Walking The Upper Boston Post Road From Worcester To Springfield: An Overview
Upper Boston Post Road Entry #19 (UBPR #19)
“To Boston from the Meeting House 96½ Measured Miles, Boston Road”
From “A Plan of the Town of Springfield, Massachusetts taken from an actual survey thereof made since the Resolve of the General Court passed June 26, 1794.” Israel Chapin, Surveyor, dated “the Twentieth Day of May, A.Dom. 1795.”
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“47 Miles from Boston, 50 to Springfield”
From the milestone in front of the Oaks, the former estate of the Paine family in Worcester, Massachusetts. Date uncertain, likely eighteenth century.
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The distance from the old Worcester County Courthouse on Main Street in Worcester to City Hall on Court Street in Springfield following the route of the Upper Boston Post Road is roughly fifty miles. In the colonial era Springfield was an important stop along the route of the Upper Boston Post Road, the point at which the road turned south and followed the Connecticut River to Hartford, after which the road continued to New Haven and on to New York City. However, as I discussed in the previous entry, the section of the Upper Boston Post Road west from Worcester to Springfield was bypassed with the opening of the Stafford Turnpike in 1810 which provided a shorter and more direct route from Worcester to Hartford. Although the Upper Boston Post Road continued to serve as the principal road to Springfield and to Albany (with a few more deviations along the way as we shall see in future entries), it was no longer the “main” road from Boston to New York.
Prior to embarking upon this project I had never set foot in any of the towns through which the road passes between Worcester and Springfield, although I had passed through some of the towns along the Massachusetts Turnpike (Interstate 90) en route to other places like the Berkshires, upstate New York, or Shelburne Falls in the Pioneer Valley, where my sister lived for many years. To me this area has always been a mysterious place, an area where many of the farms are located from which I buy much of my food at the local farmers market, but an area that is, in truth, the Massachusetts equivalent of “flyover country” for the bulk of the population who reside in the Boston area. This is not meant as a criticism of the area, it is merely an acknowledgment that in the daily lives of most of the residents of Boston (in the sense of Metro Boston) the towns between Worcester and the Connecticut River are not generally the first places that comes to mind.
The towns along the road through the area are lightly populated for the most part: while Worcester (206,518 residents in the 2020 Census) and Springfield (155,929 residents in the 2020 Census) are the second and third largest cities in Massachusetts, the eleven towns along the route of the Upper Boston Post Road between the two cities have a total combined population of 80,818 residents according to the 2020 United States Census. These eleven towns cover an area of 283 square miles, which is six times the area of Boston (48.3 mi2 of land area) and more than seven times the area of either Worcester (37.4 mi2) or Springfield (31.9 mi2). Not only are the towns lightly populated, they are not very densely populated, and the old road frequently passes through some very tranquil areas. The view from the Massachusetts Turnpike as it passes through most of these towns is essentially of forests with an occasional lake or pond to break up the monotony. While this impression is misleading, it is fair to say that these towns are relatively unpopulated compared to the towns along the route of the Upper Boston Post Road I have followed thus far. Every single town which I have already passed through on this project has a larger population than any of the eleven towns I am about to visit on my way to Springfield.
Collectively, these eleven towns do not generally have any “big ticket” tourist attractions to draw visitors, nor are there any colleges or universities along the road. The main road today west from Boston to Springfield is the Massachusetts Turnpike which has only a couple of exits between Worcester and Springfield, so the modern road almost literally passes by most of these towns. It is just plain easier to drive to “more exciting” places like the Berkshires, New Hampshire, or Cape Cod than to make the effort to visit these towns as a rule. Again, this only adds to the mystery of my forthcoming adventure.
The towns west of Worcester are also located in an area that is exceptionally hilly compared to the area through which the road has passed in the first fifty miles from Boston to the border between Worcester and Leicester. At 787 feet above sea level, the end point of the previous entry at the Leicester/Worcester border was the highest point along the entire route of the Upper Boston Post Road for the first 51 miles from the Old State House. The road goes through even higher terrain west of this point, as can be seen from the topographic map of the area below. Once over the hills of Leicester and Spencer, the route of the Upper Boston Post Road generally follows the course of the Quaboag River and the Chicopee River before dropping into the Connecticut River Valley in Springfield. However, the road was notoriously difficult to travel along in this area, as we shall see, which only adds to the mystery.
