worcester Atlas map, and the 1910 Sanborn Insurance map (Plate 12), consistently referred to as the “ME Church.” The building was renovated and moved further back from the road in 1901 but by 1996 the church was no longer occupied by the Methodists.³¹

The house at 238 Main Street, appears to be an old house but I can find little information about it in the local history books. On older maps the building appears to be owned by George Olney, who also had a mill located a little west of Church Street, in the same location as the Woolen factory shown on the 1831 map of the area. Today there is only a park located where a large factory once stood, adjacent to the Cherry Valley Cemetery, opened in 1816, where Smiths, Sargents, Olneys and other familiar Cherry Valley names are buried.³² Also gone is the pond formed by the dam on Kettle Brook at the location, the brook having been restored to some semblance of its original state.³³ West of Church Street, the restored Kettle Brook runs quite close to the south side of Main Street for a few hundred yards and so the south side of the street today is tree-lined and undeveloped along that short uphill stretch. Opposite the church is a a sculpture of a lion with a sign indicating the small green space behind is Lion’s Park. The handful of houses along this section of the road are a mix of pleasant late-nineteenth century cottages and less interesting modern houses, some occupied by small businesses. A decaying house at 286 Main Street at least looks old and possibly interesting but it has the look of a building soon to be torn down.

Four hundred yards west of Church Street is the intersection with Auburn Street. I walk a few yards south along Auburn Street before the road crosses over Kettle Brook. Like the Bottomly/Hodges/Olney Mill site off Church Street, there is little evidence of any of the saw mills or fulling mills or woolen factories that operated here for more than a century. Retracing my steps to Main Street I pass a run-down building at 385 Main Street, at the southeast corner of Main Street and Auburn Street, housing Sunrise Discount Liquors. The map of 1898 shows the property as yet another along the road owned by George Olney, while the Sanborn Insurance map from 1910 for the area (map #10) shows a building labelled “Tenements” at the location, which looks about right for the sad-looking structure before me. Just beyond Auburn Street is the first deviation of the original route of the Upper Boston Post Road from Route 9, as the old road curves away to the north while the current road continues straight ahead for 300 yards before the two roads merge again. On Woodford’s 1855 map of the area, only four properties are shown from the Auburn Street intersection to the bridge over Kettle Brook. The first one is Watson’s store on the south side of Main Street at Auburn Street near to where Parkman’s fulling-mill and Southgate’s saw-mill were located and where the Sunrise Liquors is currently located. There are two houses belonging to H.M. Burr on the north side of Main Street at the Auburn Street junction, followed next west by the property of “R. Upham,” already mentioned as the house purchased by Alexander Parkman. Finally, a complex of buildings owned by “Dickinson” is shown just past what is today Chapel Street, next to yet another mill pond created by a dam across Kettle Brook.

Washburn states that Thomas Earle, the neighbor of Alexander Parkman, who arrived in the middle of the night in Westborough and informed Ebeneezer Parkman of the death of his grandson, “resided in Cherry Valley, in the house where Mr. Heman Burr lives. He planted the fine rows of sycamores that stood in front of it, on the day of the battle of Lexington.”³⁴ The 1870 map shows the once large property divided into four smaller properties, which appear to be the same ones shown on the 1898 map of the area. Although the property had been subdivided and developed, Coolidge claimed in 1890 that “three (of the sycamore trees) are still standing.”³⁵ Today it is difficult to discern the large trunks of any sycamore trees in the dense tangle of overgrowth separating the houses from the road, so I suspect the trees have long disappeared from the scene.

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The house at right, 414-416 Main Street, is the house purchased in 1770 by Alexander Parkman from the Southgate’s, a prominent family in Cherry Valley. The house was later owned by the Upham family and can be seen on maps of 1855, 1870, and 1898 shown in this entry.

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Following Three Centuries of Footsteps

The houses on the north side of Main Street (#414-416 and #420) just after the split with Route 9, are both located on the property shown on the 1898 map as the Lyman Upham estate and on the 1870 map as the property of “L.T. Upham,” in the same location as the “R. Upham” property on Woodford’s map of 1855; Lyman Upham (b. 1820) was the eldest son of Rufus Upham (b. 1789-d. 1857).³⁶ The modern road layout appears to have been built in the 1920s or 1930s, as maps from 1918 do not show the modern road, but U.S.G.S. topographical maps of Leicester from 1937 onward show the new straight section bypassing these houses. However, that this vestigial section was part of the original road is clear from earlier maps and from Emory Washburn, who includes in the Appendix of his Historical Sketches of the Town of Leicester a description from the town records of the layout of what he refers to as the “Country Road from Worcester to Spencer,” dated October 5, 1723: “From Chestnut Hill to the Meeting-House shall be four rods in breadth, as it is now marked on both sides of the way; with and under this alteration–that this part of the aforesaid road below Mr. Denny’s house, towards the brook, shall be measured from the fence on the south side of his house, four rods wide, all along southward of said fence until it comes to the brook at the bridge; and then the road is to run as marked out from that bridge, all along to Richard Southgate’s, of the above-mentioned width, and Daniel Denny is to alter his fence where it encroaches thereupon.”³⁷

