Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Deviating from the Straight Path (WTPR#5)

The Parting Stone, Roxbury. Left leads to Dedham & Providence, right leads to Cambridge

The Parting Stone, Roxbury. Left leads to Dedham & Providence, right leads to Cambridge


“One if by land, and two if by sea; And I on the opposite shore will be”

Paul Revere’s Ride

Henry Wadsworth Longfellow


“Parting is such sweet sorrow”

Romeo and Juliet, Act 2, Scene 2

William Shakespeare

This entry is another (#5 in the original project) from the Walking the Post Road project. I have transferred it here as with the previous two because they are part of the network of old roads into and out of Boston. In particular this entry and the two proceeding it retrace the original road out of Boston. These entries take us a little more than two miles away from the “centre” of colonial  Boston, The Old State House. At Dudley Square in Roxbury the road splits for the first time. The following map shows the different routes one could take out of Boston once one reached Dudley Square. The original Project continued along the road to Dedham, and I will add the entries corresponding to that portion of the Post Road at a later date. Originally published  Wednesday, May 12, 2010.

Pity poor William Dawes. As one of the two midnight riders sent out from Boston on the night of April 18, 1775 to sound the alarm about the impending arrival of troops stationed in Boston, he deserves at least a place at the same table at which Paul Revere sits. The blame rests with Henry Wadsworth Longfellow, whose famous poem is the quintessence of artistic license (1). Revere hogs all the credit even though Dawes left earlier via the road to the Neck, “no small feat” according to David Hackett Fischer in Paul Revere’s Ride, slipped past the soldiers guarding the Gate and the fortifications, passed through Dudley Square in Roxbury, turned right and climbed the hill to the Parting Stone, where he took the right hand road and continued on through Brookline to Cambridge, and, eventually, Lexington meeting Revere who had come across to Charlestown by boat and ridden the shorter, more famous ‘Midnight Ride’ to Lexington (2). Both men accomplished their mission to alert Hancock and Adams of the impending arrival of “The Regulars,” but history and poetry have been kinder to Revere.

Dawes did get a small amount of justice  in 1896 when Helen Moore published a parody of Longfellow’s poem in the Century Magazine entitled “The Midnight Ride of William Dawes” (3):

I am a wandering, bitter shade,

Never of me was a hero made;
Poets have never sung my praise,
Nobody crowned my brow with bays;
And if you ask me the fatal cause,
I answer only, “My name was Dawes”

‘Tis all very well for the children to hear
Of the midnight ride of Paul Revere;
But why should my name be quite forgot,
Who rode as boldly and well, God wot?
Why should I ask? The reason is clear —
My name was Dawes and his Revere.

When the lights from the old North Church
flashed out,
Paul Revere was waiting about,
But I was already on my way.
The shadows of night fell cold and gray
As I rode, with never a break or a pause;
But what was the use,

when my name was Dawes!

History rings with his silvery name;
Closed to me are the portals of fame.
Had he been Dawes and I Revere,
No one had heard of him, I fear.
No one has heard of me because
He was Revere and I was Dawes.


Dawes Plaque on James Timilty Middle School Wall, 205 Roxbury Street.

So too has the route to Cambridge traveled by Dawes, and every traveler who averred the nautical option, been long forgotten. As mentioned in a previous post, the privileged position of the road on the Neck as the sole means of entry by land to Boston had been lost in the early nineteenth century. The straighter, wider, more modern Boylston, Tremont, and other streets of the Back Bay and the South End reduced Washington Street to just another road into the city. The construction of the Washington Street Elevated Railway in 1901, which ran above Washington Street from Dover Street (present East Berkeley Street, the site of the Gate) to Dudley Square in Roxbury, and from there to Forest Hills in Jamaica Plain, created a dark atmosphere down at street level and certainly stunted the development of Washington Street into a fashionable residential area until its removal in 1987. Ironically, the stations on what came to be known as the Orange line (in reference to the original name of the street, as mentioned in the previous entry, Orange Street) were designed by Alexander Wadsworth Longfellow, the nephew of the poet who slighted Dawes. Apparently this family did not like Washington Street.