These towns also happen to be at the center of what passes for a “red” or Republican stronghold, a place where Donald Trump has done quite well over the years relative to his generally abysmal performance overall in Massachusetts. This only adds to the element of mystery that beckons as I begin my walk west from Worcester, the second largest city in Massachusetts, to Springfield, the third largest city in the Commonwealth. Every town between Worcester and Springfield along the road, with the sole exception of Wilbraham, the town immediately east of Springfield, voted for Donald Trump in the most recent election. As I have long been interested in the analysis of data, particularly about demographics and electoral politics, this was not a surprise to me, but this walk allows me to go beyond the numbers and to meet people along the way in an effort to try to understand exactly what it is about Trump’s message that seems to resonate with a majority of the voters in these small towns.
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I conceive of the walk from Worcester to Springfield along the route of the Upper Boston Post Road as a distinct section of the road, and so this entry will be an overview of the whole walk before I return in future entries to the more typical format of discussing the road one town at a time. This particular section of the project will have three main objectives. First, and most importantly, I want to document the route of the Upper Boston Post Road through the area, including the many changes that have been made over the years. It turns out that there are numerous milestones along this section of the road and many other artifacts testifying to the importance of the road, particularly in the colonial era, much of which has been carefully documented by local historians, and I hope to share this information with the reader. A careful description and reconstruction of the oldest version of the road is, as always, the principal goal of this project.
Secondly, this project was inspired from the beginning by the idea that I did not have to travel far to make a pilgrimage. I originally conceived of the project as a domestic alternative to walking the Camino de Santiago in Spain, a way to get out and put one foot in front of the other and discover what was along the old road to New York that passed by my house, the Lower Boston Post Road. Perhaps this more recent walking project along the route of the Upper Boston Post Road has been a little less spontaneous than the previous project and a little more focused on the detailed analysis of the road itself, but there is still an element of surprise and mystery every time I head out to walk a new section of the road. So it is particularly appropriate that I have reached an area about which I know relatively little as I begin to write these entries describing my walk along the road through these towns. This section of the walk, more so than places like Worcester, Sudbury, or indeed Boston and Cambridge, will be a voyage of discovery unlike any of the sections of the road about which I have already written. The second objective then is to describe the road as I find it today: what remains and what is lost, what is interesting and what is not, what the road looks like from the point of view of somebody walking along it for the first time.
Finally, as I write, it is clear that Donald Trump will once again become President of the United States. I wrote extensively about his path to victory in the aftermath of the 2016 election (see these entries for example), partly as catharsis and partly in order to try to understand how he won and what the data suggested about the political future of the country. I believe my analysis was correct in the short term but completely inaccurate in the long term, as is clear from not only his victory in the Electoral College, but also his victory over Kamala Harris in the national popular vote. In my first series of essays on the first Trump victory I focused on Pennsylvania, as it was and remains the most important state in determining the overall outcome of the election. Neither Clinton nor Harris had any real path to victory other than through Pennsylvania and so I was interested in trying to understand the electoral and demographic dynamic of the state in order to try to predict what the future might bring. Needless to say, we now know the future: For better or for worse Donald Trump will be running the show for the next four years.
The first town west of Worcester along the route of the Upper Boston Post Road is Leicester, Massachusetts. Leicester is also the first town along the road from the Old State House in Boston, a distance of 51 miles from the start of the road, which gave a majority of its votes to Donald Trump. The towns west along the road, including Spencer, East Brookfield, North Brookfield, Brookfield, West Brookfield, Warren, Palmer, and Monson all voted for Trump as well.1Wilbraham, the eastern neighbor of Springfield, remained in the Democratic column, along with the cities of Worcester and Springfield. I now have the opportunity to do what I never did in the aftermath of Trump’s first victory, to walk through a section of the country which can properly be called Trump Country and to describe what I see along the way.
