Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

The Upper Post Road Milestones (WTPR#14)

 Milestone indicating 8 miles to Boston, 1734, bearing the initials AI which stands for Alexander Ireland, a surveyor. Removed to a place inside the fence of the First Parish Cemetery, Cambridge, in 1892, it is located near the grave of the man whose initials it bears.

Milestone indicating 8 miles to Boston, 1734, bearing the initials AI which stands for Alexander Ireland, a surveyor. Removed to a place inside the fence of the First Parish Cemetery, Cambridge, in 1892, it is located near the grave of the man whose initials it bears. This is the only stone in this series that is NOT a Paul Dudley stone.

“He was buried in the tomb of his fathers; but his epitaphs are only to be read on the numerous mile-stones that skirt the roads…”

Nathaniel B. Shurtleff, in History of Norfolk County, referring to Paul Dudley.

One more entry (#14) from my Walking the Post Road Project. The purpose of these entries is to lay a foundation for the project. My intention is to start with Boston as a blank slate. As I discussed in a previous entry, political borders are irrelevant to my definition of Boston (What is Boston?), so I am using a different approach to create a personal definition of Boston. Onto a basic topographical map of the Boston area I want to add layers of complexity in order to be able to examine different aspects of Boston from different perspectives, as will become apparent as the project evolves.

To make things easier for me, I think of this project as a human being, which I will call Boston Man. To the blank map (an entry on the topography and geology of the Boston area will appear in the near future) I begin by constructing a skeletal framework. The first of these are the entries I have previously produced for my Post Road project. As the reader may have noticed, they have remained mostly unchanged, barring some small corrections. Here and there I have appended editorial comments in order either to update some information or to indicate that a subject in the entry will be pursued at a later date. But I want to keep these entries in their original form as they were the starting point for most of the recent walking projects I have done.

The original entries followed the original road into and out of the town of Boston during the Colonial period. I have already discussed the original road out of Boston to Roxbury (Transitions, Boston Neck: No Man’s Land). This part to me is the spinal column (or Axial Skeleton to use a more scientific term). Once the road reached what is today Dudley Square in Roxbury, it split into at least 4 roads, one heading southwest and one north, and 2 heading south. The roads heading southwest and north are respectively the road to Dedham (or the Lower Post Road) and the road to Cambridge (the Upper Post Road). The roads heading south are the Upper and Lower Road to Braintree, leading eventually to Plymouth and other points south of Boston. I think of these roads as the bones making up the arms and legs of my hypothetical Boston Man (or the Appendicular Skeleton). I covered the road to the junction between the road to Dedham and the road to Cambridge in a previous entry (Deviating from the Straight Path), and I discussed the connecting tissue for all the original roads in another entry (Milestones). One of the “limbs,” the road to Dedham, is the route of the Post Road I followed to New York. There are five more entries from that project covering the road from Roxbury, through Jamaica Plain, Roslindale, and West Roxbury. I will add these in the near future as well, again mostly unchanged, with perhaps a few editorial comments.

In the near future I will add entries discussing the two “limbs” heading south out of Roxbury. These were not part of the Post Road and so will be the first de novo entries which will appear and will mark the official “start” of the walks which will make up the core of this project. The entry below is a slightly updated version of Entry 14 in the Post Road project, originally published June 16, 2010, which followed the route of the Upper Post Road as far as Harvard Square in Cambridge.

Once the basic “skeleton” has been constructed, I want to continue to construct a more complete skeletal system, consisting of bones, cartilage, ligaments, and tendons. These will be the roads that were added to the city as it developed: turnpikes, streets of newly created neighborhoods, bridges, highways, as well as the original roads that made up the town of Boston and the surrounding area.

The skeletal system is the way I can create a map of the city from which I can then begin to add other systems such as the circulatory system or the nervous system.  My aim is to walk along roads or through neighborhoods and write a “tour” which will consist of a topic relevant to that particular walk. These will be topics ranging from history to the demographic makeup of Boston to politics, to just about anything that I find interesting, in truth. Hence the title of the project, Boston Rambles. This is hopefully where the true nature of this project will begin to become clear. This project aims to create a body of work, organized by the relevant topic (each one is a ‘system’ in my hypothetical Boston Man), which, in sum, creates a complex, dynamic, and interactive image of the city. It is my intention that the walks can be followed by anybody and, to that end, I intend eventually to design these to be podcasts that can be followed using a personal mobile device.

Finally, a quick explanation/apology for the slow progress of this project. The process of transferring these entries from my previous project involves changing the format from iWeb, a now discontinued service from Apple [the shine is off the Apple!], to WordPress. Getting the photos, images, maps and text right is time-consuming and tedious, so this has been a slow process. Please bear with me as I work through this slight hurdle. Also, it is bird migration season as well as garden season, so I have been slightly distracted from this project with these other pursuits. Originally Published Wednesday, June 16, 2010.