Chestnut Hill, the reader may recall, is the hill upon which Nathan Sargent built his house and over which Sargent Street passes, the original route of the Upper Boston Post Road. A rod is 16.5 feet in length, thus four rods is 66 feet wide. Washburn explains that “the house referred to in the above, as then standing, Daniel Denny’s, (is) where Rufus Upham lately lived…”³⁸ As I discussed above, Rufus Upham died in 1857 and Washburn published his book in 1860. The town records order Denny to alter his fence where it encroaches upon the road, implying that his property was adjacent to the road. It also notes that the road runs along the south side of the house, which puts the house on the north side of the road where the Upham property is located. Putting all the pieces together, this is evidence that this section of Main Street, running along the south side of the property which is likely the former home of the Upham family, the house which Alexander Parkman purchased from the Southgate’s and in which he lived during his time in Leicester, and before that the property of Daniel Denny, dates to at least as far back as 1723. In other words, the road here has been traveled for over 300 years.

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*Chapel Mills, 424 Main Street, Leicester.*

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Immediately beyond the former Upham estate, just before reaching Chapel Street, is a collection of industrial buildings called Chapel Mills, now housing a company called Wood Art Exhibit Group. Some of the buildings are likely the same ones that appear on the 1910 Sanborn Insurance map (#9) as “Chapel Mills MFG. Co.” On the 1898 map the buildings on both sides of Chapel Street are the “Charles Bigelow Satinet Factory,” while on the 1870 map the buildings are shown as “Dickinson Heirs Woolen Mill.” Woodford shows the building as “Dickinson” on his 1855 map. Coolidge states that “about the year 1835, L.G. Dickinson built the embankment north of Main Street and the dam south of the road, where Collier’s Mill stands. This mill of Mr. Dickinson was used as a saw-mill until 1844, when it was converted to a satinet factory.”³⁹ Satinet, incidentally, is a finely woven fabric, often made of wool, and Cherry Valley had a number of factories dedicated to the production of satinet. Dickinson then leased that property and purchased the mill across the road in 1854. This mill burned in 1865 and was “rebuilt from the lumber of the old baptist church in Greenville, thus giving to the mill the name of Chapel Mill.”⁴⁰ Dickinson died in 1870 and is buried in Pine Grove Cemetery in Leicester.

After Chapel Street the new configuration of Main Street curves to the south and rejoins Route 9. However, like a palimpsest, traces of the old road are still visible. A very short segment of Main Street continues for less than fifty yards straight past the curve until the old road ends abruptly at Kettle Brook. There is no bridge over the stream, so I follow the new road across Kettle Brook. On the west side of the brook the faintest trace of the old road can be seen crossing the property of Mac’s Auto Repair on the north side of the new version of Main Street at a junction with Willow Hill Road that is sometimes called “Collier’s Corner.” This is a reference to the “Satinet Factory” operated by Eli Collier on the site of the the property developed by Loyal G. Dickinson in the 1830s. The Eli Collier Satinet Factory is shown on the 1898 map of the area on the south side of Main Street straddling Kettle Brook (see Plate 24 above, the first map, at far left). On the 1870 map it is labelled “Eli Collier Woolen Mills (Oc. for ‘occupant’) Dickinson Heirs (Ow. for ‘owner’),” while on Woodford’s 1855 map it is referred to as “L.G. Dickinson’s Woolen Mill.” The area called Collier’s Corner is an old junction that appears on the 1831 map of Leicester (see above) where Willow Hill Road (technically Cross Street for a few yards) heads southwest for 0.4 miles before ending at Henshaw Street, another old road leading into Leicester Center from the south. At Collier’s Corner, Main Street takes a sharp turn to the northwest directly below the house at 500 Main Street, a house built in 1846 which can be seen on the 1855 map, owned by D. Morton, and on the 1870 and the 1898 maps as the Eli Collier residence.⁴¹From here the road begins a steep ascent uphill into the center of Leicester, leaving Cherry Valley and transitioning out of the Blackstone River watershed. Although this has long been the path of the Upper Boston Post Road up the hill, there may have been an even older route through Collier’s Corner and up the hill that diverged slightly from the road travelers have followed for the last two centuries.

