Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

The Road to Braintree

Eustis Street Firehouse, near the beginning of the Lower Road to Dorchester. Now the home of Historic Boston, Inc., which has a nice description of the history of the building here

 Dudley Square, Roxbury, Massachusetts.

I moved to Braintree, Massachusetts in February 1977 from the semitropical island of Bermuda. I had never seen snow and the ground in Braintree was covered in it. Lots of it. Also it was extremely cold, something for which I was completely unprepared. Also, as a teenager moving to a new town, indeed a new country, I hated it, but that is a story for another day. As a juvenile I had no say in the matter, and for better or worse, it became my home, the place I went to high school, the place I met my wife, and the place my family lived until the early 1990s. I rarely visit anymore, despite the mere 11 miles between my house and Braintree Town Hall. Except for a few vestigial links, I have almost no connection to the town in which I spent my high school years, becoming an American.

Braintree is a typical small (c. 36,000 inhabitants) suburban town outside Boston, the most important point of interest probably being the South Shore Plaza. However, it often seems to appear on my radar screen at curious times. Usually it is for unwanted reasons, a mass shooting by a former resident of the town, for example. More recently, a mobile payment company by that name has become prominent in the media.  So too, did Braintree appear unexpectedly to me in the middle of Roxbury as I contemplated an old map of the route I planned to walk. The route is the so-called ‘Lower Road to Braintree’.

As the image I have of Braintree is of the somewhat modest town of today, it is often confusing to see roads on old maps referred to as the “Road to Braintree,” as it implies that this was an important destination in colonial Massachusetts. The Braintree of John Adams, however, originally included today’s Quincy as well, and it is to this part of “Braintree” that these maps refer. Indeed, Braintree today is the result of a bifurcation of the original town in which the more rural portion of the town ended up with the original name of the whole. It would be as if the area that would become Kentucky took the name of its original parent Virginia, and the original state took the name of a famous son of the state (the state of Jefferson or Madison?) But I digress. Such is the nature of these ‘rambles’.

Dudley Square Roxbury

View of Dudley Square, Roxbury, from the intersection of Washington Street and Eustis Street. In Colonial Roxbury, this would have been the main thoroughfare in and out of the town of Boston

Standing on the unprepossessing corner of Washington Street and Eustis Street on a warm summer morning it is hard to imagine that in the colonial era this would have been the first crossroad along the sole road leading into and out of Boston. As I mentioned in earlier entries, The town of Boston consisted solely of the land on a peninsula jutting into Boston Harbor connected to the mainland by a narrow “neck” which opened out at this point in what was then the separate town of Roxbury. From Dudley Square the possible number of routes multiplied. I have described the roads leading to Cambridge and to Dedham in previous entries. Today I want to continue to fill in the “skeletal” structure of Boston by describing a third road, the original road that the traveler of say, 1640, might take to get from Boston to Dorchester and on to… yes, Braintree.

Detail of 1831 Map of Dorchester by Baker

Click to enlarge. Detail of 1831 Map of Dorchester by surveyor Edmund J. Baker This map shows the three roads into Dorchester from Boston at the time. The first two emanated from Dudley Square, and correspond to the Upper and Lower Road to Braintree. A fragment of the Upper Road can be seen at the far left (marked by the number 3). The Lower Road (subject of today’s walk) is the road passing between the letters U and R (also marked by the number 3, corresponding to the distance from the State House in Boston). This road passes over the border between Roxbury and Dorchester, the so-called Roxbury Brook (just below the letter R).  The third road can be seen coming from the top right (above the B in Boston) over the marshy area of the so-called “Boston Bay”(most of the water and marshy areas have been filled in but the “Bay”still clings to life as the Fort Point Channel).  This much straighter road is a turnpike built around 1806 to shorten the distance from Boston, and corresponds to today’s Dorchester Avenue.

Maps from as late as 1831 show that there were only three roads from Boston leading to Dorchester, of which two required a trip through Dudley Square. The third was a turnpike constructed in the first decade of the nineteenth century which is know today as Dorchester Avenue.  The two roads from Dudley Square consisted of the “original” road to Dorchester, which was termed the “Lower Way, or Road” and the “Upper Road” which was constructed in the mid-17th century and is roughly today’s Warren Street in Roxbury and Washington Street in Dorchester.  I will describe my walks along the “turnpike” and the “Upper Road” in future entries.