In a previous entry I mentioned that the Post Road from Boston split at the Parting Stone in Eliot Square, Roxbury. I have been following the road to Providence, but there was another road which led to Cambridge. There is a series of milestones along the route from Roxbury to Cambridge so I took the opportunity of a nice afternoon to walk what was known as the Upper Post Road from Roxbury to Harvard Square in Cambridge. (Another note: I recently had the pleasure of walking this route with my good friend Dave E. In the near future I will publish an updated and more detailed version of this walk)

The map below indicates the milestones (blue place marks) and the route I followed through Mission Hill in Boston, then Brookline, then back into the Allston neighborhood of Boston, across the Charles River to Cambridge, ending at the First Parish Church Cemetery just outside of Harvard Square.

Directly below is a map from Stephen Jenkins’ 1913 edition of The Old Boston Post Road. As you can see, there are three routes which are referred to as “Post Roads.”  The one I am following for this project is known as the “Lower Post Road,” and passes through Rhode Island and along the Connecticut coast. There is a second road which also leaves from Dedham, passes through Medfield, and heads toward Hartford through northeastern Connecticut. This is known as the “Middle Post Road.” Finally, leaving the Parting Stone in Roxbury and passing through Cambridge, then west across Massachusetts on what is now US route 20 to Springfield is the “Upper Post Road.” This road then meets up with the “Middle” road in Hartford by following the Connecticut River south, then the two roads meet the “Lower” road at New Haven, where the three roads merge and continue on to New York.

Post Road Map from Stephen Jenkins 1913 book.

Post Road Map from Stephen Jenkins 1913 book. Click for better resolution.

Below the maps are photographs I took of each milestone, with the exception of the eight mile marker, which is in the photograph at the beginning of the entry.

Milestone 4, Huntington Avenue, near South Huntington intersection.

Milestone 4, Huntington Avenue, near South Huntington intersection.

The Upper Post Road has received the lion’s share of attention over the years. I believe this can be attributed to a number of factors. Of primary significance is that any story of the Post Road invariably starts with the near mythical first ride in 1673 from New York to Boston, which followed the route through Hartford and Springfield. What is seldom mentioned is that this service was almost immediately halted during King Philip’s War and was not resumed until the 1690s, or that there was more than one postal route from New York to Boston. It messes up the continuity of the story to bring in more routes and riders. A second factor is that US Route 20 is called the Boston Post Road in most of the towns through which it passes, while the road south of Boston is variably referred to as the Old Bay Road, the Old Roebuck Road, The Providence Road, and other names. This is actually a result of the fact that it was a road of some importance BEFORE it became a Post Road, not that it is not the Post Road. A third factor is the presence of a milestone prominently displayed in close proximity to the gate of America’s most prestigious center of higher learning. The presence of this stone must have fired the imagination of countless students and professors at Harvard as they passed it on their way into Harvard Square, especially in the nineteenth century, when it stood just north of the Class of 1875 Gate. Contrast the prominence of the route passing through Harvard Square with that of the lonely road out to West Roxbury, and it makes the Lower Post Road almost seem like Charlie Brown’s Christmas Tree.

Milestone 5, Harvard Avenue, Brookline, near Coolidge Corner

Milestone 5, Harvard Avenue, Brookline, near Coolidge Corner

I have chosen to follow the Lower Post Road for a number of reasons. Primarily, the route seems more interesting to me, passing through Providence, Newport, New London, and other towns of importance in colonial America. Secondly, a milestone caught my eye in the same way it might have caught the eye of the aspiring academics across the river from Boston, only the stone near my house is associated with the Lower Post Road rather than the Upper Post Road. Another reason is my interest in retracing the steps of the earliest travelers, the Indians who inhabited this area for thousands of years before the arrival of Europeans; the path I am following is explicitly mentioned in many early accounts of the European settlers as an important path from Massachusetts Bay to Narragansett Bay. Most importantly for me are the fascinating records of the journeys of two remarkable people, Sarah Kemble Knight and Alexander Hamilton. Both of these early travelers, as well as a number of other people who also kept diaries of their journeys, followed the Lower Post Road on their way to and from Boston.

Milestone 6, Harvard Avenue, Allston

Milestone 6, Harvard Avenue, Allston

Milestone 7, Allston

Some day in the future I will follow the other roads, but for now I am content to travel on the Lower Post Road. This post and another to follow in the near future describing the remaining milestones in Boston are fun detours which allow me to wile away a pleasant summer afternoon in the city.

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