Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Exit Timing


The Red Fort, Delhi, India. In March, 2016 it took me 24 hours to reach this sight from my doorstep in Boston. In the 18th century it took 24 hours to travel the 40 miles to Providence, Rhode Island or to Worcester, Massachusetts. Photograph of the author.

A brief analysis of the routes out of Boston to Watertown and beyond, also called the Upper Post Road.

It is easy to take the relative ease of travel in the modern world for granted. I recently visited India for the first time and, in the course of traveling, I reflected how long and difficult a journey of this magnitude would have been as recently as a century ago.  To be honest, I have been reflecting on this topic since childhood as I have always been fascinated by maps, travelers, and explorers. I apparently am not the only person who thinks about travel in the past, as the recent revival of an early twentieth century isochronic map (shown below) indicates.

This beautiful map, plate 12B of the geographer John G. Bartholomew’s 1914  Atlas of Economic Geography, has recently been making the rounds of the internet, first (re)appearing by my reckoning in the Economist’s sister publication Intelligent Life (recently renamed 1843). Bartholomew’s map shows the approximate time it would take the traveler to reach any destination in the world from London.  To reach India for example, involved a journey of anywhere from ten to twenty days (a reminder: click on the images for a large and more detailed version of the various maps, charts, and photographs on these pages). This was a dramatic improvement over the 1498 voyage of Vasco da Gama, the first European to reach India by sea, who left Lisbon on July 8, 1497 and arrived in Calicut (today’s Kozhikode) on the Malabar Coast ten months later on May 20, 1498. The fact that there is a ten day window in Bartholomew’s map is testimony to the fact that travel even a century ago was still quite unpredictable and difficult.

1914 Isochronic Map of Travel time from London, Plate 12B- John G Bartholomew

A map from John G. Bartholomew’s Atlas of Economic Geography showing the travel times from London to any point in the world in the early twentieth century. public source.

By contrast, I left my house on a Thursday morning in March at 8 a.m. heading for Logan airport on the MBTA (the subway or metro or, as it is known in Boston, the ‘T’ ) to catch an 11:55 a.m. flight to Dubai on Emirates Air, followed by a transfer to a second flight on Emirates to Delhi. The flight from Boston to Dubai was 12 hours and 15 minutes in length, which today seems an eternity to be in transit. After a layover of 1 hour and 40 minutes in the giant international shopping mall/airport on the edge of both the Arabian Desert and the Persian Gulf, I caught the second flight, which crossed the Arabian Sea in 3 hours and 25 minutes, and arrived on time in Delhi at 2:45 p.m. on Friday. Taking the 9 hour 30 minute time difference into account, the total trip time from gate to gate was 17 hour 20 minutes. After passing through customs and immigration, I took a taxi from the airport to our guest house in New Delhi arriving at 5:00 p.m. through more than a bit of traffic (it is Delhi after all!). Factoring in the time involved in getting to and from the airport, the door to door travel time from my house in Boston to the Lutyen’s Bungalow Guest House in New Delhi was just about 24 hours, give or take an hour. Thus my trip was at least ten times faster than the fastest voyage from London to Delhi only a century ago.


It is with this frame of reference in mind that I undertook to walk along the old route that connected Boston to the west. Not only was travel time much greater in the eighteenth century, but the route the traveler from Boston to the hinterlands was required to take was also much more circuitous.  As I have stated in these entries on more than one occasion, Boston was almost entirely surrounded by water in the colonial era and only one road allowed for travel by land out of Boston, along today’s Washington Street from the Old State House to Dudley Square in Roxbury. After reaching Roxbury the traveler had three choices, all of which I have described previously: the upper or lower roads to Braintree and Plymouth, or the road to Cambridge and Dedham. After passing the church in Eliot Square in Roxbury, the traveler again had a decision at the so-called ‘Parting Stone’: the road left leading to Jamaica Plain, Dedham, Providence, and New York, or the road to the right leading to Brookline and Cambridge and points west. Following the road to Cambridge, the traveler reached today’s Brookline Village, a little more than four miles distant from the starting point in Boston, where three more choices awaited. The road to the left, today’s Walnut Street, led to Newton, while the road to the right quickly bifurcated into the road to Cambridge (today’s Harvard Street/Avenue, a road I also wrote about in a previous entry) and the road to Watertown. From Watertown, the main road led west to Sudbury, Worcester, Springfield, Hartford, and New York. This road was referred to as the Western Road, or the Upper Post Road. The road to Dedham, Providence and New York mentioned above was referred to as the Lower Post Road, and was the subject of a previous project of mine, entitled Walking the Post Road.