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The old road meets the new road. Main Street deviates from Route 9 for 300 yards at Auburn Street. Here the old road curves south to rejoin Route 9 (where the white truck is located). Prior to the 1930s, the original road once continued straight, the vestigial remains of the road still clearly visible in the photograph as the road abruptly ends at Kettle Brook. An even earlier version of the road may have followed the curve, crossed Kettle Brook on the other side of Route 9, and continued along Willow Hill Road as discussed below.

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Chapter Three: Stepping It Up.

In which the author climbs the hill into Leicester Center and exits the Blackstone River watershed.

At Collier’s Corner I encounter another milestone embedded in the embankment wall on the north side of Main Street just past Collier Avenue (510 Main Street). This stone is similar to the previous stone in that it seems to be made of sandstone. It also has suspiciously crisp engraving and the number “53” and the words “Mile from Boston” are very clear and easy to read. A survey of the “1767 Milestones” was prepared in 1971 for the National Historic Register (available on MACRIS; milestone 53 is listed as entry LEI.911, where the PDF for the entire milestone survey can be downloaded) in which this milestone is briefly described. The location is the same as it was in 1971, “Route 9 at Collier’s Corner,” although the surface of the wall has been redone. The stone itself looks the same, with only a small amount of wear on the stone compared with the photographs depicted in the report. Incidentally, the 1971 survey does NOT list milestone 52. I doubt that milestone 52 was created after 1971, so perhaps it was lost or hidden or, because it was not on the route of the Upper Boston Post Road, was accidentally overlooked. Milestone 53 does give me pause, as it seems to be in very good shape, especially as it is made of sandstone; other stones along the road, as we shall see, are significantly eroded. The remarkably unblemished surface of the stone makes me a little suspicious about its authenticity.

Another difficulty is that milestone 53, like it predecessor milestone 52, is not in phase with the actual distance from the putative ultimate destination, the Old State House in Boston. According to my calculations, milestone 52 should be located in front of the property once belonging to the Upham family, just before Chapel Mills. Milestone 53, although located exactly one mile from the current location of milestone 52, is only a quarter mile from the expected location of milestone 52 at 420 Main Street. In order to correspond to the actual distance from the Old Statehouse along the earliest route of the Upper Boston Post Road (or at least the earliest route I can document, which is the first quarter of the eighteenth century), milestone 53 would be located a little past Mannville Street, in the vicinity of 850 Main Street, directly across the street from Barber’s Crossing Road House. There is also some uncertainty about the original route of the road through Collier’s Corner and it is possible that the road did not pass this spot in its oldest incarnation as we shall shortly see, which would mean that the stone had to have been moved from its location on the earlier path through the area.

The current location of milestone 53 is, however, exactly 6 miles from milestone 47, which is located in the fence in front of The Oaks, the former Paine estate at 140 Lincoln Street in Worcester, now headquarters of the Worcester Chapter of the Daughters of the American Revolution. I discussed this milestone in my first entry on the city of Worcester, and will repeat my hypothesis again here: that milestone 47 was moved at some point from the center of Worcester and placed in front of this building in order to preserve it from destruction, as the area in which it originally would have been located, near the courthouse on Main Street in Worcester, was in a state of almost continuous redevelopment, and the stone may have been in danger of being lost or destroyed during one of the numerous construction projects in the last century in downtown Worcester.

It appears that, at some point, the subsequent stones may have been rearranged so that they were logically consistent with the distance to milestone 47, perhaps during the Colonial Revival period peaking in the 1920s, when many old buildings and other cultural artifacts were notoriously altered or “restored” to their “old-timey” look, a topic I have discussed many times in these essays. A more unlikely alternative scenario is that milestone 47, or one of the stones (44, 45, or 46) now missing between milestone 43 and milestone 47, might have been placed in an incorrect location when it was first measured out, and all subsequent stones followed the logic of said misplaced milestone. Milestone 43, currently located in Shrewsbury center, was itself moved in recent years from its original location near what is now an exit ramp for Interstate 290, but the original location of milestone 43 was almost exactly 43 miles from the Old State House in Boston along the route of the Upper Boston Post Road. Therefore any shift of the stones must have occurred after milestone 43.

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Turning the Corner

This vestigial section of Willow Hill Road ends abruptly at Kettle Brook in Collier’s Corner. Local histories suggest that travelers once crossed Kettle Brook at this spot and that this road was once the route of the Upper Boston Post Road through Collier’s Corner, passing along the ridge west of Main Street uphill before emerging at the site of St. Joseph’s Church. The putative road up the hill has long since disappeared.

