Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

The Road to Harvard, Part 2


Roxbury Crossing. View of the Islamic Society of Boston Cultural Center on Malcolm X Boulevard near Columbus Avenue, 300 yards away from the the First Church of Roxbury, the original house of worship in Roxbury.

One of the difficulties in doing a project of this nature is the internal tension between a desire to produce these entries in a steady stream and the fear of making mistakes or of being superficial. I have an urge to generate as many entries as I can as quickly as possible. I also know that if the entries are not interesting to me or feel insufficiently researched I will keep them in the draft stage. However, if I wait until I have the perfect entry I fear none of these entries will ever see the light of day. The problem is twofold; I do not want to be wrong about anything and so I write fact-filled entries that can quickly become unwieldy. I risk losing the reader in a fog of detail although my intention at the start is usually to make a simple point. So it is with this particular walk: I want to keep researching and writing everything I can about anything of interest along the old road leading from Boston to Cambridge. As it is I am writing a second entry to cover the material I hoped to cover in the first entry because I became focused on a single aspect of the road.

The irony is that these initial entries are meant to be general walks through the city to set the table for entries that are more detailed about specific aspects of Boston: neighborhoods, population data, cultural essays, historical pieces on specific events or places, topical material that I want to try to embed in a political, cultural, and historical framework, and so on.

Therefore I have to force myself to write these entries without full possession of all the facts I would like to have. I have also deliberately held back some interesting facts to use in future entries to prevent the entries from becoming too long.  I cannot claim to know everything about the history I discuss or the cultural or political scene I comment upon. The most important thing I can do is to write something honestly and admit when I do not know something or admit when I am wrong about something. Thus the initial entries may appear, to me and perhaps to the reader, to be somewhat vague. It is my hope to go back to many of the places I write about in these general essays and spend more time researching the facts and filling in the details. If the reader wishes to help fill in details I am more than happy to accept comments and criticism; there is a comments section for people to leave positive or negative comments (please be reasonable), and I welcome constructive criticism.


The best way to overcome my penchant for excessive description is to walk the road with somebody else. Then I have to rein in the temptation to stop at every library or church or old building and keep a steady pace, filling in the facts as I go along. I recently walked this road twice in the company of another person and it has helped me immensely to focus on the central aspect of these walks: to lay down a frame which can support future entries.

This walk originates at the Parting Stone in Roxbury, a little short of three miles along the old road to Cambridge. The route heads right at the parting stone downhill to Roxbury Crossing,  follows Tremont Street from Roxbury Crossing up Mission Hill to Brigham Circle, then heads west on Huntington Avenue to Brookline, where it then follows Harvard Street in Brookline through Brookline Village and Coolidge Corner to Allston, passes through Allston (and Brighton? to be discussed in a future entry), crosses the Charles River over what is today the Larz Anderson Bridge, and follows JFK Street into Harvard Square, a total distance of about five miles. There are milestones at miles 4,5,6,7, and 8 but not at mile 3. Both the walks along Upper and Lower Road to Braintree as well as the Lower Post Road to Dedham also cover a distance of about five miles. The distances are unsurprisingly not linear and the location of milestone 8 of each of these walks is at varying distances from the State House as the crow flies. For instance the Lower Road to Braintree 8 mile marker is in the town of Milton, a little more than six miles from the origin if one followed a straight line. Similarly the 8 mile marker for the road to Dedham is in West Roxbury, about seven miles away from the State House in a direct line.

 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.

The 8 mile stone on the road to Cambridge, located inside the fence of the Old Burying Ground of the First Parish Church of Cambridge, is however only slightly more than 3 miles from Downtown Boston. This is a reflection of the extreme contortions the road takes and a reminder of the terrain of colonial Boston; the Back Bay was a “Bay,” the narrowest part of the Charles (and hence the easiest place to build a bridge) was at the crossing between Allston (or Little Cambridge as it was known in the colonial era) and Cambridge, and much of the terrain along the starboard side of the road through Brookline and Roxbury was salt marsh and tidal flats. The obverse side of the stone, which reads Cambridge New Bridge 2 1/4 miles 1794 reveals the dramatic changes which occurred after the Revolution. As the population of Boston expanded, the open spaces between Cambridge and Boston once ruled by nature were tamed as new bridges, turnpikes, streets and neighborhoods were built on the marshes and difficult terrain.


Obverse of the milestone in Cambridge, which reads Cambridge New Bridge 2 1/4 Miles 1794. The New Bridge, at the site of today’s Longfellow Bridge, shortened the travel distance from Boston to Harvard by 5 miles.