Page Map 1777 smaller version

Map by Lieutenant Page showing Boston Harbor in 1775. Boston can be seen as almost an island in the harbor at center left. The Neck extends south from the town and the fortifications along the road to Roxbury can be seen (click for a larger version). Cambridge is at the very left edge of the map. Revere would have crossed to Charlestown just north of Boston, while Dawes took the “long way” around the Back Bay and the Fens, through what is today Brookline and Cambridge. Here is a link to a much more detailed version


The distance down Washington Street along the Neck from Boston Gate to the Roxbury Gate and the fortifications just beyond was approximately one mile. At this point the Neck was closer to half a mile in width. Dawes would have passed the George Tavern just as he approached the fortifications. The existence of the George was recorded as early as 1721 but it was burned by the Redcoats during the Siege of Boston shortly after Dawes passed it (4). The George was located a little to the North of the Roxbury line, at about present Lennox Street and Washington Street.


Boundary Marker between the Towns of Roxbury and Boston. Washington Street south of Thorndike Street.

A stone engraved with the date 1823 was placed on the sidewalk on the south side of Washington Street between Thorndike Street and what is today Melnea Cass Boulevard to mark the boundary between the town of Roxbury and the newly developed neighborhood of the South End of Boston. Although the stone remained after Roxbury was incorporated into the city of Boston in 1868 (and remains in the same spot), today the border of Roxbury and the South End is a subject of sometimes heated discussion. The historical border of Boston and Roxbury was located a little south of Lenox Street. The areas of mudflats off the Neck were referred to as Roxbury Flats in a 1728 map of Boston, but as the areas were reclaimed as the South End and the Back Bay they became part of Boston. Yet many people consider the South End to stop at about Massachusetts Avenue. This is very generous to Roxbury so how did this turn of events come about? The South End has become a fashionable neighborhood, while Roxbury has an unfortunate image as dangerous. Perhaps this is why real estate maps show the South End extending all the way to Melnea Cass Boulevard, which is located in what has historically been known as lower Roxbury (5).  Various houses for sale by different realtors all refer to the area as the South End, or sometimes euphemistically as “Washington Gateway,” almost certainly to avoid identifying the house as being in Roxbury.  However the Boston Globe/Boston Police Department homicide map shows various murders in the area, for example that of Alex Burgos in July 2008 or Thomas Speed in 2009, as occurring in Roxbury, when the area is historically the South End.(6)

In 1986 several residents of Roxbury, including now State Representative Byron Rushing and City Councillor Chuck Turner, proposed Massachusetts Avenue as the border for a new town to be called Mandela that would be created from neighborhoods seceding from Boston, including Roxbury, parts of Dorchester, Jamaica Plain, and Mattapan (7). The referendum was rejected but the word Mandela was painted on the side of a building visible just off Massachusetts Avenue for years after the issue had passed and the building today is known as Mandela Homes (8).


South End or Roxbury? Jim Rice Field, named for my favorite Red Sox player.

Hale Map 1814 Roxbury Line segment

Hale Map of 1814 showing Roxbury Line. All the area under discussion is clearly in Boston.

I discovered an interesting conversation on a website that took place over a murder on Lenox Street in 2005 (9). The argument revolved around an article in the Boston Herald which stated that the homicide happened in the South End to “sell papers by scaring people,” in the words of one blogger. The Boston Globe, on the other hand stated the same murder occurred in Roxbury. An argument ensued about whether it is in fact Roxbury, the kernel of the debate revolving around the unquestioned notion that the South End is ‘safe’ and Roxbury is ‘not safe’.

Perhaps a perusal of census data for the areas in question might help to clarify the discussion. The neighborhood bordering the north side of Washington Street from Massachusetts Avenue to Melnea Cass Boulevard is Ward 9, Precinct 3 which, according to the BRA compilation of 2000 census data has the following breakdown: White, non-Hispanic, 19.3%; Black, non-Hispanic, 47.4 %; Hispanic, 27.0%; Asian, 2.4%. Thus only one in five residents is White, compared to 53.2% of the population of Ward 9, Precinct 2, which is the adjoining Precinct on the other side of Massachusetts Avenue. Massachusetts Avenue, quite simply, has been a racial and class-based  dividing line, not an official border. Nat Hentoff, the jazz critic, in his autobiography Boston Boy concurs: “Not far from Northeastern’s then extremely modest campus…was another institution of learning, the Savoy Cafe. The Savoy was at the beginning of black Boston. Except for cops, the whites who crossed over the line and into the Savoy were the jazz crazed, of almost all ages, from Boston and its environs.” (10) The Savoy was located at 421 Massachusetts Avenue.