Although the current route of the Upper Boston Post Road is along Main Street from Collier’s Corner, the original route up this hill is uncertain. Emory Washburn provides some details about the development of the road in Cherry Valley, quoting from the original 1723 town records of the plan to widen the “Country Road from Worcester to Spencer,” as Washburn calls it: “from Richard Southgate’s house, along in that way which was formerly in use when the town was laid out, and hath now trees marked on the north and north-east sides thereof all along, and which, in like manner, is to be four rods wide, and Mr. Southgate’s fence is to be altered, and the road, as now designated, to be cleared for the convenience of better passing with horse and teams; and so to Nathaniel Richardson’s house; and from that to the said Meeting-house, by the old road up the hill, as now in use, without taking any notice of the trees within John Smith’s fence, though formerly marked.”⁴² Washburn goes on to describe the locations of the houses referenced in the town records; “Richard Southgate’s northwest from where John Southgate lived, — the house now gone; Nathaniel Richardson’s, the house opposite to the present Catholic Church. John Smith’s land was on the east side of Meeting-house Hill.”⁴³ In an earlier section of his book, Washburn tells us that “John Southgate lived in the easterly part of town, near the junction of the county road from Charlton with the old Great Road, where it passed along the side hill, instead of its present course through the valley.”⁴⁴

In yet another section of his more than 400-page (467 pages) book Historical Sketches of the Town of Leicester during the first Century from its Settlement Washburn examines the early “highways” of the town of which the “Country Road” or “Great Road” is the most important, having been the “principal road in the town, from the first.”⁴⁵ He goes on to say that “the direction of this road through the town has been changed, from time to time, within the recollection of the present generation,” noting that it passed over the summit of Chestnut Hill, “and, from what is now Mr. Dickinson’s factory, it passed up just above the house formerly of Matthew Watson, and along the brow of the hill to where Waite Tavern used to stand.”⁴⁶ Waite Tavern was once located opposite the site of St Joseph’s Catholic Church, at the top the hill next to Waite Street as we shall see. Washburn published his book in 1860, at which time Dickinson operated the factory on the north side of Kettle Brook (discussed above). The house of Matthew Watson, built in 1720, “stood about 60 rods northeast of Deacon Lyon’s, on land now of Joseph Denny, Esq.”⁴⁷ I can’t sort out whether there was more than one Matthew Watson, because Washburn also states that Matthew Watson “lived in Cherry Valley, where Nathan Holman lives.”⁴⁸ Nathan Holman’s house on Woodford’s map of 1855 is in the middle of Cherry Valley east of Dickinson’s mill off of Church Street, south of Kettle Brook, so this seems a very unlikely route of the road; therefore it seems likely there is another Matthew Watson whose house from 1720 is described above, clearly located between Dickinson’s factory on Kettle Brook near Collier’s Corner and Waite Street at the top of the hill.

Other clues to the old road come from more recent sources. Don Lennerton, a local historian in Leicester (and father of Joe Lennerton, who gave the the aforementioned presentation on the Cherry Valley Flood), informed me in a conversation that the original route of the Upper Boston Post Road diverged from the current road around Collier’s Corner, and followed a now-lost path slightly west of the current road near Monterey Drive up to St. Joseph’s Catholic Church opposite Waite Street. A similar argument is made in Where the Wild Strawberries Grow: A Pictorial History of Leicester, which argues that the original road ran “from Chapel Street over the lower section of Willow Hill Road west of the greenhouse and behind the houses which are now on Monterey Drive. The road came out at St Joseph’s Church.”⁴⁹

It seems plausible that the original road followed Willow Hill Road at Collier’s Corner for a short distance before turning to climb the hill. Washburn, describing the route to Charlton before the construction of the Stafford Turnpike in 1806, discusses the origins of what is now Willow Hill Road, as “the road leading by the Henshaw Place into the Great Road, at what is now Dickinson’s woolen mill.”⁵⁰ In a footnote, he describes the road being laid out by the town in 1739 “through the land of Southgate’s”, which refutes any notion that the original route of the Upper Boston Post Road might perhaps have followed Willow Hill Road much beyond the site of Dickinson’s Woolen Mill, which is clearly shown near Kettle Brook along the curved section of Willow Hill Road that is now a short dead-end road into Kettle Brook at Collier’s Corner.