This entry is a walk along the original road from Boston through Dorchester, which today follows Eustis Street (see map) and then Dudley Street in Roxbury to Upham’s Corner in Dorchester, then continues onto Hancock Street to Bowdoin Street, turning onto Adams Street which passes through Field’s Corner and Adams Village, briefly onto Gallivan Boulevard, then back onto Adams Street to the bridge at Lower Mills.  This is not only the original road to Braintree (now Quincy and Braintree), but also to Plymouth, and the entire South Shore. The distance from the entrance to the Eustis Street Burying Ground to the bridge at Lower Mills is 5.2 miles.

First mention of the road is to be found in the Dorchester Record Book in  November, 1634 which recorded that “a sufficient cart-way be made to the mill at Naponset at the common chardge, if the chardge exceed not above five pounds.” (History of the Town of Dorchester (1859), Ebeneezer Clapp, p. 34)  This road has therefore existed, in one form or another, for nearly four centuries. Surely it qualifies as one of the oldest extant roads in the United States. It passes through the northeastern corner of Roxbury and then traverses the length of Dorchester, the largest neighborhood in the city of Boston, before reaching the bridge over the Neponset River at Lower Mills, where it enters the town of Milton on the way to what is today Quincy. This entry describes the state of the road as I saw it from this corner in Roxbury to the bridge at Lower Mills. In future I will examine specific aspects of the road and the neighborhoods through which it passes, but the remainder of this entry is composed of observations about the road I walked.


Invariably the first thing that happens on one of these transects through the city is the dissolution of whatever preconceptions I had about my anticipated experience. There is always something unanticipated that is almost always delightfully unique and the anticipated negative interactions almost never occur. Indeed this walk is no different from the rest in that regard, as only a few steps along Eustis Street in Roxbury I come across a beautifully restored nineteenth century red brick firehouse with a large sign reading Torrent Six (see image at the beginning of this entry). I had anticipated an endless sea of urban blight along this walk and my expectations were mostly (though not entirely) unfounded. Along Eustis Street there has clearly been a lot of urban renewal, of a quality much superior to the massive soulless housing projects of yore. Smaller, cheerier units of housing line these few blocks where I imagine a few years ago stood either empty warehouses and shuttered businesses or empty lots. Indeed it does not take much imagination to visualize what things might have looked like, for the view down Harrison Avenue in either direction reveals exactly the dilapidated buildings I had pictured lining this route.

I don’t want to portray this area of Roxbury as some hidden version of the Back Bay: It is not. It is a neighborhood that was once modestly prosperous and possesses some interesting architecture that reflects its former higher station, but on the whole it is depressed economically, has very few services of the type most people living in other parts of Boston take for granted. There is no large grocery store chain, but there are small groceries here and there and a larger Tropical Foods grocery store on Melnea Cass Boulevard and Washington Street, as well as another low cost chain in Uphams Corner. There is but one restaurant that is worthy of a review between the starting point of my walk and Uphams Corner, a distance of 1.5 miles. There are none of the small boutiques or quirky shops one finds in Jamaica Plain or Somerville. There is a jagged, uneven quality to many of the areas through which I walk, like a beautiful stained glass window which has lost a large fraction of the original intricately designed and beautifully colored panes, replaced by a piece of cardboard, or plastic, or nothing. There are, however, still some intact panes and the frame is still holding up after four centuries of weathering.

This road is four centuries old and there are layers of history overlaid with an incredible diversity of culture that one finds only in a walk through a large and complicated city such as Boston. Over the course of a five mile walk I first pass through a largely black neighborhood comprised of both African Americans and immigrants from Jamaica, Haiti and most likely every other island in the Caribbean, then a predominantly Dominican and Puerto Rican neighborhood, a Cape Verdean neighborhood, a predominantly Vietnamese neighborhood, and a classic Irish Boston neighborhood, with a lot of smaller pockets of diversity mixed in and one or two ‘characters’ sprinkled in the mix who are probably from another planet. On top of that throw in some surprisingly diverse landscapes, lush green hills with views of the ocean, a lovely river with a waterfall, and salt marshes. Try seeing all that on the Appalachian Trail! And it doesn’t cost a penny to walk from one end to the other. Perhaps the reader can see why these walks appeal to me.


Mural Dudley Street. Unity Through Diversity- I could have saved the reader a lot of trouble by just posting this image and writing nothing else.

