Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Taking the High Road in Roxbury and Dorchester

Dudley Square, Roxbury. View from Warren Street (the 'Upper Road to Dorchester') looking back across Dudley Street towards Boston.

Dudley Square, Roxbury. View from Warren Street (the ‘Upper Road to Dorchester’) looking back across Dudley Street towards Boston.

The Last of the ‘Old Roads’ from Boston is the road variously referred to as ‘The Way to Braintree’ or the ‘Upper Road to Dorchester.’ It is the last in the sense that the road was laid out in the 1660s to provide a shorter route to the bridge over the Neponset River at what is today’s Lower Mills in Dorchester. The original route to Braintree, which I wrote about in a previous entry (The Road to Braintree), left today’s Dudley Square area along Eustis and Dudley Streets in Roxbury into Dorchester, passing through Upham’s Corner and Field’s Corner, then continuing along Adams Street following the path of least resistance by avoiding the hills of Roxbury and Dorchester.  The new road also began in Dudley Square but followed a route along higher ground along what is today Warren Street in Roxbury to what is today Blue Hill Avenue. After crossing Blue Hill Avenue the road continued along what is now Washington Street through Dorchester until the bridge at Lower Mills was reached. Today’s walk along this ‘new’ road is about 4.6 miles in length, whereas the ‘Lower Road’ via Eustis, Dudley, Hancock, and Adams Street distance is about 5.2 miles, thus saving 0.6 miles walking, a significant distance to somebody trying to get to church on a Sunday in winter or to the market laden with produce.

The real start of the walk is a few steps away from the Eliot Burying Ground at the  Haley House Bakery Cafe, a most pleasant way to begin a day’s walk. I love the food here, I love the atmosphere, I love the mission. Click the link and see what they are all about: they say it much more eloquently than I can. Haley House is a lovely oasis in what remains a challenging neighborhood. Let’s talk about the elephant in the room before I begin my walk. I can’t get around the fact that today’s walk passes through many of the poorest neighborhoods in Boston. In my experience the stereotypes and the cliches about Roxbury and Dorchester are inaccurate. There is undoubtedly more crime in these areas than in other parts of the city, but as I will discuss in a future entry, much of the violence that gives these neighborhoods a bad reputation is mostly young men feuding with other young men. I have never personally felt threatened in 25 years of walking, teaching, golfing, birding, shopping, or eating in any part of the city, Roxbury and Dorchester included. Rather than fear, I often feel strange because it is obvious that many people go out of their way to be nice to me because I so clearly don’t belong. More people greet me with a smile and are polite to me along the route today than the sum of all the times I have been acknowledged in all the years I have walked along Harvard Street in Brookline. I have had queries about whether I needed directions. On this particular day, a pickup truck actually pulled over along Warren Street and the driver asked if I was from around here. I confirmed I was from Boston and the gentleman commented that he “thought I might be a tourist from Kansas or somewhere who got lost”. Once I ran into the mother of a former student of mine who was so obviously puzzled by my presence in her neighborhood on a Sunday afternoon that she asked me awkwardly if I was going to a special art exhibit or something because basically, why else would I be here?


Map of Wards and Precincts of Boston. The pink line represents the route of the walk discussed in this entry. You can also click here for a more detailed map of the route.

Here is some data to put what I have been saying into perspective. Using data from the 2010 census and maps of the wards and precincts of Boston, I have determined that this walk passes through 26 of the 254 precincts in Boston, about 10% of the total. As this is a very old road, it is not surprising that it often forms the boundary between two precincts, and I count both precincts as part of the walk under the assumption that the boundary runs down the middle of the road. In a very cumbersome chart, which I have put into the following entry, the data show that, with the exception of the first and the last precinct of this route, the population that resides in the precincts along this route is predominantly not ‘White’, one of the terms of racial self-identification on the Census. Excluding Ward 9, Precinct 4, which is the first precinct of the route and has a significant portion of its area made up of parts of Northeastern University, and Ward 17, Precinct 13, the end of the walk, which comprises the area around Lower Mills, the White population of the route is only about 1% of the total White population of Boston. On the other hand, the Black population along this route makes up more than a quarter of the entire Black population of Boston, and nearly 10% of the Black population of the entire state of Massachusetts. Whether I want to admit it or not, this data has a face, and it is something I definitely notice as I make my way along the old road, much as I am sure my face does not go unnoticed as I wander through Roxbury and Dorchester, notebook in hand, gawking like the tourist I essentially have become in my own city.