In order for a neighborhood to gentrify, stereotypes must be dispelled, hence the real estate nomenclature ‘South End’ instead of Roxbury. Ironically, in their zeal to claim the area between Massachusetts Avenue and Melnea Cass Boulevard as the fashionable South End, the real estate agents are probably closer to the truth than the police blotter. The argument continues today as evidenced by an article in the Boston Globe from December 26, 2009 (11).

I decided to take an informal survey. I found ten individuals along Washington Street between Northampton Street and Melnea Cass Boulevard who said they lived in the area in question. I then asked them what neighborhood we were standing in. All responded that it was the South End without hesitation. Where was the border with Roxbury I wondered? Nearly all the individuals suggested Melnea Cass Boulevard as the border between Roxbury and the South End. One older gentlemen said that “real old-timers will tell you that the boundary was Mass. Ave.” When I asked him why he considered it to be the South End he suggested that many people had moved across Massachusetts Avenue a few blocks and did not consider themselves to have left the neighborhood. He also told me that the many music clubs in the neighborhood like “The Baby Grand” and “Estelles” were considered to be in the South End. He finished by saying “things change.”


Eliot Burying Ground, Dudley Square.


Once I cross Melnea Cass Boulevard there is no disputing the fact that I am in Roxbury.  Dawes would have passed through the area now called Dudley Square which

was the center of colonial Roxbury, the first place upon leaving Boston where the road diverged in different directions. I pass one of the few “remains” of that era, the Eliot Burying Ground, dating from 1630. Inside are the graves of the minister John Eliot (more at a later date) and members of the Dudley family, including Governor Thomas Dudley [1653], Governor Joseph Dudley [1720], Chief Justice Paul Dudley [1752] and Colonel William Dudley [1743]. The Dudley tomb is covered with an oval marble slab which took the place of the original plate of pewter that was cut out by American soldiers at the Roxbury camp during the siege of Boston and made into bullets (12). Today’s Dudley Square is named after this illustrious Roxbury family, about whom I will have much to say in upcoming entries.

Although Dudley Square today is not the most fashionable area, efforts have been made to improve it. Roxbury developed into the center of black Boston in the twentieth century, and Dudley Square was the epicenter of African-American culture in Boston. However, judging by the beautiful but empty and boarded up buildings alone, it is obvious that the area has seen better days. Dudley Square was the subject of recent mayoral candidate and former city councilor Sam Yoon’s Master’s thesis in Public Policy at Harvard and he wrote:


Mural in Dudley Square

Dudley Square has a unique and valuable history. As a part of Roxbury, it has maintained a separate and distinct identity since the founding of the colonies as a manufacturing, commercial and retail district. As an urban marketplace, it has changed dramatically, especially during this century, as did many of the urban centers in America. The flood of immigrants to cities during the early 20th century, the migration of African-Americans from the South, the rise and decline of the manufacturing sector, and suburbanization or “white flight” have all changed the character and usage of Dudley Square over the years.

However, buildings change more slowly than businesses and residents, and the large, vacant lots, buildings and upper-floor space in Dudley Square testify to the magnitude of the changes that have taken place there in recent decades. And yet despite the gloom that these stately, vacant structures impose upon Dudley Square, retail businesses continue to survive and even thrive there.” (13)


Dudley Square Bus Station

I stop for lunch at one of the thriving restaurants in Dudley Square, Haley House Bakery Cafe which was started by an organization that works to alleviate the problems caused by homelessness. It is an oasis of calm in a busy and sometimes unpleasant area. The only time I have ever been harassed by anybody about being in the wrong neighborhood was on Washington Street near the cafe, although the gentleman who addressed his colorful epithets at me was in the process of using a coat hanger to bust into someone’s car and seemed to be somewhat unsteady, so I did not take it personally. Some things never change. Here is an example from 1820: “It was at this very time that two young men, to close a drunken nocturnal frolic, broke into Rev. Dr. Porter’s church, tore the cushions in pieces, destroyed the Bible, removed the hearse from the graveyard, and performed other acts equally disgraceful.” (14)

Haley House is located near the site of the Greyhound tavern, opposite Vernon Street, “which for more than a century was the principal public house in Roxbury on the only road leading into Boston.”(15)  Samuel Sewall paid a visit on July 11, 1687, but it had ceased to be a tavern by 1776.  In 1741 there is a record of an exhibit at the Greyhound Tavern of a live “catamount” (puma, mountain lion, cougar, panther) that had been captured about 80 miles west (16). A tavern referred to as ‘Shippery’s’ –after the landlord of the time John Shippey (sic), (born 1695)– is recorded in Thomas Prince’s Almanac of 1731 as being located two miles from the town house, in Roxbury (17).  The Prince Almanac will prove very useful as I journey forth into the countryside trying to determine the correct route of the original road.



