Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Milestone 5, Jamaica Plain, Massachusetts: The Art of Walking (WTPR #1)

“I have met but one or two persons in the course of my life who understood the art of walking…”

Henry David Thoreau, Walking


This is the very first of the entries from my previous project, Walking the Post Road, which I have been slowly transferring over to this project for a number of 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 Wednesday, March 1, 2010, as entry #1, Mile 5.


I have decided to walk from Boston to New York.

I could, of course, choose a more exotic setting for a long-distance perambulation such as the Camino de Santiago (of which more later) in Spain and France or the Via Appia in Italy or the Silk Road or the Karakoram Highway in Asia or the overland route from Cairo to Capetown or, closer to home, the Appalachian Trail, or I simply could walk across America. Instead I choose to walk out my front door, turn left at the crossroads and keep going for 230 or so miles until I get to the Bowling Green in Lower Manhattan.

        The non-walker might suggest more rapid forms of transportation in the interest of time. I could drive, fly, take a bus, or take the train (though it is debatable at times whether any of these modes of transportation are, indeed, faster).  What is the point of wandering through busy towns and past suburban shopping malls? What is the point of walking on an old road when you could take the highway? Isn’t this just a waste of time and energy?

        The reasons for deciding to make this trip are manifold. First, I am cheap. I figured my feet were a less expensive way to go. Second, I like walking. I also enjoy bumping into things I had not anticipated. I like the voyage itself sometimes as much as or more than the destination. I also enjoy collecting information and processing it, and walking gives me more time to both collect and process many facts about small towns, about the landscape of New England, about the historical significance of the road and of the houses, the fields, and the towns it passes. I am a birdwatcher and it is quite difficult to watch birds at 65 miles per hour, but quite enjoyable at a walking pace.

        Here is where I pull out the big gun, namely, one Henry David Thoreau, who wrote an essay entitled Walking, in which he describes the pleasures, purposes, and advantages of walking.  He also believes that people do not walk properly: “I have met but one or two persons in the course of my life who understood the art of walking.”1 Henry David Thoreau, Walking in The Portable Thoreau, 3rd edition, ed. Carl Bode (New York: Viking Press, 1970) 592. Thoreau did most of his travels on foot or in a canoe, observing small details as he went, building from the seemingly trivial the arguments and essays for which he is justifiably world-renowned.  I want to be one of those one or two to whom he might be referring.  Life on Earth might be a good sight more enjoyable if everyone read a little Thoreau instead of sticking Thoreau quotations on the bumpers of their Toyota SUVs.

     There is an underlying goal and a concrete starting point for this madness. In the mid 1980s I watched La Voie Lactee (a movie by the Spanish director Luis Bunuel). In this film, two “pilgrims” travel to the holy site of Santiago de Compostela, a city in Galicia. This allegorical film has our heroes meet with a variety of adventures and characters. The film itself is interesting in its own right, and I will discuss it in detail later. What it did for me however, was to help generate an idea which has percolated for a quarter of a century. I became obsessed with the idea of walking from Paris to Santiago on the ancient trail, the Chemin de Saint Jacques in France and, after passing through Roncevalles in the Pyrenees, El Camino de Santiago (or Camino Frances as it is more properly known).

    Anyone who knows me realizes that it was not a religious obsession. Richard Dawkins is the type of saint I admire. Rather, I was captivated by the idea of wandering roads that had been traveled by many people over long periods of time. It also occurred to me that people once walked great distances to get someplace because they had no other choice. One might argue that Homo sapiens evolved with a capacity, born of necessity, to walk long distances.  The upshot is that I began to walk more and to maintain an obsession with Santiago.

    There are a number of problems with walking to Santiago which I could describe in detail, but the fact remains that twenty-five years went by, and, except for a day or two now and then over the years, I have not walked the Santiago trail. 


 Just up the street from the house in which I live is a stone marker tucked away in a traffic intersection bearing the inscription

5 miles

Boston Townhouse

P Dudley, Esq.


A couple of questions popped into my head the first time I saw this stone discreetly calling out to the occasional passerby who notices it. Because I live within the city limits of Boston it struck me as curious that ‘Boston’ was still five miles away. Which way to Boston? There are twenty roads leading into the Hub, so why is this stone here and not elsewhere indicating the main-traveled road to the eighteenth-century traveler. A resident of my neighborhood, even in the eighteenth-century, would surely be able to find his or her way to the city center without the aid of a milestone. So this was clearly meant for strangers; therefore this road, besides going to Boston, must come from somewhere else. Where? Who was P Dudley? Why would he put up a stone in 1735 telling the aforementioned traveler the remaining distance to Boston? Is this the only stone of its type or are there more?

    The milestone began to preoccupy my thoughts.  I would walk over to it with my dog and stare at it while people stared at me. I would touch it as though it were a holy relic.  I researched the road and the person who erected the stone. I even read some books by and about both people who had traveled past the milestone and those people who traveled past the spot where the milestone is before it existed. Finally I decided to see for myself where the road went.  I would walk the road myself.  Wherever it went I would follow. It would get me out of the house and get me focused on a project. Where does the road go? Is it still there? How does the road compare to the one traveled by my predecessors on this voyage? I would make a pilgrimage on this road, aspiring in the end to discover the meaning of the Post Road. Again, Thoreau said it best: “For every walk is a sort of crusade, preached by some Peter the Hermit in us, to go forth and reconquer this Holy Land from the hands of the infidels.”2 Thoreau, Walking, 593.

Update April 6, 2022. I completed this project in New York on February 25, 2011 and published the last entry (WTPR#65) on April 19, 2011. Individual entries are being transferred to this website from the unreliable one where they now reside and have (WTPR#X) in the title.

I walked the Camino de Santiago in 2013, starting in Roncevalles, at the frontier with France, on April 30 and finishing in Santiago, Galicia on May 31, 2013. Total distance 810 km, a little over 500 miles, not counting numerous detours and bird-watching side-trips. Since so much has been written about the walk I just enjoyed it. One of the best things I have ever done.

2 Responses to Milestone 5, Jamaica Plain, Massachusetts: The Art of Walking (WTPR #1)

  1. […] Milestone in Jamaica Plain, Massachusetts. Art and Artifact. Where it all started. See The Art of Walking […]

  2. […] years later, on March 1, 2010, that I finally published the first of the entries that would become Walking the Post Road. I spent most of those intervening ten years wandering segments of the old road, visiting local […]


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