I do not deny that the areas through which the road passes have real problems and need a lot of attention which I hope to discuss in more detail in future entries. However, I also want to go beyond the headlines to learn more and to write about contemporary culture in all of the neighborhoods of the city, including the areas through which this road passes. Another objective is to explore the history of these neighborhoods, and to try to discover what remains of the past. Overall, it is my hope to convey in these essays a more nuanced view of all of the neighborhoods, to try to understand how and why Boston developed into what it is today. A walk along this three century old road, which cuts through the heart of Roxbury and Dorchester,  is a way to begin to layer what was onto what is.


Dudley Square is always busy, always seems to be under construction, and always seems to stay the same. As this is the oldest area of Roxbury and hence has a long and complicated history I plan to write a separate entry in which I will walk around Dudley Square itself.  I leave the busy center of Roxbury along  Warren Street which did not receive its current name until 1825, when the town of Roxbury implemented a plan to name “all of the existing roads, to the number of forty.”¹ Previously referred to as the “Way to Braintree” or the “Upper Road to Dorchester,” Warren Street took the name of one of Roxbury’s most illustrious citizens, Dr. Joseph Warren, a casualty of the Battle of Bunker Hill on June 17, 1775, and the most important figure from the American Revolution you have never heard of.  The school at which he both attended and taught, Roxbury Latin, which long ago decamped to greener pastures in West Roxbury along with a statue of Joseph Warren which once stood prominently in a triangle that has since been removed at the intersection of Warren and Regent Streets (more on this topic another day), was located from 1853 until 1927 just off of Warren Street on the left hand side as we cross Dudley Street.

Warren House. Built by John C Warren in 1846 upon the site of the original Warren mansion of 1720.

Warren House. Built by John C Warren in 1846 upon the site of the original Warren mansion of 1720.

Not coincidentally, the land  on the left side of Warren Street was originally the Warren estate of about seven acres which extended from about Warren Place to Moreland Street as we head uphill out of ‘downtown’ Roxbury.  Maps of Roxbury from the 1930s show a house built by John Collins Warren, a prominent surgeon, the nephew of Joseph Warren, and the son of John Warren, a founder of Harvard Medical. I had not expected to find the house, as much of the area has undergone ‘urban renewal’, but it is still there, although currently empty and advertising for tenants to use the building as office space. A gentleman doing some repairs kindly gave me free rein to wander and I was amazed at how much of the original detail remains, including a large fireplace and a beautiful staircase. Outside on the front walls are engraved granite markers embedded in the stone Ruskinian Gothic Mansion which give us facts about Joseph Warren and explain that “the original house being in ruins, this house was built by Dr. John C. Warren in 1846.” In addition to building this house, Dr. John C. Warren served as the first Dean of Harvard Medical School, was a founder of the New England Journal of Medicine, was a founding member of the Massachusetts General Hospital, and in the same year he had this house built, 1846, performed the famous first surgery using ether as an anesthetic at the aforementioned Hospital in the surgical amphitheater now referred to as the Ether Dome. He also left his astonishing anatomical collection to Harvard which became the foundation for the fascinating Warren Anatomical Museum. Those old Boston Brahmins sure kept busy.

As a main artery out of Roxbury, Warren Street has undergone many changes; the street was widened in 1798 and again in 1872. However, the 1960s marked a new level of “street improvement,” the results of which can be seen today. The prominent feature of this stretch of road is not what is present but what is absent. A map of the area from 1931 shows not only a large number of residential buildings, but also the ‘New Jerusalem’ church and the Hotel Warren. Many of these buildings were demolished in the 1960s. I will discuss this at a later date but I will say here that, in my opinion, German or Japanese bombers could not have done as much damage to the city as did the “Urban Renewal Experts” of the period following World War II.

Detail of an apartment building called the Hotel Harold and Maud. Is the movie somehow a reference to this or is it a coincidence?

Detail of an apartment building called the Hotel Harold and Maud. Is the movie somehow a reference to this or is it a coincidence?

As I reach Montrose Street I am in the area where the third milestone along this road would have been. Samuel Abbot Green presented a paper at the Massachusetts Historical Society in 1909 on the subject of milestones in Boston. In this presentation he states “the third mile-stone on this road is now missing , though it was in place twenty years ago.”² My hope is to return to each of the milestones in turn and try to find source material in order to ascertain the provenance of each stone and the fate of each stone.

Four Miles to Boston along the Upper Road. Milestone from 1735 placed by Paul Dudley.

Four Miles to Boston along the Upper Road. Milestone from 1735 placed by Paul Dudley.