I continue down Eustis, turn right for a a few yards on Dearborn Street, and then left again onto Dudley Street, which continues to Upham’s Corner (apostrophe or no? a question for another day!) The neighborhood transforms fairly quickly to a predominantly Spanish-speaking area, and shortly thereafter I start to see evidence of the sizable Cape Verdean community (see photos).  I pass the beautiful Shirley-Eustis House, pass the newly rebuilt Upham’s Corner Commuter Rail Station and quickly arrive in the eponymous neighborhood, marked by the presence of two especially prominent features, the Strand Theatre and the Dorchester North Burying Ground.


The First Parish Church of Dorchester, in what has been generously described as the “troubled neighborhood of Bowdoin-Geneva.” A beautiful place which confounds the standard image of the “inner city.”


Fishing for souls in whatever language works

Continuing on through Upham’s I turn down Hancock Street, which I follow to a tangle of intersecting streets, the surest sign I am in Boston and that these are old roads. I turn briefly onto Bowdoin Street, then left around the base of Meeting House Hill, upon the summit of which sits the First Church of Dorchester, a striking ‘classically-New England’ church, one in a series of churches serving the settlers of Dorchester since 1630. Across the park from the Meeting House is St Peter’s Parish Church, a large neo-Gothic Catholic church from 1872, the two churches eloquent testimony to the evolution of the neighborhood over four centuries.

I continue on Adams Street, which I follow all the way to Lower Mills. Along the way I pass through Field’s Corner, notable for the presence of a significant Vietnamese population. Crossing Dorchester Avenue (the aforementioned Turnpike) Adams Street twists and turns, avoiding the steep inclines of Ashmont Hill and Pope’s Hill, past a used car dealer and neighborhoods of remarkably diverse housing, many of the triple deckers for which Dorchester is famous, but also large Victorian mansions and brick apartment buildings. After negotiating the pass between the hills, the road descends sharply as it enters the Neponset River Valley.  The change in topography along the route is only truly appreciated by those who walk. I have driven through here countless times but only today do I realize that the whole area around the Dorchester/Quincy/Milton line is a river valley and tidal estuary.

Adam's Village in Neponset is primarily an Irish neighborhood, in case this photo is too subtle.

In case this photo is too subtle, I should point out that Adam’s Village in Neponset is primarily an Irish neighborhood.

Passing through Adam’s Village (I never really knew what to call this intersection of Adams Street and Gallivan Boulevard although I have always had a sense that it was an Irish neighborhood -see photo below), I briefly follow Gallivan Boulevard, crossing over to return to Adams street which winds past Cedar Grove Cemetery and has views over the Neponset River estuary. I pass over the Mattapan Trolley line, and wind down towards Lower Mills, passing a milestone from 1734 indicating 7 Miles to Boston, a reminder that this still the old road into town.

Milestone with the caption "7 Miles to Boston Townhouse 1734"

Milestone with the caption “7 Miles to Boston Townhouse 1734”

Soon I arrive at the lovely little village of Lower Mills, so named for the mill set up in the 1630s by Israel Stoughton. Mills were traditionally set up at waterfalls to take advantage of the water power, and the falls here represent the first ones up the Neponset River, hence Lower as opposed to ones further up the river. The falls usually mark a narrowing of a river and these falls are no different: hence the first bridge over the Neponset River was built here and explains the winding route originally taken to get to Braintree. The Neponset River marks the boundary between Boston and Milton and is a good place to stop. I will continue on to Quincy another day, and hope to tease the reader back with the promise of many milestones and fascinating landscapes, architecture, and history.

If the description of this walk seems rushed and superficial, that is because it is: the rich architectural, historical, cultural, and even natural landscape of a walk of only 5+ miles demonstrates to me the validity of this enterprise. I plan to return time and again to parts of this walk to focus on specific aspects: Vietnamese culture in Boston, nineteenth century bank buildings, murals, the role of religion, politics etc. This entry is merely a modest transect across a wide spectrum of possibilities.

Neponset River at Lower Mills, with mill buildings, mostly restored as housing. Is this really Boston or is it a town in the Berkshires?

Neponset River at Lower Mills, with mill buildings, mostly restored as housing. Is this really Boston or is it a town in the Berkshires?

One Response to The Road to Braintree

  1. That last photo does look like the Saw Mill in Montague.


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