One final note to those who might be worried that these entries will become political rants about a person angry at the result of the election. As I said earlier, for better or for worse Donald Trump is about to return as President of the United States. Personally I think it is for the worse, and my faith in the United States of America as the welcoming and open country I have always believed it to be, the proverbial land of opportunity, is about to be sorely tested. I know the country has not always lived up to its billing and that there are many who believe that the aspirational America of dreams is just a charade or the naive wishful thinking of elites living in their blue bubbles. To that I say bullshit. I do say, however, that I always try to keep my personal opinions about the state of events from influencing how I write about the road. The road is a document that needs to be read carefully and with an open mind in order not to fall into the trap of romanticizing it or painting an overly flattering (or unflattering) portrait. I hope that the long and detailed descriptions in these entries of sections of the road that I have not particularly enjoyed were at least honest. I also hope that any analysis I provide in these essays is honest and transparent. David Brooks, a conservative opinion writer for the New York Times, published an article recently with the headline “Voters to Elites: Do You See Me Now?”, to which I respond (although how I became elite is a mystery to me, but I digress): I am literally walking out to meet you in your own town!2I will limit to the footnotes my editorial opinions of this style of article and the other fatuous commentators who seem to think that anybody who went to college is some sort of effete caviar-slurping twit: first of all, fuck you David Brooks and all your dickhead colleagues. You don’t have the first clue what you are talking about! Secondly, the paintbrush that the so-called elite supposedly uses to paint a picture of the (I guess) not-elite, is being wielded to paint in equally broad brush strokes a distorted picture of the 48-49% of people who did not support Donald Trump. Try some proper analysis not mockery.
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The Upper Boston Post Road was the main road west from Boston to New York in the colonial era. This road passed through Worcester and then continued on to Springfield. After Springfield, the traveler typically crossed the Connecticut River and then continued south from West Springfield into Connecticut. The Upper Boston Post Road in Connecticut continued south to Hartford and then on to New Haven on the coast of Long Island Sound. Here it merged with the Lower Boston Post Road, another important old road which passed south from Boston through Massachusetts into Rhode Island and then continued along the coast of Connecticut to New Haven. The road continued west as the Boston Post Road into New York, ending in Lower Manhattan.3For more on this topic, including my walk along the Lower Boston Post Road, see my website Walking the Post Road
In 1795 the distance to Boston from the Meeting House in Springfield was 96½ miles, according to the official map of the town produced by surveyor Israel Chapin. Every town in Massachusetts was required to produce a detailed map at a scale of “200 rods to one inch” by a Resolve of the General Court on June 1794. Most of the maps were surveyed sometime in 1794 and most of the final copies were completed in May 1795 and submitted to the state. An official map of the Commonwealth of Massachusetts was produced from these detailed maps by Osgood Carleton in 1795 (see above for an image of the section of the official map relevant to this entry and below for a section of Chapin’s map of Springfield).
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Each map was required to contain certain features, such as accurate descriptions of the borders of the town with neighboring towns, any rivers and other major bodies of water that were found in the town, and a depiction of the route of major roads through the town, including any bridges over the rivers or streams which crossed the road. Another required feature was a calculation of the distance from the center of the town, usually the location of the meeting house, to the “metropolis of the Commonwealth,” which was the State House in Boston, then at the corner of what is today Washington Street and State Street. A final required calculation was the distance from the meeting house/center of town to the courthouse in the county seat. For example, the map of the town of Marlborough, a town along the route of the Upper Boston Post Road located in Middlesex County, has an inscription that runs across the middle of the map that reads “Reputed Distance from the centre of Marlborough to the Court house in Cambridge is 26 miles. Reputed Distance from the centre of Marlborough to the State house in Boston is 30 miles.”4There was another circuit court held in Concord which was also included, the distance being 14 miles. Also note that in the early 1790s a new bridge was opened across the Charles between Boston and Cambridge that shortened the distance to the State house by a couple of miles in some cases. Sometimes the distance was calculated using the new route but mostly it was calculated using the old route. In the case of Sudbury, both routes are helpfully listed. According to the route I have so far followed that I believe matches the route of the Upper Boston Post Road that a typical traveler would have taken from Marlborough to Boston in the eighteenth century before the advent of new bridges and turnpikes that created new and shorter routes, the distance from the meeting house in Marlborough to the State House in Boston is about 30.5 miles.
