Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Milestones (WTPR#6)


The author next to the stone that started this entire project

‘Feria secunda, July 14, 1707. Mr. Antram and I, having Benjamin and David to wait on us, measured with his wheel from the Town-House Two Miles, and drove down stakes at each mile’s end, in order to place Stone-posts in convenient time. From the Town house to the Oak and Walnut, is a mile wanting 21 1/2 rods. Got home about 8 o’clock.’

Samuel Sewall Diary


3 Miles to Boston, 1729. Milestone placed by Paul Dudley

Another of the entries from the Walking the Post Road Project with relevance to this project. In this entry I describe the history of the milestones which can be found alongside the old roads in Boston. This entry corresponds to Entry #6 in the Post Road project.  Originally published Tuesday May 11, 2010.

The Parting Stone in Eliot Square, Roxbury is one in a series of stones that first attracted my attention and helped to generate my interest in the Post Road and this project. In addition to this stone (see previous entry for photos) there is a stone only a few hundred yards away on Centre Street as one walks down the hill into the Stony Brook Valley. This stone (pictured right) is harder to read, but a close inspection(click on the image and it will enlarge) reveals that it states: Boston, 3 miles, 1729. This stone represents the distance I have traveled thus far from the Old State House, although it neither informs us of the person who had it made nor tells us precisely where in Boston the traveler will find mile zero. A mile further down Centre Street in Jamaica Plain is another stone which has the inscription: B:4  1735 PD. Now we at least have a clue to this stone. Who is PD? A walk one mile further reveals all. Standing in Monument Square in Jamaica Plain is the milestone measuring 5 miles to Boston.

1007091857Proof that the milestones measure the distance to the Old State House (or the Town House as it was known in eighteenth-century Boston) could not be easier to find. One need only glance at the milestone in Jamaica Plain on which is carved the statement:

5 Miles 

Boston Townhouse 

P Dudley Esq 


        We have encountered the Dudley name in the previous entry as we passed through Dudley Square. The Dudley family has played a particularly important role in the history of Roxbury, Massachusetts, and indeed the United States. Thomas Dudley (1576-1653) was one of the five officers who travelled to America on the Arbella, arriving with Winthrop and 700 other Puritans to settle what became the Massachusetts Bay Colony. Thomas Dudley served on multiple occasions as Governor of the Colony and built the first house in Newtowne, now Cambridge. He was also instrumental in the establishment of Harvard University.  His daughter Anne (Bradstreet) is famous as the first notable poet in New England and the first woman in New England to have her works published. His son Joseph Dudley (1647-1720, thus the senior Dudley was 71 years old at the time of Joseph’s birth!) served as Governor of Massachusetts from 1702-1715, as well as in many other official positions in both New England, New York, and England.



Talk about a legacy! imagine if your name was still just where you left it almost 300 years ago!

        It is the son of Joseph Dudley, Paul Dudley (1675-1751), who interests me the most as the benefactor of the milestones in and around Boston. He was born in Roxbury a few yards away from the Parting Stone, on Meeting House Hill (Eliot Square area) where the Dudley estate encompassed 6 acres of land adjacent to the Meeting House. At the age of 10 he was admitted to Harvard (he had connections), took his first degree at the age of 15, and became a Fellow of Harvard in 1697 at the age of 21. Dudley then moved to London in the same year, studying law at the Inner Temple. In 1702, as mentioned above, his father was appointed Royal Governor of Massachusetts, while Paul Dudley became Attorney General for Massachusetts at the ripe young age of 27 (I told you, he had connections). In addition to this lofty position Dudley was also appointed as a Justice of the Peace and Registrar of Wills and Administration of Suffolk (the county in which Boston sits). Clifford Shipton, in his biography of Dudley in Sibley’s Harvard Graduates,  remarks drily that “apparently (Dudley) was the only trained lawyer in the province.” (1) He was considered high-handed by many, including Judge Samuel Sewall, whom Dudley would follow in more ways than one. In one exchange Dudley is reported to have been on his way to Boston when “He stopped and demanded of a laboring man who was passing, that he should go to his (the judge’s) house and fetch a law book he had left behind. The man seemed astonished at the demand, but asked, “Can one fetch it, sir?” “Oh, yes,” said Dudley. “Then go yourself,” was the reply.” (2)

Sewall eventually was won over by Dudley’s charms to the extent that as Chief Justice of the Superior Court of Massachusetts he supported the appointment of Dudley to the Superior Court, and in 1718 Dudley became a judge. In 1745 he became Chief Justice of the Superior Court, a position which he retained until his death in 1751. Nathaniel Shurtleff wrote of Dudley: “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…”(3)