The most direct route today from the Old State House to the bridge over the Charles River at Watertown, according to Google maps, is 6.7 miles (The straight line distance is 6.5 miles so this is about as direct a route one can take). From the Old State House the route follows Cambridge Street (see Google map purple line) to cross the Charles River over the Longfellow Bridge, then heads along Main Street in Cambridge to Massachusetts Avenue into Central Square in Cambridge. From here Western Avenue is followed back across the Charles River into Allston/Brighton, where the road continues as Western Avenue across Allston/Brighton until the river is reached again. After crossing the river for a third time the road becomes Arsenal Street which leads directly into Watertown.

It is important to note that, in 1790, not one of these roads or bridges existed. Thus, the early traveler who wished to strike out for Sudbury or Springfield or Hartford Connecticut, or indeed to head to the rest of the colonies via the interior route (as opposed to the coastal route I followed in my Walking the Post Road project), was obliged to head down the Shawmut peninsula and out along the road to Watertown, today’s Washington Street in Brookline and Brighton. It was also possible to reach Watertown by the road to Cambridge, and indeed some travelers did take this road, first reaching Harvard Square then following Brattle Street to today’s Mount Auburn Street. Samuel Sewall seems to have followed this route on most of the visits to Watertown he describes in his diary. However, it is 2.6 miles longer, making a 3 hour walk almost an hour longer.  A careful reading of Sewall’s diary entries leads me to conclude that there were specific reasons he undertook to travel the slightly longer route. He often stopped in Cambridge to visit people or to meet up with people to journey together to Watertown and points west. His farm was along the Harvard Road beyond Brookline Village, so perhaps he stopped there to check up on things when he was in the neighborhood. Also there is a possibility that the Watertown Bridge may not have been fully operational for periods in which the diary was written and so he was obliged to travel via Cambridge.

For most travelers, however, it would seem that the most direct route from Boston to points west would take them along Washington Street in Brookline to Brighton center, and on to the bridge at the Charles River at Watertown. This “direct” route measures about 9.1 miles, an extra 2.4 miles more traveling compared to today’s direct route, an extra 45 minutes walk.

Additionally, it was also possible, and likely, that some travelers would cross the river from the North End of Boston to Charlestown and follow what is now Main Street to today’s Sullivan Square, where the road now called Washington Street in Somerville and Kirkland Street in Cambridge led to Harvard Square. From here the traveler would follow Brattle Street as described above to Watertown Square, for a total distance of 8.3 miles. I will point out that, although the route is shorter than the distance traveled via Boston Neck, the ferry crossing entailed an extra element of complexity that likely lengthened the journey time.


Bridge across the Charles River at Watertown, Massachusetts. All roads leading west out of Boston converge here and merge to become the Upper Post Road. Photograph of the author.

 A remarkably clear and extremely interesting illustrated map of the Boston area in 1775 (below) compiled by J. DeCosta (I have not found out much about him, not even his first name) shows all the routes to Watertown from Boston: the direct way from Brookline Village, the indirect route through Harvard Square from Brookline Village (the ‘Sewall’ Route), and the route from Charlestown (the first part of which was also the same route as Paul Revere’s ride to Lexington). It also illustrates another possible reason that Sewall and others might have taken the route to Watertown via Cambridge: the direct route to Watertown was distinctly more hilly. Travelling over the Cambridge Bridge and turning left on to Brattle Street across what is shown on the map as Watertown Plain provided the advantage of more level ground.

1775 DeCosta Map closeup of routes from Boston

1775 Map by J. DeCosta, depicting the various military encampments in the Boston area, is one of the clearest maps depicting the main roads leading in and out of the town of Boston in 1775. Although the Upper Road to Braintree and the road to Newton are missing, all the other major roads are shown. Today’s entry concerns the road leading west out of Roxbury over “Watertown Hill” which crosses the Charles River over the Watertown Bridge. As is clear from the map this is the most direct way out of Boston by land (i.e.) not crossing the river to Charlestown or Cambridge. This map is from The Leventhal Map Collection at the Boston Public Library

Three routes from Boston to Watertown: one from Charlestown Ferry to Harvard Square through Somerville, and then west along Brattle Street, the other two via Boston Neck and Brookline Village, where they split into the direct road to the bridge at Watertown through Brookline, Brighton, and Newton on the left and the road to Watertown via Brookline, Allston, across the river to Harvard Square where it meets up with the road from Charlestown. Each merits a distinct entry as each pass through some of the richest troves of historical treasure in America: The Battle of Bunker Hill and Paul Revere’s Ride, The road to Cambridge and  Harvard, America’s earliest institution of higher learning, the road of William Dawes, General Knox, and George Washington, and much more.