The house built in 1765 by John Southgate was “located on the hill above the junction of Willow Hill Road and the Post Road”⁵¹ The house was later owned by Joshua Henshaw, and was purchased by Hugh Rice in 1868. It was torn down in 1899.⁵² Woodford shows a Henshaw house northwest of the junction of Cross Street and Willow Hill Road. The 1870 map has an incorrectly drawn intersection at Collier’s Corner, but the 1898 map shows the estate of “Mrs. Hugh Rice” a few yards west of the same junction of Cross Street and Willow Hill Road.

A hypothetical route of the old Upper Boston Post Road might have passed through the area as follows: Instead of going straight across Kettle Brook the old road would have taken a left curve on Main Street after it passes Chapel Street, much as the new road does today (see photo). Then the old road would have continued across today’s Route 9 to cross Kettle Brook and reach the vestigial dead-end section of Willow Hill Road (see photo). The road would then continue along Willow Hill Road up the hill to the intersection with Cross Street. The old road would then have continued through the woods on the other side of the street up the “side hill” instead of through the “valley” as Washburn called the current route of Main Street, to reach the top of the hill at the junction of Main Street and Waite Street. This route would have passed east of the houses on Monterey Drive but west of Main Street, on the “side” or slope of the hill as shown on the topographical map below. This putative road seems somewhat impractical, and it is perhaps unsurprising that the route was altered at an early date.

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Topographical map of the area from Collier’s Corner to Waite Street near the site of St.Joseph’s Catholic Church (recently demolished as described below). The original route of the road may have been somewhat different from the current route along Main Street up the hill. One hypothesis, shown by the black line, is that the road followed Willow Hill Road from Chapel Mills across Kettle Brook and then headed uphill west of Main Street but east of Monterey Drive before coming out near St. Joseph’s Church. This seems quite a steep climb. If it was the route of the original road it was understandably altered, likely well before 1795, and certainly by 1831 (see above map).

*****

The map of Leicester drawn by Peter Silvester, Jr. in 1795, although not as clearly detailed as later maps, is at least to scale, and the route of the road from Kettle Brook to the meeting house seems roughly similar to the current route, especially if the old map is laid out on a current map. The route of the road as shown on the more detailed map 1831 map of Leicester is clearly discernible and appears nearly identical to the current route, as does the route on Woodford’s 1855 map. If there was an old route up the hill, it was likely no longer in use by 1795 and certainly was not in use by 1831.

It is therefore very likely that the present shape of Collier’s Corner was the result of a newer road built directly across Kettle Brook, the road that crosses Kettle Brook just west of Chapel Mills. This road is likely to have existed by 1795 as the map of Peter Silvester shows the road crossing Kettle Brook a substantial distance north of the bend in the brook, while Willow Hill Road crosses Kettle Brook almost exactly on the bend in the brook. The 1831 map of Leicester also shows the crossing at roughly the same location, consistent with the crossing as described in my walk above, and also shows a sharp bend in Willow Hill Road consistent with the current shape of the contemporary road leading away from the “Great Road,” today’s Main Street.

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A Different Milestone!

Another milestone. This property on the road leaving Cherry Valley in Leicester was the first along the route of the Upper Boston Post Road I observed with signs or flags of support for Donald Trump. This is also the first town along the road in which a majority of voters supported Donald Trump in the recent election.

Regardless of the route the road might once have taken uphill or of the original location of milestone 53, this section of Main Street is today part of the 53rd mile along the route of the Upper Boston Post Road. Across the street from the wall in which milestone 53 is embedded, the house at 523 Main Street represents a milestone of a different sort, and also a clear indication that the gravitational pull of the Boston metropolitan area is weakening. When I walked past the somewhat disheveled house nearly opposite milestone 53 for the first time in September, 2024, the house was festooned with a plethora of flags supporting Donald Trump. Remarkably, this is the first time I have observed a Trump sign along the entire road to this point. Obviously, this is not to say there are no Trump supporters living within 50 miles of Boston. However, Leicester, Massachusetts also happens to be the first town along the route of the Upper Boston Post Road in which a majority of votes were cast for Donald Trump in the 2024 Presidential Election. The road passes through 12 towns and cities from Boston before reaching Leicester and in not one of these towns did the Republican candidate for President of the United States and eventual winner, Donald Trump, receive even 40% of the vote, while Kamala Harris, the Democratic nominee for President, received 59% or more of the vote in every single town or city along the way, including 62% of the vote in Worcester, the city through which I most recently walked.