In the case of Worcester, which was the county seat, or shire town, of its namesake county, the distance to the State House in Boston was measured from the Worcester County Courthouse which, for most of its long history, was located along Main Street in Lincoln Square. The old courthouse building today is an apartment building called Courthouse Lofts as a new Worcester County Court building was opened a little further along Main Street in Worcester in 2007. The map of Worcester produced by John Pierce and David Andrews, dated May 28, 1795, states “the distance from Boston to Worcester Court-house is 47 miles.” There is no need for a second distance as the courthouse is the center of the county. As the shire town of the county of Worcester, distances from each town in the county to the Worcester County Courthouse were reported on town maps. The map of Leicester, the next town west of Worcester along the route of the Upper Boston Post Road, is a typical example. On the map of the town prepared in 1795 by Peter Sylvester the distances are listed as follows: “Congregational Meeting House is 54 miles from Boston and 7 miles from Worcester Court House.”5For more on the Worcester County Court House, see my entry Worcester, Part Two.
There is an old milestone (see photo above) that has been embedded in the fence of the old house at 140 Lincoln Street in Worcester, a little more than half a mile from the old Court House on Main Street. Construction of the mansion called “The Oaks” was begun in 1774 by Judge Timothy Paine, a Tory sympathizer who very nearly was forced to flee Worcester in the 1770s, but managed to remain in his house until his death in 1793. Today the building is the headquarters of the Worcester chapter of the Daughters of the American Revolution.6For more on the Paine family and the Oaks, see my entry Worcester, Part One. The house itself is only about 46.1 miles from Boston according to my calculations, while the old Court House, according to my calculations, is 46.7 miles from Boston .
The milestone in front of the house reads “47 miles from Boston 50 miles to Springfield.” It is my hypothesis that the original home of the old milestone was once on Main Street, perhaps near the Palladium, close to the building housing the Dead Horse Hill Restaurant, which is on the site of the Heywood Tavern, first opened in Worcester in 1722.7For more on Heywood’s and other taverns in the center of Worcester, see Worcester, Part Two. This is a couple of hundred yards south of the old Court House, which is listed as 47 miles from Boston on Pierce and Andrews’s map of Worcester. The stone was likely moved to its current location in order to preserve it in a more tranquil location as downtown Worcester continued to develop in the early twentieth century. Silvester’s map of Leicester has the distance from Boston as 54 miles but the distance to Worcester Court House as 7 miles, thus 47 miles from Boston to Worcester, which is consistent with a location of the milestone closer to the courthouse than its current location. The contemporary distance from the First Congregational Church in Leicester to the old Worcester Court House building is 6.7 miles, also consistent with the 1795 maps and with the milestone.
On the milestone Springfield is listed as 50 miles from Worcester and Boston is 47 miles from Worcester, making the distance from Boston to Springfield a total of 97 miles. As we have seen, Chapin listed the distance from Springfield to Boston as 96½ miles, which is very close indeed to the number calculated from the milestone. Curiously, Chapin’s map is the only one I have encountered where the distance to Boston was calculated out to a fractional distance; all the rest round up or down according to need. Numerous milestones dot the landscape along the road west from Worcester, some of which have clearly been moved as we shall see in future entries, but their presence provides clues as to the course of the road through each town. Combined with an analysis of the old maps, the remaining stones will be particularly useful in helping to reconstruct the road as accurately as possible, hopefully as it was at the very end of the eighteenth century and, with luck, perhaps even earlier.
Along with the old maps and the milestones, there are also numerous reports and almanacs from the period, starting with the Vade mecum in the 1720s through to the early nineteenth century, which describe the location of taverns along the road through these towns at which travelers would have stopped. That the almanacs and reports of distances along the road need to be analyzed critically can be gleaned from a brief survey of the reported distance from Boston to Springfield in these sources, which range from a distance of 94 miles in the 1728 Vade mecum to 106 miles in a report from Major General Benjamin Lincoln to George Washington in October 1778. Fortunately, most of the distances reported converge in the range of 96-98 miles, consistent with the stated distances on the milestone in front of The Oaks in Worcester. Incidentally, Google maps tells me that a journey by car, mostly along Interstate 90 (the Massachusetts Turnpike), from the Old State House in Boston to City Hall in Springfield, is a distance 90.6 miles and should take about 90 minutes. A walk between the two locations, according to Google maps, is 90.3 miles in length, mostly following US Route 20, and can be accomplished in 33 hours of continuous walking. It will take me slightly longer to cover the distance.