Fortunately Milestone Four still exists a mile further on in roughly the spot it has been located since 1735. The last mile of Warren Street leading to the stone is an improvement on the first section. After passing the Church of God of Prophecy, which is clearly an old theater (The Warren Theater, according to a 1931 map of the neighborhood), Warren Street becomes much more pleasant, with nineteenth century brick buildings lining one side of the street and a couple of lovely churches as well as Boston Latin Academy, one of the city’s exam schools. Many of the buildings along this part of the street are substantial nineteenth century mansions and brick apartment buildings that all need some renovation to bring back their faded glory. One fantastic street called Elm Hill Park consists of a cul-de-sac with lovely houses lining a central garden, and these houses would probably go for very large sums of money were they in my neighborhood. As most people’s wealth is tied up in the property they own, this seems to be yet another disparity between this neighborhood and other neighborhoods in the city. However, the topic of wealth disparity will also have to wait for another day.

Warren Street ends as it intersects Blue Hill Avenue, which I follow for about 200 yards before reaching Washington Street. Milestone Four, the main feature of note here, is another in the series of stones placed by Paul Dudley, Chief Justice of the Massachusetts Superior Court in the mid-eighteenth century, a person I have discussed in a previous entry (“Milestones”).  Today it sits on the short stretch of Blue Hill Avenue between Warren Street and Washington Street, in front of a Caribbean restaurant called Flames in an area known as Grove Hall, in Roxbury. I have inflamed a controversy by claiming that Grove Hall is in Roxbury but the fact is that old maps clearly show the original estate for which the area is named in Roxbury. Perhaps today the Dorchester line has migrated to Blue Hill Avenue, but on old maps all of the old ‘Brush Hill Turnpike’ in this area was within the limits of Roxbury and Dorchester only began a few yards down Washington Street. I ask a gentleman sitting outside of Mattapan’s Finest Barber Shop (to make matters even more confusing) what neighborhood he thinks he is in and he says Dorchester but he knows that many others will say Roxbury. To be continued…

Regardless of the location of the boundary between Roxbury and Dorchester, by the time I reach the intersection of Columbia Road and Washington Street I am certainly in Dorchester. If you are puzzled by the unexpected appearance of Washington Street, fear not. I was long confused by the seeming incompetence of town elders of yore who seemed to delight in calling numerous Boston streets Washington Street until I learned that most of the neighborhoods of Boston once existed as separate towns and so each town had its own Washington Street, the name of the street remaining as a vestigial relic of the former autonomy of these neighborhoods. Unfortunately for users of Google Maps this can lead to some curious driving directions.

As I turn down Washington Street from Blue Hill Avenue I pass Nation of Islam Muhammad’s Mosque #11, in a refurbished former funeral parlor. Interestingly, the address on the Mosque #11 website says ‘Grove Hall, Dorchester’. Strange as it sounds, I have a tangential connection to this place. Minister Louis Farrakhan, the Head of the Nation of Islam, was raised in Roxbury and was at one time minister of Mosque #11. Although born in New York City, he claims, in a speech given in Bermuda in 2009, to have lived a short while in Bermuda, the place I lived as a child, the place my mother grew up and lives, the place my aunt and uncle and cousins live, and the place where my grandfather is buried. Farrakhan specifically said that Bermuda is the place where ” my mother grew up, where my grandmother and grandfather are buried, and where my uncle, cousins…(live).” As it is a tiny island, it is not a stretch to say that it is possible that we may be related.

The atmosphere on Washington Street is much busier, and feels more urban and dense, quite different from the relative tranquility of the latter half of Warren Street. Beyond the Prince Hall Masonic Lodge I pass a number of large redbrick apartment blocks, the Jeremiah Burke High School, and the Holy Tabernacle Choir at the intersection with Columbia Road, a very wide and busy street. Crossing Columbia Road I pass a commuter rail station (the only rail service I encounter on the entire walk, until Milton!). The road passes along the base of Mount Bowdoin; I am very curious about the neighborhood up on the hill but I must push on.


House at 389 Washington Street, Dorchester

As I head into Codman Square, just before Algonquin Street, I pass a very large white mansion, which commands a great view over Dorchester and Dorchester Bay. From here the road descends gently to School Street, the approximate site of the missing Five Milestone. The missing milestones are a metaphor for much of Roxbury and Dorchester that is missing. A few of the old houses remain, some in great shape. Many need extensive renovation, a few seem beyond repair, and many have been torn down and replaced by empty lots, or with uninspiring modern buildings.