As I have previously written about the road to Cambridge from Roxbury, the next two entries will deal with the particulars of each of the remaining two roads. The first of these will be the four and a half miles from Brookline Village to Watertown along the former ‘Watertown Road’.  Subsequently, I will explore the road through Charlestown and Somerville, then continue along the Brattle Street section shared by two of the routes. After I have linked up all three of the roads in Watertown, I plan to head out along the Great Western Road as far as possible to look for evidence of the oldest road and to find traces of previous travelers and to piece together the route of the Upper Post Road as I did for the Lower Post Road. I will leave the strictly defined parameters of a ‘Boston Ramble,’ but then rules are made to be broken.


The darkest blue regions of Bartholomew’s map show the areas of the world which took the longest time to reach from London in 1914: The Congo and the Sahara in Africa, the Amazon basin, the Rub’ al Khali, the Australian Outback, New Guinea, Tibet, Xinjiang, Mongolia, Siberia. When I was young I was fascinated by the intrepid explorers who ventured to these and other exotic locales and was determined to follow in their footsteps and explore the furthest reaches of the planet as well. As I grew older I realized that these exotic locales were not in fact so difficult to reach anymore and that they had in the main been combed over by generations of like-minded individuals eager to find their own lost Mayan temple or Macchu Pichu, their own Lost Ark or Shangri La.

 The irony of modern travel is that much of the ‘mysterious’ world I wanted to discover is as easy to reach today as it was to reach California a century ago. I do appreciate the fact that I can hop on a plane and be on the other side of the planet in the course of a day. But I often feel the mystery has been removed by the very ease of travel and the ability to ‘see’ any part of the world on a screen while sitting on my sofa. I might be having new experiences and seeing the world but I feel that I am in no way an intrepid explorer.

On the other hand, the old road beneath my feet, the winding road out of Boston and into the country that likely existed in some form before any Europeans settled these shores, has been traveled for centuries by the Massachusett people and by people from Massachusetts, by English farmers, by judges riding the circuit, by newlyweds and pioneers, by redcoats and by patriots, and by presidents, and yet still maintains the air of mystery I craved as a child. It is as though the Heirloom Seal of the Realm, or a lost Mayan temple, or Captain Kidd’s buried treasure has been lain at my feet waiting to be discovered. The old roads are largely forgotten and the remaining relics are left to molder as we zoom off to discover the wonders of Peru or Bali, of New Zealand or South Africa or even to spend a weekend in Miami or New York. To peel back the layers of asphalt and reconnect the ancient pathway to the modern road, to bring these old roads back to their rightful place as exotic treasures of the past that still have something to offer and that deserve to be explored, at the pace of the original travelers, is an adventure in its own right. As I have stated before and is implied in the very title of this project, the best way to appreciate the road is to walk, which is frequently how the eighteenth century traveler might have made his way to Watertown from Boston.

The formula for calculating the rate of travel is r=d/t where r is the rate in unit distance per unit time, d is the distance traveled, and t is the time required to complete the unit distance. In the modern world r has been increased by decreasing the amount of time required to complete the required distance. The increased rate of travel in the modern world, in my view, is inversely proportional to the sense of adventure experienced on a journey. Thus, to restore a sense of adventure and to be able to explore and appreciate the experience of travel more fully, the time required to complete a trip needs to increase. Idling at an airport is not the solution to restoring the balance of time and distance required for an ‘adventure.’  Walking, observing my surroundings, and researching the roads traveled is an excellent way to restore the balance and to recover the sense of discovery I have always sought when I travel.

A series of Isochronic Map of the United States. Each map shows the time it would take to travel to any point in the country from New York over the course of two centuries.

A series of Isochronic Map of the United States from The Atlas of Historical Geography. Each map shows the time it would take to travel to any point in the country from New York over the course of two centuries. For example, in 1800 the time required to reach Boston from New York was four days. Today, this trip can be done in four hours.

The walk from the Old State House in Boston to Watertown Square via any of the old routes takes only slightly less time than it took me to fly across the Arabian Sea! So it is fitting to end with a series of isochronic maps, from the Atlas of Historical Geography of the United States, which show the time it took to reach various places in the United States from New York City at different points in history. The first map, of rates of travel in 1800, shows that Boston was a four day journey from New York, four times longer than it took me to reach Delhi from Boston.  Even as recently as 1930, it was barely possible to reach Denver or San Antonio from New York in 24 hours. The next time I am grumpy about a flight delay, I will consider poor Samuel Sewall riding the circuit in Massachusetts on horseback, and go back to playing with my iPhone. Louis C.K. is right…..

3 Responses to Exit Timing

  1. […] The distance from what is now the Old State House in Boston to Watertown bridge along the original eighteenth-century route is almost exactly nine miles, while a seven-mile walk from Watertown bridge along the original […]

  2. […] which was a slightly shorter route west from Boston in the eighteenth century.13See my entry Exit Timing for a discussion of different routes west out of Boston over […]

  3. […] bridge shortened the distance to Boston from the west by two miles, as I have discussed in previous entries (and this one). I am in the process of creating a map that color codes every mile from Boston along […]


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