Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Jamaica Plain: Home Stretch (WTPR#9)

Loring Greenough House, Jamaica Plain, Massachusetts. built in 1760.

“But I have promises to keep, 

And miles to go before I sleep,

 And miles to go before I sleep.”

Robert Frost from “Stopping by Woods on a Snowy Evening”

This is another of the entries from my previous project, Walking the Post Road, which I have transferred over to this project for two reasons. The first reason is that it is relevant to this project in that it is a ‘ramble’ about Boston. The second reason is that the previous project was done on Apple’s iweb, which is no longer supported by Apple and, consequently, the website is slowly decaying. I will eventually revisit that project and bring the entire site up to date. In the meantime readers are welcome to comment upon this entry as part of this project. It has been updated and edited slightly from the original version which was published on Tuesday, May 25, 2010, as entry #9, Mile 5.

One thousand paces. One mile is milia passuum, one thousand paces in Latin. The Romans are believed to be the first to use milestones, columns with the miles inscribed on them placed along the side of the road. A Roman mile is actually slightly shorter than the modern statute mile. The Roman mile was reckoned by the distance of a pace, which is made up of two steps; that is consecutive left then right footfall. A pace was considered to be five Roman feet, or pes, which in turn was made of up twelve uniciae, which measures slightly less than a modern inch. Thus a Roman foot measured about 11.6 inches and 5,000 feet made up a mile, so the Roman mile works out to approximately 4840 feet, about 440 feet short of a modern mile, the distance of which was set by an act of Parliament in 1592, during the reign of Queen Elizabeth I.¹  I have yet to discover the reason for the discrepancy, but I am pretty sure it is not because Romans had small feet.

Roman roads were designed to transport goods and soldiers as efficiently and directly as possible and were, therefore, constructed to be as straight as possible. Centre Street, the road leading from the milestone in Hyde Square to the next milestone, in Monument Square, is quite straight as well as being relatively flat; hence it is no surprise that it is the main street of Jamaica Plain. The Jamaica part of the name has been a subject of dispute, variously attributed to the Island of Jamaica (rum related), and an old Indian woman Jamaco who supposedly inhabited the area, but most likely is a corruption of the name Cutshamekin. Cutshamekin was the brother of the sachem Chickatawbut of the Massachuset Indians who inhabited the area in and around Boston when the English began to settle in 1630. Chickatawbut died in 1633 of smallpox, and Cutshamekin became regent of the Massachuset and the guardian of the son and heir of Chickatawbut, Josias Chickatawbut. It is speculated that there was a summer encampment of the Massachuset Indians near what is now Jamaica Pond. Little evidence but place names remain of the once vibrant culture of this branch of the Algonquian Indians.²


The 1st Church of Jamaica Plain, originally the 3rd Church of Roxbury, established 1769. The present building dates from 1853, replacing an earlier wooden structure. The milestone is just outside the photograph to the left of the intersection of the two crosswalks.

In an earlier post, I explained that Jamaica Plain originally made up a part of the town of Roxbury. It is in the Town Records of Roxbury that one finds a reference to the road on which I am standing. On January 4, 1663 a record was made that “The Highway from Elder Heath’s lane and so towards the Great Pond leading to Dedham [is] to be fower rodds [four rods, a rod being five and a half yards or sixteen and a half feet] throughout.”³  This is a clear reference to what became the Post Road and is the earliest reference to this road I have yet found, although as we will see in a later entry, this road may in fact be far older, predating the arrival of English settlers. Four years later the area itself is mentioned by name when Hugh Thomas conveyed property here for the benefit of a school “to the people at the Jamaica end of town.” (4) The population at the Jamaica end of town was still quite small throughout the eighteenth century as the area was made up primarily of farms and estates. Almost none of the estates survive, as most were converted into housing developments in the latter half of the nineteenth century for commuters to Boston. Three estates are worthy of mention: one was owned by a famous figure in the history of the American Revolution, the land of one is now a well known landmark, and the house of another survives in Monument Square yards from the five mile stone.
John Hancock occupied a mansion near Monument Square until he was accused of pecuniary discrepancies with regard to the funds at Harvard College, of which he was treasurer in the 1770s, by the minister of the Church, the Reverend Dr. William Morgan, himself an overseer of Harvard Colllege. Hancock was offended and quickly removed himself to Boston.
The Loring Greenough was built in 1760 and is still in Monument Square. Joshua Loring, the original owner, was a Tory and was forced to flee to England for safety. After the war his house was confiscated and sold at auction, eventually falling into the hands of Anne Doane, who married David Greenough in 1784. The Greenough family occupied the house for 140 years, finally opting to sell it in 1924. The imminent destruction of the house was averted by the organization of a group called the Tuesday Club, which saved and have since been stewards of the house to this day.(5)
One of the largest landholders in Jamaica Plain was the Weld family. William Weld, the former Governor of Massachusetts, is a direct descendant of the original landowner Joseph Weld. The Welds owned roughly 280 acres for a century and a half from 1643. In 1800 the estate was sold to Benjamin Bussey who donated it to Harvard upon his death in 1842 with the stipulation that the land be used for an institution dedicated to horticulture. A second legacy bequeathed to Harvard in a similar vein by James Arnold, combined with that of Bussey, led to the creation of the Arnold Arboretum, one of the most important botanical gardens in the world. As we shall see, the Post Road passes along the north side of the Arboretum for almost a mile.