Various travelers along the old road kept journals or diaries describing their experiences along the road, visiting some of the taverns listed in the almanacs and providing richly detailed reports on the state of the road and the quality of their accommodations, often including vivid descriptions of the tavern keeper and the other customers. Samuel Sewall, John Adams, George Washington, Jacques Pierre Brissot de Warville, Dudley Woodbridge, Timothy Dwight, and others provide useful and frequently entertaining information about the state of the Upper Boston Post Road from the late seventeenth to the early nineteenth century. I will continue to enjoy their company on the next fifty miles of this walk just as I have done in the first fifty miles of this walk.
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This entry marks the completion of the walk from Boston to Worcester, the first phase of the route from Boston to New York along the route of the Upper Boston Post Road. The road to Springfield along the route of the road traversed by travelers in the eighteenth century, the road before turnpikes and new bridges changed the course of travel, is a distance of about fifty miles from the center of Worcester. Thus begins a new chapter in this project, a walk along the road from Worcester to Springfield.
As is often the case with my entries there is a caveat. This project technically begins at the center of downtown Worcester in front of the old Worcester Courthouse. However, I have actually already walked all of the road in Worcester, including the road to the border with Leicester, and presented it in five entries on Worcester. The first entry on the road in Worcester brought me to the old Court House in Lincoln Square, thus ending the first part of my project, the walk from the State House in Boston to the Court House in Worcester. The second entry on Worcester started in Lincoln Square and ended at City Hall, while a third entry dealt with the area around City Hall, and the last two entries (here and here) followed the road southwest out of Worcester along Main Street and Apricot Street into Leicester, the road Pierce and Andrews called on their 1795 map “the Road from Boston to New York.” My goal in these entries was to complete the entire walk along the route of the Upper Boston Post Road in Worcester before turning my attention to the road to Springfield. Thus I have already published essays about the first 4.3 miles of the road from Worcester to Springfield.
The border between Leicester and Worcester will thus be the start of the opening entry in the next chapter of this project. According to my calculations the distance along the road from the border between Leicester and Worcester to the likely original location of the 47 milestone between the old courthouse and the site of Heywood’s Tavern, now the location of Dead Horse Hill restaurant, is about 4 miles. If a “51 miles to Boston” milestone existed, it would likely be located along Sargent Street/Apricot Street (the name changes from Apricot Street in Worcester to Sargent Street in Leicester as it crosses the border) near the border between the two towns. Unfortunately, there is no 51 milestone today as far as I have been able to ascertain, but you will be able to read about the other milestones remaining in the town of Leicester in the next entry of this project when I write about the course of the Upper Boston Post Road in Leicester.
The Upper Boston Post Road continues in Worcester County west through Leicester and into Spencer. From Spencer the road passes through the “Brookfield” towns, all formed from the town of Brookfield (originally called Quabog): East Brookfield, North Brookfield, Brookfield, and West Brookfield. The road then crosses the Quaboag River and passes into the town of Warren, the final town in Worcester County. The Upper Boston Post Road continues across the town of Warren and then cuts across the northwest corner of Brimfield, the first town in Hampden County. From Brimfield, the Upper Boston Post Road crosses the Quaboag River a second time and passes through the town of Palmer. The road crosses the Quaboag River a third and final time on the western side of Palmer and the road then skirts the border between the towns of Palmer and Monson for over 2 miles (the Post Road is actually shown as the border between the two towns on the 1795 maps of the two towns as we shall see). The Upper Boston Post Road then crosses through the northern part of the town of Wilbraham and enters Springfield, where it continues for seven miles to Springfield City Hall near the Connecticut River. From here travelers to Hartford, New York, and beyond crossed the Connecticut River and followed the road that ran south along the west side of the river, but that chapter is fifty miles and many entries away in the future.
Next stop Leicester, Massachusetts.
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The following is a list of the towns along the road and a description of the official map of 1795 for each town. All maps 200 rods to the inch. (scale 1:39600)
Worcester County
Worcester (May 28, 1795. John Pierce and David Andrews. “The distance from Boston to Worcester court-house is 47 miles”). Miles 48, 49, 50, 51 all in Worcester (ie 47-48, 48-49, 49-50, and 50-51. Milestone 51 if it existed, would be near the border with Leicester. See entries #15, #16, #17, and #18 for Worcester from the old Court House to Leicester border. For the road to Boston from Worcester County Courthouse see entry #14. Distance in Worcester from the Courthouse to Leicester border= 4.3 miles.