The service infrastructure along the route is not great. There are only a few shops and one or two grocery stores such as America’s Food Basket, but I begin to understand the term ‘food desert.’ Since I left Dudley Square I have found no restaurants along the lines of Haley House Cafe. There are lots of takeout restaurants, primarily Caribbean, Chinese, and pizza joints, more than one McDonald’s, and little else. I have lunch at one of these places, Tex’s BBQ, in Codman Square. The menu is varied, ranging from pizzas and subs, to burgers and ribs.  The person running the show is a friendly Greek woman who, when queried, claims to be Tex with a smile and a wink, and assures me the ribs are great. That may be, but I get an eggplant sub sandwich, which is decent, but not something I would want to eat every day.


Second Church, Codman Square, Dorchester

The Second Church of Dorchester is the outstanding building in Codman Square, named in honor of the first minister of this church, Dr. John Codman.  The second parish was formed in Dorchester by 1808 and this building was built for the congregation in 1806. Obviously they must have been pretty sure they were going to be able to form a congregation. As you can see from the photograph, it is a classic white steeple New England Church that would not be out of place on the town common of any small New England town, as indeed Dorchester itself was in the early eighteenth century. As late as 1860 the entire population of Dorchester was still under 10,000 inhabitants. Today, despite constant encroachment upon its borders, Dorchester has a population close to 100,000 residents.

Old photograph of the Dorchester Temple Baptist Church. Taken from the website of the Global Ministries Christian Church, the current occupants of this 1889 Shingle Style Church designed by Arthur Vinal, whose other buildings include the very interesting Fire Station on Boylston Street in the Back Bay.  Below: The building looks almost the same today, with only a few modifications.

The church seem to be the one edifice that manages for the most part to survive the onslaught of modernization. I have passed many lovely church buildings along the road today, although most have surely changed hands and are now of a different denomination from that of  the original builders. An elegant building on the left hand side of Washington just before Welles Avenue is called the Global Ministries Christian Church, Minister Bruce Wall presiding. On a 1933 map of the area the building is called the Dorchester Temple Baptist Church. A little research indicates that the church was an offshoot of the Tremont Temple Baptist Church on Tremont Street near City Hall, and that the building was erected in 1889.  I can see that churches will probably be an important component of many of these walks, as they are survivors which have often changed with the times.IMG_8231


Six Miles to Boston. Interesting stone differing from the others in the series. the word Hemms the initials WC and 6 M to B and the initials TI surrounded by a heart. Removed to the Blake House in Everett Square sometime after 1909, this stone once stood at the corner of Mora and Washington Street in Dorchester.

The area beyond Codman Square is residential, mainly comprised of triple-deckers, the iconic residential structure of so many neighborhoods of Boston. At Mora Street was located Milestone Six, although since the time of Dr. Green it has been relocated to the front of the Blake House in Everett Square. This milestone is quite distinct from the others I have encountered as can be seen from the photograph. More research will be required to interpret the extravagant hieroglyphics, although it seems clear 6 M to B means 6 miles to Boston.

Modest two family houses along Washington as I reach Gallivan Boulevard as the road has begins to descend sharply. I look ahead and can make out the red brick buildings of Lower Mills just ahead. I pass a park, a quiet residential neighborhood, the road curves, and I begin to pass commercial buildings, insurance companies, Dolan Funeral Home, a big Star Market, and a pizza and sub place called Spukie’s ‘n Pizza. I did not know anybody still called a sub a spukie, an old North End term, but here is the proof.  In a few seconds I reach the confluence of  three routes from Boston to Lower Mills: Washington Street (the Upper Road), Adams Street (the Lower Road), and Dorchester Avenue, a turnpike built to shorten the distance from Boston even further and a walk for another day. Time for an ice cream at the Ice Creamsmith.


  1. Drake, The Town of Roxbury, 199-200.
  2. Green, Old Mile-Stones Leading From Boston , Proceedings of the Massachusetts Historical Society, Vol XLII, 99.

4 Responses to Taking the High Road in Roxbury and Dorchester

  1. Heya Gary,
    Have you or are you taking any charcoal/pencil rubbings of those stones?

    • Hi Cheryl–I have not. I have lots of photos but the stones are quite large and would need big sheets of paper. Plus I have no artistic skills and would screw it up somehow.

  2. Enjoyed your essay. Re Roxbury/ Dorchester line, I consider that Roxbury ends where Warren St meets Blue Hill Avenue. Also, Grove Hall’s zip code is 02121, which is a Dorchester zip code. I love to learn about Boston’s history and am particularly interested in the architecture of the late 19th and early 20th century. Please let me know when you’ll share your next essay.

  3. […] out of town (the Upper Boston Post Road to Watertown, the Lower Boston Post Road to Dedham, or the Upper or Lower Braintree Roads to Braintree and eventually to Plymouth). Any of these walks is […]


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