Paul Dudley milestone, Monument Square Jamaica Plain, MA.

One thousand paces down the relatively straight and flat straight stretch of the “fower rodd” highway brings me back to the starting point, the touchstone of this endeavor, the stone placed by Paul Dudley in 1735 indicating five miles to Boston. After initiating this project in the winter I have only now managed to return to my home base. But I have begun to investigate the road and its myriad stories, and I have allowed myself to tell this story to a larger public.
The truth is that I have walked many miles of this road many times before, and this latest walk is merely the culmination and synthesis of these efforts. I originally began this investigation on June 2, 1999, six months after dropping out of graduate school, when I walked up to the milestone in Monument Square, said goodbye to my wife, and wandered down the road, with no foreknowledge whatsoever of what the road was or where it went. I followed the road for about 65 miles to Wickford, Rhode Island before returning home. I then walked portions of the road, visited sites along the way, and researched this project sporadically for the next decade. The Post Road threatened to become, like my interest in the road to Santiago, another in a series of dead-end projects I had embarked upon over the course of my life. As time passed and I had produced nothing but reams of information hidden away in my office and my brain, my enthusiasm for investigating the unknown weakened and the project was became more of a yoke around my neck than an exciting physical and intellectual endeavor. Then this February I was aroused from my state of torpor by the discovery of the imminent publication of a book on the Post Road, the first in almost fifty years and confirmation of my worst fears that my project was about to be made redundant, that I would get “scooped,” as I had been in graduate school, mainly owing to my inability to bring the project to completion.
Depressed by this turn of events I was on the verge of admitting failure when I was idly searching my Bookmarks menu one day and saw a blog by a friend of mine that he had started the previous year. I previously had paid little heed to the burgeoning blogosphere, but knowing someone who actually produced one of these blogs gave me inspiration. Suddenly I found a new purpose: I would now get the information I had stored in files, in my computer, and in my head out to a larger audience using the Internet, in the form of a blog. Not only would it be “published,” that is, made public, but the format forces me to be disciplined about producing new material in a timely fashion. The format also perfectly suits the philosophy of “sauntering” I hope to convey by forcing me to focus on a small section of the road for each entry I post.
I had always taken photographs with my cell phone camera as I made my way down various portions of the road with no idea what to do with them– again a blog would solve that problem. I also like the ability to hyperlink references to ideas I would like to discuss more fully but cannot in the interest of time, space, and continuity. In summary, I have spent these last weeks renewing my interest in this project and making an effort to present the information in an entertaining and informative manner.
Now I have returned to the spot where it all started, eleven years ago as well as in the first entry of this blog. I am ready to head back out into the unknown, to follow the road where it will take me and to bring back stories and insights as I follow the road to the end, or at least until I get to New York. I hope you have been interested thus far, and I hope you will continue to follow me as I leave the safety and comfort of the known for the mystery and excitement of the unknown road ahead.

1832 map of Jamaica Plain by J.G. Hales. The 3rd Church of Roxbury or 1st Church of Jamaica Plain as it came to be known, is left of center, indicated by the steeple. This area is now called Monument Square, where the Loring-Greenough House (the square below the church on the other side of the square above the letter A) and the Paul Dudley milestone indicating five miles to Boston are to be found. Centre Street  is the long, straight road heading to the right away from the church to Hyde Square (the intersection with Perkins Street at right); Centre Street also continues left away from the church, turning left at the intersection and heading to West Roxbury, Dedham, Providence, and eventually New York. Jamaica Pond is also visible top center, as is the Stony Brook, at bottom right

2018 Update: I continued on from Jamaica Plain and completed this project in April 2011, walking all the way to New York via Providence and New Haven along the ‘Lower Post Road’. I later walked the 500 miles of the Santiago ‘Camino’ from the Spain/France Border at Roncesvalles to the Cathedral at Santiago de Compostela, Galicia in May/June 2013. Subsequently I began this project, which has covered a variety of different walks, as can be seen by clicking on the various categories at left. I still live in Jamaica Plain and the next entry in this project will be a walk in the ‘Better Know a Precinct’ series which will cover my home precinct (ward 19, precinct 6). I am also currently walking the ‘Upper’ Post Road west from Watertown to Springfield, Hartford, and eventually meeting up with the lower road at New Haven. Updates will appear here as I write them.


  3. Robert J. Dunkle and Ann S. Lainhart ed., Town Records of Roxbury, Massachusetts 1647-1730. being volume one of the Original (Boston: NE Hist Gen Soc, 1997), 42.
  4. Francis S. Drake,The Town of Roxbury, 1908, 404.

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