The changes to the landscape over time  explain the fact that the end of this five mile walk is almost the same distance from the Old State House as the beginning of the walk, as the road traces a sweeping arc around once impassable areas. It does not explain the fact that although the walk starts in what is now Boston, it passes through the town of Brookline, goes back into Boston in Allston-Brighton, and ends in the city of Cambridge. As I have previously explained (See the entry What is Boston), I consider Brookline, Cambridge and other towns in the Boston area to be part of the terrain that can be referred to as Boston for the purposes of these rambles. Indeed the population density of both Brookline (over 8000 people per square mile) and Cambridge (almost 13000 inhabitants per square mile) is greater than all but a handful of the 50 largest cities in America. Brookline and Cambridge remained outside the boundaries of Boston by choice as other areas such as Allston and Brighton chose to merge with the growing city in the nineteenth century and became neighborhoods rather than separate towns. This contrasts starkly with the current trend towards consolidation of towns and even whole counties in much of the Sun Belt, and goes a long way to explaining the ‘fact’ that Boston is not even among the 20 largest cities in the United States by population, but is clearly one of the 5 or 10 most important cities in the country by most measures. Again, a topic for future discussion.


Roxbury was one of the towns which chose to merge with Boston. In 1858 what was known as Lower Roxbury merged with Boston while the rest of Roxbury, including Jamaica Plain and West Roxbury, resisted the call for unification for a few more years. As I turn away from the First Church of Roxbury and head down the hill towards Roxbury Crossing MBTA station, I exchange the view of a traditional nineteenth century New England church spire for a view of a minaret. The role of religion in Boston is one of the themes I would like to investigate in future entries, and these spires are clear evidence of the changes over time that have occurred in Boston, a city founded by Puritans from England.

After passing the Islamic Cultural Center and Roxbury Community College, I cross Columbus Avenue and start uphill on Tremont Street. The MBTA station on the left, Roxbury Crossing, takes its name from the spot nearby where the road to Cambridge crossed the Stony Brook, a stream that has now been channeled underground, but which once ran along the entirety of what is now the Orange Line, Commuter Rail, and Amtrak rail tracks. As I climb Mission Hill the neighborhood becomes progressively more polished, particularly after passing the Mission Church near the top of the long incline. Indeed, by the time Brigham Circle is reached, there are restaurants, banks, a grocery store, and many Harvard related buildings lining the road on both sides, a far cry from 25 years ago when Mission Hill was notorious for crime, so much so that when a man shot his pregnant wife and then claimed it was an armed robber who had committed the deed, the police and most of the public initially bought the story. Again, as I pass each neighborhood, the temptation to linger and wander through time and space is strong, but I press on, vowing to return to discuss the area in more detail another day.

Plaque on Bridge over Route 9 connecting the Jamaicaway to the Riverway. Among the names on the plaque are James Michael Curley and Franklin Roosevelt.

Plaque on bridge over Route 9 connecting the Jamaicaway to the Riverway.  The old road crossed the Muddy River at this spot which today runs through a culvert under the road. Among the names on the plaque are James Michael Curley and Franklin Roosevelt.

The road to Cambridge swerved west here, following what is today Huntington Avenue, passing the four mile stone set into a wall on the right hand side of the street, and heading downhill to another crossing. What was once the Muddy River was landscaped in the nineteenth century by Frederick Law Olmsted into a part of the ‘Emerald Necklace’ of parks ringing the core of Boston. Passing under a bridge built during the Roosevelt administration, I enter the town of Brookline, a prosperous “suburb” of Boston. In truth it is difficult to tell we have left Boston as Brookline, particularly in the area through which we pass, is quite urban in feel. We head through busy Brookline Village along Harvard Street and arrive at even busier Coolidge Corner. Harvard Street and the cross streets such as Beacon Street are the main commercial streets of Brookline. Coolidge Corner has a mix of national chains (Trader Joes, Peets) and local businesses (Brookline Booksmith, one of the last of the independent booksellers left in the Boston area). Along the way we pass the five mile stone near Coolidge Corner. Brookline is an interesting town and deserves a lot of attention, but that will have to wait for another day, as there are still three miles to go.

The walk along Harvard Street in Brookline is always busy, but the restaurants and stores begin to decline in number as we approach the border with Allston. However, as soon as we cross back into Boston, the commercial activity reaches a crescendo, with many shops, bars and restaurants, as well as the large Herb Chambers automobile showrooms lining Commonwealth Avenue to the right (an area that has historically associated with automobile showrooms. Again, for another day). Brookline is a wealthy town, but Allston is less well off, and is primarily known in Boston as a “student ghetto.” There is also a large immigrant population in Allston, and much of the housing stock is composed of rental units in older, less well-appointed apartment buildings. The area around Harvard Avenue from Commonwealth Avenue past Beacon Street, to Cambridge Street is a bustling area which caters to the large local student and immigrant population. It is one of the most interesting neighborhoods in the city in my opinion and future entries will be devoted to analyzing the diversity of the area. Along Harvard Avenue in the midst of a chaotic, noisy, heavily-trafficked commercial stretch sits the six mile stone almost invisible amidst all the activity. So invisible is it that it was literally run over by a truck recently and had to be repaired and reinforced. This was merely the latest insult to a stone which had disappeared for many years and was only rediscovered and reset on Harvard Avenue sometime before World War II. My companion on a walk along this road is skeptical that this is a real stone and, after thinking it over, I am inclined to wonder myself, and hope to look more deeply into the ‘rediscovery’ of the stone and the circumstances surrounding its disappearance.