Leicester (May 23, 1795. Peter Silvester. “Congregational meeting house 54 miles from Boston, 7 miles from Worcester court house”). See entry #20. miles 52, 53, 54, 55, 56, tiny bit of 57. Distance of the Upper Boston Post Road (UBPR) in Leicester=5.3 miles
Spencer (October, 1795. Unknown Surveyor. “Distan(ce) 59 miles from Boston and 12 miles distant from the Court House in Worcester”). See entry #21. miles 57, 58, 59, 60, tiny bit of 61. Distance of UBPR in Spencer= 4.4 miles
Brookfield (November 1794 [the survey taken, no date for final publication] Thomas Hale, Jr. “The town of Brookfield is 68 miles westerly of the metropolis of the Commonwealth and twenty from the shire town of the County of Worcester”). East Brookfield entry #22 miles 61, 62, 63; North Brookfield entry #23 most of mile 64; Brookfield entry #24 bit of mile 64, 65, 66, tiny bit of mile 67; West Brookfield entry #25 miles 67, 68, 69, part of mile 70. Distances of the UBPR through the towns that make up Brookfield: East Brookfield= 2.3 miles, North Brookfield= 0.6 miles, Brookfield= 2.5 miles, West Brookfield= 3.4 miles
Warren (Western: April 1795. Unknown Surveyor. “Plan of Western, County of Worcester; 73 miles from Boston State House and 24 from Worcester”). See entry #24 miles 70, 71 then need to flesh out from there. Distance of the UBPR through Warren= 6.0 miles.
Hampden County (before 1812 part of Hampshire County)
Brimfield (road skirts the northwestern edge of town and does not go through the center. December 22, 1794 Surveyed. Jonas Blodget. “The reputed distance from Brimfield to Boston 75 miles from said Brimfield to Northampton 34 miles”). The Boston road went through either Sturbridge or through Brookfield as there is a road to each from Brimfield center. Distance of the UBPR through Brimfield= 2.1 miles.
Palmer (May 1795. Admatha Blodgett surveyor. “The Town of Palmer in the County of Hampshire is 82 miles west of Boston and 22 miles southeast of Northampton.”) Distance of the UBPR through Palmer= 5.7 miles.
Monson (May 1795. Admatha Blodgett surveyor. “The town of Monson in the County of Hampshire is about 84 miles west of the town of Boston and about thirty miles southeast of Northampton.”) Distance of UBPR in Monson = about 2.3 miles. Note that the border between Palmer and Monson west of “Scott Bridge” across the Quaboag River is the Post Road, so technically the distance of the road is part of both towns, but I count it as Monson for purposes of these entries.
Wilbraham (May 22, 1795. Unknown Surveyor. “The town of Wilbraham in the County of Hampshire is 89 miles west of Boston and 22 miles from Northampton”). Note the Post road cuts across the north of town and the meeting house is somewhat south of the road. Distance of the UBPR through Wilbraham= 5.1 miles.
Springfield (May 20, 1795. Israel Chapin. “To Boston from the Meeting House 96½ measured miles. 20 miles from the Meeting House to Northampton”). Distance of the UBPR in Springfield= 6.5 miles
West Springfield, across the Connecticut River, was the last town in the state along the Upper Boston Post Road. The town later divided into the separate towns of West Springfield and Agawam. (May 20, 1795. Unknown Surveyor. “The Distance of the Center of the Town from Northampton is –18 miles–from Boston 100 Miles”). I will return to this town after I finish the entries between Worcester and Springfield when I begin the walk south to Hartford and New Haven.
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Distance traveled in this entry along the route of the Upper Boston Post Road: 0 miles.
Total Distance traveled thus far along the route of the Upper Boston Post Road from Worcester Courthouse to Springfield “Meeting House” (four entries): 4.3 miles.
Total Distance traveled along the original route of the road from the Old State House in Boston for this project: 51.0 miles.
Total Distance covered for all the walks described in Boston Rambles: 112.6 miles