America’s first “interstate” highway was built to link Boston to New York City. The 17th century Boston Post Road is often overlooked in the city’s early history, but it marked the earliest and one of the most ambitious attempts to knit the fragmented English colonies of North America into a single, cohesive entity. From Boston’s first post office, which accepted only overseas letters, to the post riders who braved “mountainous passages” and roaring rivers, this primitive road network was the original interstate, forged not just for convenience, but for the survival of the British colonial project.
In this episode, we’ll explore how the Boston Post Road evolved from an indigenous trade route into the King’s best highway, a crucial artery for colonial and early federal correspondence. We’ll trace the routes of the upper Post Road through the wilderness of Central Massachusetts and Connecticut and the coastal lower Post Road that shaped the roads and transportation networks of modern New England. Along the way, we’ll uncover the stories of the people who marked the miles, from wealthy landowners like Paul Dudley, to determined travelers like Madam Sarah Kemble Knight, to George Washington, who arrived in Boston for his first official visit as President along the Post Road.
Boston’s 17th Century Interstate System

- The Boston Globe, Mon, Dec 28, 1885
- Moll, Herman. “New England, New York, New Jersey and Pensilvania,” Atlas Minor, 1729.
- Sewall, Samuel, 1652-1730. Diary of Samuel Sewall: 1674-1729. V. 1 [-3], Massachusetts Historical Society
- Knight, Sarah Kemble, 1666-1727. The private journal of a journey from Boston to New York in the year 1704, Frank H. Little, 1865.
- 1773-1774 Journal kept by Hugh Finlay, Surveyor of the Post Roads on the Continent of North America
- Jenkins, Stephen, 1857-1913. The Old Boston Post Road. New York: G. P. Putnam’s sons, 1913.
- Marlowe, George F. The Old Bay Paths. New York: Hastings house, 1942.
- O’Connell, James C. Boston and the Making of a Global City, University of Massachusetts Press (2025)
- Gallagher, Winifred. How the Post Office Created America: A History, 2016.
- Fuller, Wayne E. The American mail: enlarger of the common life, University of Chicago Press, 1972.
- U. S. DEPARTMENT OF AGRICULTURE OFFICE OF INFORMATION PRESS SERVICE, “United States Route No. 1 is a Highway of History,” October 9, 1927.
- Bahne, Charles. “Milestones of Greater Boston, Then and Now,” Boston 1775, 2012.
- Photos, map, and history of NYC’s Boston Garden
- Our header image is by Carl Rakeman and is in the public domain
Related episodes to check out
- The 1689 Uprising in Boston (episode 165)
- Granite, Glass, and the Construction of King’s Chapel (episode 279)
- A Constitutional Culture: New England and the Struggle Against Arbitrary Rule in the Restoration Empire, with Professor Adrian Chastain Weimer (episode 295)
- The Dread Pirate Rachel (episode 147)
- America’s First Christmas Cards (episode 316)
Automatic Shownotes
Chapters
| 0:13 | Introduction to Boston’s Post Road |
| 1:33 | Acknowledging Supporters |
| 3:29 | Landmarks of Boston |
| 7:32 | The First Post Office |
| 10:43 | The First Official Postal Carrier |
| 15:21 | Challenges to Mail Service |
| 16:35 | Sarah Kimball Knight’s Journey |
| 22:17 | The Role of Milestones |
| 25:00 | Washington’s Journey |
| 28:24 | The Legacy of U.S. Routes |
| 31:58 | Tracing Washington’s Route |
Transcript
Jake:
Welcome to Hub History, where we go far beyond the freedom trail to share our favorite stories from the history of Boston, the Hub of the Universe.
Introduction to Boston’s Post Road
Jake:
This is episode 352, Boston’s 17th century interstate system. Hi, I’m Jake. This week, I’m talking about America’s first interstate highway, or perhaps inter-colony highway system linking Boston to New York City. The 17th century Boston Post Road is often overlooked in the city’s early history, but it marked the earliest and one of the most ambitious attempts to knit the fragmented English colonies of North America into a single, cohesive entity. From Boston’s first post office, which accepted only overseas letters, to the post riders who braved mountainous passages and roaring rivers, this primitive road network was the original interstate, forged not just for convenience, but for the survival of the English colonial project.
Jake:
In this episode, we’re hitting the road to explore how the Boston Post Road evolved from an indigenous trade route into the King’s Highway, a crucial artery for colonial and early federal correspondents. We’ll trace the paths of the Upper Route through the Wilderness of Central Mass in Connecticut and the lower coastal alignment of the post road that shaped the roads and transportation networks of modern New England.
Acknowledging Supporters
Jake:
Along the way, we’ll uncover the stories of a few people who marked the miles, from wealthy landowners like Paul Dudley, to determined travelers like Sarah Kimball Knight, to George Washington, who arrived in Boston for his first official visit as president along the Boston Post Road.
Jake:
But before we talk about the old Boston Post road, I just want to pause and say thank you to our latest financial supporters. I always say that I appreciate both listener supporters who give one-time contributions to the show and supporters who commit to monthly support.
Jake:
This week, we have some of both to thank. Listeners Victoria W., Emily M., and Eric B. All gave one-time gifts on PayPal, which will help with one-off expenses, like the new headphones I’m going to have to buy for editing and mixing the podcast, after the ones I originally bought when we started this show almost 10 years ago finally broke fully in half. At the same time, Ryan P. and Mark N. just signed up to provide ongoing monthly support on our Patreon. That ongoing support pays for the ongoing costs of producing this show. Costs like podcast media hosting, web hosting and security, our AI transcription and mastering service, and the research databases I pay for access to. Without the support of our listeners, I wouldn’t be able to make Hub History. So to Mark, Ryan, Eric, Emily, Victoria, and all our supporters, thank you. If you’re not yet supporting the show and you’d like to start, it’s easy. Just go to patreon.com slash hubhistory or visit hubhistory.com and click on the Support Us link. And thanks again to all our new and returning sponsors.