The data for the 2024 Presidential Election for each town thus far along the route of the Upper Boston Post Road is shown here, the number representing the percentage of the votes received by the Democratic nominee for President, Kamala Harris: Boston-77%; Brookline-84%; Newton-78%; Watertown-75%; Waltham-68%; Weston-69%; Wayland-77%; Sudbury-74%; Marlborough-61%; Northborough-64%; Shrewsbury-59%; Worcester-62%. The data is still consistent even if you include the alternate routes I have followed and written about in these essays, via Charlestown ferry, for example: Somerville-84%; Cambridge-87%; or the alternate road through Framingham: Framingham-69%; Southborough-67%; Westborough-68%.

From Leicester onward the data looks strikingly different. The data for remaining towns along the route of the Upper Boston Post Road in Worcester County is as follows: Leicester-45%; Spencer-44%; East Brookfield-41%; North Brookfield-41%; Brookfield-45%; West Brookfield-48%; Warren-40%. The towns along the road in Hampden County: Brimfield-43%; Palmer-43%; Monson-44%; Wilbraham-51%; Springfield-65%.

Worcester County as a whole also voted for the Democratic candidate, albeit by a relatively narrow (for Massachusetts) ten-point margin of 53.6% for Harris and 43.7% for Trump, as did Hampden County, the next county along the road (also a ten-point margin, 53.2% D to 43.4% R). This house with its Trump flags proudly flying over the Post Road does, however, represent a political shift on my walk across Massachusetts along the route of the Upper Boston Post Road, as all the towns beginning here in Leicester and continuing west to Wilbraham, the town immediately east of Springfield along the road, voted for Donald Trump in the 2024 Presidential Election. Granted, this is not exactly the same as walking through places like Wyoming or Tennessee, where Trump got more than 70% of the vote in virtually every county (large cities like Memphis and Nashville being very notable exceptions) and almost 90% of the vote in quite a few counties. Kamala Harris won every county in Massachusetts; the lowest percentage of the vote received by Kamala Harris in any town along the route of the Upper Boston Post Road was 40% of the vote in Warren, the last town in Worcester County along the road. Yet there is a noticeable difference between the towns I have hitherto walked, which collectively gave more than 2/3 of their vote to the Democratic candidate, and the towns along the next 40 miles of the road, where Trump received more than 50% of the vote in each one of the next ten towns. Why this happened and what it represents is a topic which I shall explore as I walk through each of these towns in Worcester and Hampden counties.

The area covered in this essay, including this section describing the walk from Collier’s Corner to Mannville Street, is all part of Precinct Two, one of the four electoral precincts in Leicester. An examination of the data in Leicester at the precinct level supports the idea that Cherry Valley, the “east-facing” Blackstone River watershed part of Leicester which comprises most of Precinct Two, is a transition zone between the Worcester and Boston-oriented part of the road, and the more rural area represented by the towns in the French River and Quaboag watershed areas, of which the other three precincts in Leicester are a part. The town of Leicester voted for Donald Trump over Kamala Harris by 3,310 votes to 2,822, or 52.14% to 44.45% of the total votes cast in the town (216 votes, or 3.41%, went to other candidates or were left blank). Trump won Precinct Two by a total of only two votes, 756 to 754, at 48.65% to 48.53% (with 44 votes, or 2.83%, for other candidates or blanks totaling 1,554 votes) a virtual dead heat. The other three precincts all went for Trump by at least 52%, with Harris receiving less than 45% of the vote in each of the three remaining precincts.

Precinct Two in Leicester is an excellent example of where things went wrong for the Democratic candidate in the 2024 Presidential election. Although Donald Trump won Precinct Two in the 2016 election against Hillary Clinton (by 669 votes to 640 votes), Joe Biden actually won Precinct Two in the 2020 election. In 2020 Biden received 794 votes to Trump’s 752 votes. In 2024 Trump received 756 votes; in other words, Trump managed to gain only four votes from 2020 to 2024, but Harris got 40 fewer votes than Biden got in the previous election. The pattern here was duplicated in virtually every swing state contested in the most recent election; it was not so much a question of Trump making dramatic inroads as is often portrayed in the media, but rather a loss of enthusiasm on the part of some segment of Democratic voters, which propelled Trump to a return to the White House. The total number of votes cast in Leicester in the 2024 election was 6,348 (including blank ballots), while voters cast 105 more votes in the 2020 election in Leicester, for a total of 6,453. Trump improved by more than 5% on his 2020 performance with 164 more votes, while Harris lost 279 votes compared to Biden (2,822 votes to 3,101 votes for Biden), a drop of nearly 9%. Although Trump clearly gained more votes, it also true that the net result of the 2024 election was that roughly 2% of the electorate, more than 100 voters in Leicester, just decided not to vote and that number disproportionately impacted the Democratic candidate. This transition zone, Cherry Valley in Leicester, where Harris lost 40 votes and Trump gained only 4 votes, is exactly the type of place Democratic Party operatives need to examine carefully to sort out where things went wrong and what needs to be done if the party plans to remain viable in future elections.