Right side of the three-sided Parting Stone . Dawes went right, I went left.


Left side of the Parting Stone. The Post Road to Dedham, Providence, and New York.

I turn right and leave Washington Street after two and a half miles. Washington Street continues past Dudley Square for miles to the Rhode Island border, and I will revisit this road, which was constructed as a turnpike in the early 1800s, time and again as I make my way to Rhode Island. The original road veers right and is called Roxbury Street. Roxbury Street leads out of Dudley Square and starts up the first hill I have encountered, an indication we are leaving the marshes of Boston behind for the rocky countryside. After a few minutes I reach a beautiful neighborhood with a stately wooden church and some eighteenth-century houses and shortly arrive at a stone marker on the corner of Roxbury and Centre Streets. The Parting Stone marks the divergence of the Post Road for the first time. The road to the right, as indicated on the stone, goes to Cambridge and Watertown. This is the route Dawes took to get to Lexington, passing through Brookline on what is today Harvard Street. The road to the left is the road for Dedham and Rhode Island. This is the road I take to continue on my journey. I will return to the Cambridge road and its role as an important Post Road at a later date. Now I must take my leave of William Dawes, as we part and go our separate ways. Whether with a lemonade in Haley House Cafe or a flip in the now vanished Greyhound Tavern or the George Tavern I raise my glass to William Dawes as he joins Paul Revere at his rightful place at the table of Heroes of the Revolution.


1  Accessed May 5, 2010.

2 David Hackett Fischer, Paul Revere’s Ride (New York: Oxford University Press, 1994), 97. Of great interest in this book are the historiographical essays, particularly “The Union in Crisis: Longfellow’s Myth of the Lone Rider”, 331-333. Note: The descendants of the William Dawes are justifiably annoyed at this historical slight as this website demonstrates. Accessed May 5, 2010.

4 Francis Drake, The Town of Roxbury (Boston: Municipal Printing reprint 1905 of 1878 original), 84.

5  A map of the neighborhood by a real estate oriented web site. I used the address of the site of Alex Burgos’ homicide (see below) as the point of reference for my search. Accessed May 5, 2010.

6  Information about murder of Alex Burgos in “Roxbury.” Note that other homicides in other years in the same area are referred to as taking place in Roxbury. The Boston Police district which covers this area is D-4 which is listed as Back Bay/South End/Fenway, just to confuse matters more. The D-4 boundary is Melnea Cass Boulevard, and the area on the other side, B-2, is referred to as Roxbury. Accessed May 5, 2010.

7  An article about the Mandela proposal on WGBH Ten O’clock news from 1986. Accessed May 5, 2010.

8 . This article describes how the housing complex changed its name in 1987 in support of the proposed Mandela secession movement.


10 Nat Hentoff, Boston Boy, (Boston: Faber & Faber, 1986), 110. Hentoff also revisits the Boston Jazz scene of the 1940s and 1950s here:



13 Sam Yoon, “The Dudley Square Retail District”, The Rappaport Institute for Greater Boston, John F. Kennedy School of Government, Harvard University, April 12, 1995.

14 A Volume of Records Relating to the Early History of Boston, Boston Municipal Registry Department, 1909, 295.

15 Justin Winsor, Memorial History of Boston (Boston: Osgood, 1880), 421.

16 Francis Drake, The Town of Roxbury (Boston: Municipal Printing, 1905 reprint of 1878 original), 164.

17 Thomas Prince, “Vade Mecum for America”, or a companion for traders and travelers (Boston:Kneeland and Green for D Henchman & T Hancock, 1731),199. In Evans Boston Public Library.

One Response to Deviating from the Straight Path (WTPR#5)

  1. […] in 1778 and ended up in the hands of William Cogswell who, with his brother-in-law William Dawes of Midnight Ride fame, moved here from Boston and took over Barnes’ potash manufacturing operation. Dawes lived […]


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