View of the Charles River from Larz Anderson Bridge from Allston into Cambridge. Weld Boat House in the foreground and various other buildings of Harvard University can be seen.

Another area of this road that deserves more research lies ahead as we approach Cambridge Street. Here the road and the neighborhood of Allston is split by the canyon of the Massachusetts Turnpike and the westward-bound rail tracks which originally brought cattle cars here from the hinterlands to the slaughter houses that supplied Boston with beef. Here the putative old road suddenly veers right onto Cambridge Street for about 800 yards over the Turnpike and the railroad tracks before turning sharply left onto North Harvard Street. A glance at the map will show that the logical direction of the road to Cambridge would have been to continue straight along what is now Franklin Street, which merges seamlessly with North Harvard Street just before Western Avenue. However, the seven mile stone is on North Harvard Street before the junction with Franklin Street. It is possible the stone was moved. It is also possible that there is a good reason the road snakes as it does. Alternatively it is possible that Franklin Street is the course of the original road. Another subject to investigate.

This section of Allston is more tranquil and primarily residential. Once we cross Western Avenue, however, we enter ‘Harvard Land’: Harvard Stadium, Harvard athletic facilities, and the buildings of Harvard Business School all line the street along the way to the Charles River. Crossing the river over the latest incarnation of the bridge that has been here in one form or another since 1663 we arrive in Cambridge, and pass many more Harvard buildings along JFK Street into Harvard Square. Along the way the restaurants and bars start to pick as we near bustling Harvard Square. Passing through Harvard Square we continue on a short distance past the First Parish Church until we are directly across the street from Cambridge Common, where our walk ends at the eight mile stone.

There is so much more to discuss about the sites (and sights) along this road. What is the difference between Allston and Brighton and why are they always discussed as one unit? What is the past, present, and future role of Harvard along this road? How did the neighborhoods evolve to become what they are today? Why is Brookline a separate town from Boston and what has it meant for the development of the area, particularly in terms of schools and real estate?  I also want to look at ethnic, class, and cultural diversity along this road, and look more carefully at the institutions and cultural artifacts along the way. More questions than answers: that is the point of these initial walks though, to set the table for future entries on a variety of topics.

1829 Road to Cambridge Detail (Hales)

Hales map of 1829: Note that Harvard Avenue/Street passes from Brookline into Brighton (it is the road heading north from ‘Dr Aspinwall’), then turns sharply right at the T in Brighton onto what is today Cambridge Street, before turning sharply left at the O in Brighton, onto what is today North Harvard Street in Allston, and finally turning sharply right again at what is today Western Avenue before crossing the river into Cambridge.

Addendum: I have inserted a detail of J.G. Hales 1829 map of Boston and Environs here. It shows that Franklin Street is unlikely to have been the original “Harvard Street” and that the snake that is Harvard, Cambridge, and North Harvard Street existed at least as far back as 1829.

3 Responses to The Road to Harvard, Part 2

  1. I enjoyed your post. I regularly follow this route on a run that follows the ride of William Dawes on the night of April 18, 1775. It is often referred to as the Roxbury Highway but I have yet to find a street by street description. I start at City Hall Plaza and run down Washington Street to Dudley Square. I turn onto Dudley Street and follow the same route you have indicated. The MA Turnpike wreaks havoc with the route as you’ve noted. I’ve read that Franklin Street was renamed and used to be the continuation of Harvard. I too have been puzzled by location of stone near the intersection of Franklin Street & N. Harvard and imagine it was relocated or the intersection has changed slightly.

    • Thanks for your comment. The Brighton “Zigzag problem” is a conundrum. I have looked at Hales’ 1829 map of Boston and Environs and it shows the zigzag very clearly; that is, it shows Harvard Street ending at Cambridge Street in Brighton then recommencing north from Cambridge Street a little further east at what is today North Harvard Street,then twisting right as it reaches what is today Western Avenue, so it is a route dating to at least 1829. Plus there is no sign of Franklin Street or any street that would putatively have been a more direct route eliminating the zigzag. So there must be another explanation for the twist of Harvard Street in Brighton. My latest hypothesis is that there was some type of wetland that the road passed around. I will look more carefully at older maps for clues to support this hypothesis. I will come back to this question in a future article on Brighton. I will also try to post Hales’ map somewhere on the site so you can take a look. It is also viewable at the BPL’s Leventhal Map Collection.

      • Interesting. I have noted that Franklin Street does not join Harvard on other pre-Turnpike maps Such as the 1859 Walling map but the railroad runs through. The 1829 is pre-railroad? This zig-zag is intriguing!


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