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Reaching New Heights

Although the ties with Boston may be fraying as I move west along the road as it begins a steep uphill climb, a sign along the south side of Main Street is evidence that Leicester is still within the gravitational pull of Boston and its seemingly endless development boom. The sign, which fronts a wooded area, is for “Skyview Estates,” and includes a plan featuring 68 units to be developed on 34 lots, while exclaiming that the property is “Shovel Ready!!!” (exclamation points included!!!). Main Street climbs from an elevation of 752 feet above sea level at the Kettle Brook crossing to a new record height of 873 feet above sea level a half mile along the Upper Boston Post Road at the intersection with Waite Street. Woodford’s map of 1855 shows only two properties along the entire stretch of road between Collier’s Corner and Waite Street, and only a handful of houses appear even as late as 1898 on Plate 49 of the Worcester County Atlas. This section of the road, still lined mostly with woods save for a few recently-built houses, is at the forefront of development in Leicester after centuries of somnolent repose.

It is a bit disappointing, after devoting so much effort in this essay to exploring the mystery over the precise route up the hill from Collier’s Corner to Waite Street, to report that the current route up the hill is uninteresting. Along with the aforementioned woods and the likely future development, there is a newer unimpressive development on the east side of the road. Otherwise there are a few houses scattered along the road or along newly-developed cul-de-sacs leading into the woods off Main Street before I reach the top of the hill at the junction with Waite Street. On my most recent walk through the area (October 2025), even reaching the new height along the road turns out to be disappointing.

Directly opposite Waite Street, on my first walk through the area (September 2024), was the impressive hilltop St Joseph Catholic Church (see photo), a building which has subsequently been demolished. I had a premonition that the building was not long for this world as it was marked with a large red X which, as we have seen before, means that firefighters should not attempt to enter the building as it has essentially been condemned. To me it is a bit surprising that a Catholic Church, particularly one as old as St. Joseph’s Church, should be demolished. Although St Joseph’s is the original Catholic Church in Worcester, two parishes in Leicester were merged in 2014 and the congregation moved en masse to celebrate mass at the other parish church, St. Pius X, a modern church closer to the center of town. A letter published on July 2, 2025 on the combined parish website by Father Robert Loftus, pastor of St. Joseph-St. Pius X Parish since 2011, confirmed that St. Joseph had been demolished: “I write to you today as we have witnessed the demolition of a very precious piece of the faith life (and community life) of Cherry Valley and Leicester. The Church of Saint Joseph has been proudly and beautifully representing our Catholic Faith’s presence in Leicester/Cherry Valley since January 2, 1869.” The site notes that Catholic mass has been officially celebrated in Leicester since 1855 with the establishment of St. Polycarp.⁵³ By 1867, the church had grown and the cornerstone of St. Joseph church was laid, and the first service took place in 1870. In 1901 the church was expanded to become the building shown in the photograph above, which has now been demolished.

A large memorial dedicated to First Lieutenant James Sugrue of the US Army Air Force, killed in action in North Africa, March 1945, sits opposite the church. It was in this location, at the corner of Waite Street, that the house of Nathaniel Richardson mentioned by Washburn above, was located. Richardson was one of the first settlers in Leicester and ran the first tavern in the center of town as we shall see in the next entry. He died in 1728. Joseph Denny’s map (created in 1860 and found in Washburn’s book) of the plots of land acquired by each of the original settlers of Leicester (1714-1717) shows Nathaniel Richardson with two plots: the first is the land now at the northwest corner of Paxton Street and Main Street, where his tavern was located and where the Knight House/Swan Tavern is currently located (as will be discussed in the next entry), and a second lot corresponding to the location of the house mentioned by Washburn at the top of the hill, where Waite Street and the property of St. Joseph’s Catholic Church are located.