        Wealthy members of the community in colonial Massachusetts often donated gifts of money or public amenities for the public good. A bridge called Dudley’s Bridge was built in 1720 across a brook that once traversed Dudley Square. Dudley gave a substantial sum of money to Harvard and to the Roxbury Meeting House. But it is the milestones that have been the most “durable monuments of his beneficence.”(4)  Befitting his reputation as a man who maintained a great interest in personal glorification, Dudley had the creator of the milestones carve first the date of the setting of the stone (3 mile stone, for example), then initials in the stones (4 mile stone), then progressed to “P Dudley” on the Parting Stone, and ultimately the grandiose (and very large font) “P Dudley, Esq” was added to the 5 mile stone.

Dudley was not the first person to lay milestones. Judge Sewall himself laid the first and second milestones in Boston in 1707 (see the quote at the beginning of this entry). I doubt very much that Dudley, unlike Sewall, was involved in the labor of actually measuring and laying the stones that bear his initials, based upon his reputation. The stones placed by Sewall are no longer to be found, but the first milestone lives on in the 1722 Bonner Map just before the Gate on the north side of Orange Street. This is today located about where the Massachusetts Turnpike crosses Washington Street. Milestone number two would have been located between Northampton and Lenox Streets in the South End.

I have wondered why two Superior Court justices in particular would have an interest in placing milestones and have come to the conclusion that it aided them in their work. Justices in the eighteenth century were required to “ride the circuit,” that is they were required from time to time to travel to the more remote areas of the Province as it was impractical to have everyone travel to Boston, and the population of the areas outside Boston was small enough not to warrant separate judges for each circuit. Thus they would have been well aware of the value of milestones in guiding people on their journey, and would have been mindful of creating a durable marker instead of a more perishable wooden sign. Samuel Sewall kept a detailed diary that includes all of his travels on the circuit courts, recording such details as the state of the roads, the names and quality of the taverns he visited, and other interesting details about the areas he visited. The diaries of Samuel Sewall will prove to be of great value as I travel the same roads he traveled in the early eighteenth century.


The map below is an attempt to pinpoint the location of the milestones along the road. Some still exist and are so indicated. Many are gone but their approximate historical location has been indicated. I will be updating this as I refine the information and figure out how to bring  my photos into the Google map.

The milestones provide me with the first guideposts to the original route of the road. They are found on both the road to Dedham and the road to Cambridge. On the road to Cambridge one finds milestones for Mile 4, Mile 5, Mile 6, Mile 7, and Mile 8. On the road to Dedham are the aforementioned Mile 3, 4, and 5 stones, as well as a milestone for mile 6 on the left hand side of Centre Street exactly opposite Allandale Road embedded in the wall of the Arnold Arboretum.

Milestone 6 on the road to Dedham (the Old, or Lower, Post Road).

Milestone 6 on the road to Dedham (the Old, or Lower, Post Road).

All but the 8 mile stone is a gift of Paul Dudley. After these the trail goes cold except for an occasional stone (Mile 20 in Walpole, for instance). Other milestones are found on the way to Plymouth from Roxbury in Dorchester, Milton, and Quincy, and on the “Upper Post Road” that passed through Cambridge and traveled west before heading south through Connecticut. In a future post I will return to these other milestones and describe them more fully. Perhaps other milestones exist, and I do not yet know of their existence. Perhaps I will unearth milestones thought lost (wishful thinking, but believe me, I look at every large stone I see by the side of the road). Whether I find new stones or not, the stones have already opened a door to me, and I gladly pass through it as I try to rediscover and reclaim the history of the road and the people who have passed over it for 300 and more years.


1 Clifford K. Shipton, Sibley’s Harvard Graduates, Volume IV, 1690-1700 (Cambridge: Harvard University Press, 1933), 44.

2 Francis Drake, The Town of Roxbury (Boston: Municipal Printing reprint 1905 of 1878 original), 252.

3 Nathaniel Shurtleff, quoted in “Old Milestones Leading from Boston,” a paper by Dr. Green in Proceedings of the Massachusetts Historical Society, Vol XLII, January 1909, 87.

4 Drake, 252.

One Response to Milestones (WTPR#6)

  1. The section on Samuel Sewall is especially revealing of the time and place about which you are writing. He was such a representative Puritan. He wrote about everything that he did and thought. I wish his milestones were still to be found.


Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes:
<a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>