Richardson’s daughter Deborah married Jonathan Sargent in 1726, who opened on this second lot what became the second tavern in town (after Richardson’s, mentioned above, in the first lot). According to Washburn “It was built and occupied as a tavern as early as 1727. Mr. Sargent occupied it till his death. He was succeeded by his son Phinehas, who occupied it till his death in 1776. Upon his death, the estate was purchased by Nathan Waite, who owned it till his death, but discontinued it as a tavern several years before that time.”⁵⁴ Waite died in 1818, aged 74, and Amos Hill Coolidge notes that the building “was afterward torn down.”⁵⁵ The tavern is not mentioned in the list of taverns along the “Road from Boston, Westward, thro’ Worcester to Springfield on Connecticutt River” in the Vade mecum of 1732, although Nathaniel Richardson’s tavern is listed. Nor is the tavern listed in any of the almanacs published after the Revolution, although the almanacs include later incarnations of Richardson’s tavern as well as other taverns along the road beyond Waite’s, which indicates that perhaps Waite had ceased operating the tavern before 1785, the earliest almanac I have examined which mentions taverns in Leicester.

The absence today of a tavern here on the hill or of any evidence of the original Richardson house is unsurprising as we have just learned that the tavern has been gone for well over a century. It is a little more surprising to have passed an imposing elegant church building with nineteenth-century roots along the road on my first walk through the area, only to return on a later walk to find the church demolished. My initial optimism that perhaps the less-populated towns west of Worcester might be more capable of preserving their heritage than big cities like Worcester or Boston is quickly being converted to resignation as I begin to realize that the loss of cultural artifacts along the road has been a constant for as long as the road has existed. The loss of St. Joseph’s Church is not an anomalous event, it is part of a long heritage of loss that has become a major theme running through the entire project. Part of the purpose of this project has clearly become to document what is there as I walk along the road now because, sooner or later, some of it will surely disappear. This is not what I intended when I began the walk but the best laid plans etc…

*****

Out of the East

*Leaving the Blackstone Valley and heading up Strawberry Hill. Main Street at Winslow Street.*

From the Waite Street junction the road heads downhill briefly for three hundred yards, passing another new development (six units) on the north side of Main Street, before reaching Mannville Street. A few yards beyond Mannville Street the road passes over a narrow creek, which disappears into a small marsh south of Main Street behind Barber’s Crossing Road House. This seemingly insignificant stream is actually the first sign that I have crossed out of the Blackstone River watershed and have entered the French River watershed, whose waters flow in a southward direction into the Quinebaug River, which joins the Shetucket River at Thompson, Connecticut, and continues south until it drains into the Thames River, which flows into Long Island Sound at New London, Connecticut. Most of Leicester is part of the French River watershed, and most of the rest of the Upper Boston Post Road through Leicester passes through the northern end of this watershed, before crossing over into the Quaboag River watershed as the road crosses into Spencer.

After a few more yards the road splits again, with the old road continuing straight along Main Street, while most of the traffic follows South Main Street/Route 9, a road built to bypass the historic center of town first appearing on maps of Leicester in the 1930s.⁵⁶ Main Street was the only east-west road through the center of town on the all maps of Leicester published before the 1918 Sanborn Insurance map so it is clearly the the original route of the Upper Boston Post Road. More evidence appears almost immediately as I begin the walk up Main Street and encounter a sign reading “Leicester Center National Register Historic District.” The center of Leicester has a wealth of interesting buildings and artifacts with historic links to the Upper Boston Post Road, so I will stop this part of the walk through Leicester here at the foot of what was once called Strawberry Hill at the junction of Main Street and Winslow Street. This feels appropriate as it is almost exactly fifty three miles from Boston at the expected location of the 53 milestone, which we passed back at Collier’s Corner. With a nod to this last link to Cherry Valley, to the Blackstone River, and to Worcester, it is time to shift gears and head up the hill to see the view west.

*****

Special thanks to Don Lennerton for pointing out the change in the route of the Upper Boston Post Road around Collier’s Corner.

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Dedicated to Geoff Nicholson, walking artist.

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Distance traveled in this entry along the route of the Upper Boston Post Road: 2.0 miles.

Note that the above distance does not include the various alternative roads walked and discussed in this entry.

Total Distance traveled thus far along the route of the Upper Boston Post Road from Worcester Courthouse to Springfield “Meeting House” (six entries): 6.3 miles.

Total Distance traveled along the original route of the road from the Old State House in Boston for this project: 53.0 miles.

Total Distance covered for all the walks described in Boston Rambles: 114.6 miles

Posted in Demographics, Elections, History, Milestones, Population, Roads, Upper Boston Post Road on 31 October 2025 and tagged Census data, Elections President, Leicester, Milestones, Old Roads, Population, PostRoad
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Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Leicester, Massachusetts, #1.

Savoring the Fruits of Leicester

Part One– A Walk Through Cherry Valley

Upper Boston Post Road #20 (UBPR #20).

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Leicester, Massachusetts, #1.

Savoring the Fruits of Leicester

Part One– A Walk Through Cherry Valley

Upper Boston Post Road #20 (UBPR #20).

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