Landmarks of Boston
Jake:
I’m going to start out this week’s episode with two landmarks. The first is Boston Garden. And no, I don’t mean the TD Garden, or the old Boston Garden, or even the Boston Public Garden. The Boston Garden I’m talking about is a tiny park in the faraway Bronx. It’s a triangular grassy patch with two small trees and some scraggly shrubs, about 60 feet on the long side and about 40 feet on each small side. It’s bounded by Bronxwood Ave, Allerton Ave, and Boston Road.
Jake:
Over 200 miles away, our other landmark is a stone in Roxbury’s John Elliott Square, where Roxbury Street, Dudley Street, and Sinner Street intersect. Set tight against the brick facade of a storefront that’s right in the elbow where Sinner and Roxbury part ways, there’s a granite obelisk about two feet tall with an inscription on the front that says, The Parting Stone, 1744, P. Dudley. If we were standing on this corner in 1744, the right fork, up Roxbury Street, would lead us to Harvard Square, then out through Watertown, past the famous Wayside Inn in Sudbury, eventually to Springfield, and then down the Connecticut River to Hartford, New Haven, and onward to New York City. The left fork down Center Street would wind its way through Dedham, across the Rhode Island state line at South Attleboro, into Connecticut and through New London to New Haven, and eventually into the Bronx, past the corner that’s now marked with a small sign designating it Boston Garden. The older, northerly route connecting the two landmarks originally ran from the Battery in Manhattan to the old Statehouse in Boston. This was one of the first and most ambitious highways in what’s now the United States, known when it was first designated in 1673 as the Boston Post Road.
Jake:
By the late 17th century, almost a half-century after Boston was founded by John Winthrop and his Puritan Arbella fleet, the capital of New England was surprisingly better linked to England and the rest of Europe than it was to the other colonies along the eastern seaboard of North America. In his book, Boston and the Making of a Global City, James C. O’Connell notes, From its beginnings, Boston was situated in a global communications network. As the colonial economy strove to find trade outlets for its commodities, information had to be exchanged. Sea captains would carry mail, which included political and business news. Ship journeys from England took at least six weeks and often many more depending upon the weather. In 1639, only nine years after Boston’s founding, the General Court of Massachusetts designated to the port’s first postmaster, Richard Fairbanks.
Jake:
It cost one penny, usually paid by the sea captain delivering a letter from England to deposit a letter with the postmaster. Missives from government officials were carried gratis. Fairbanks owned a tavern at the foot of Long Wharf. When ships arrived from London and the Caribbean islands, merchants and other interested people would gather at his tavern to read the mail and share relevant news. This was British America’s first post office.
Jake:
That first post office was, however, almost entirely outward-facing. The 1639 statute appointing Fairbanks’ postmaster notes, His house in Boston is the place appointed for all letters which are brought from beyond the seas, or are to be sent thither, which are to be brought to him, and he is to take care that they be delivered, or sent according to their directions.
The First Post Office
Jake:
No mention is made of letters that might be brought from or sent to someone on this side of the seas. As the series of English colonies along the coast grew, the need for an internal post system grew along with it, becoming acute in 1664. In that year, four English frigates sailed into the harbor at New Amsterdam during peacetime and demanded the city’s surrender. After the ensuing Anglo-Dutch War ended with the Dutch defeat, the city was formally ceded to England, and its name was changed to New York.
Jake:
Now, on paper at least, England controlled colonies stretching from New France, across the main frontier in the north, to New Spain, across the frontier south of Charleston in the province of Carolina. If one of those neighboring powers, with their vast naval might, were to declare war on England, it would be imperative for the English colonies to be able to exchange letters, intelligence reports, and even troops over land, in case the coast was blockaded. To that end, Winifred Gallagher describes the earliest attempts to link the colonies by land in her book, How the Post Office Created America. Great Britain’s gradual, modest improvements to the colonial post were primarily motivated by the need to inspire some political asperite decor among her quarrelsome children, whose culture clashes threatened her struggle with France over control of North America.
Jake:
In 1650, the crown optimistically ordered its provincial governors to start building a king’s highway between Boston and Charleston, South Carolina, In 1673, Francis Lovelace, the governor of New York, responded to King Charles II’s wish that his American subjects enter into a close correspondency with each other, With the former New Amsterdam in English hands, and the king urging his American subjects to enter into a closer correspondency, Wayne Fuller describes in his book The American Mail how Governor Francis Lovelace of New York dispatched the first official postal carrier toward Boston.
Jake:
With great expectations, Governor Lovelace sent a postman off to Boston in 1673 with a number of mailbags, each designated for a particular town along the way, and a letter to Massachusetts Governor, John Winthrop.
Jake:
Now, this is a mistake that I’ve seen repeated in a lot of the books and articles that I checked out in preparation for this episode. The recipient of the letter I’m about to read from was not Massachusetts Governor John Winthrop. The founding governor of the Bay Colony had been dead for 24 years by that point. The John Winthrop who received this letter was his son, John Winthrop the Younger, who was governor of the Connecticut Colony at the time. The letter from Governor Lovelace said, I here present you with two rarities, a packet of the latest intelligence I could meet with and a post.
The First Official Postal Carrier
Jake:
By the first, you will see what has been acted on the stage of Europe. By the latter, you will meet with a monthly fresh supply, so that if it receive but the same ardent inclinations from you, as at first it hath from myself, by our monthly advisos, all public occurrences may be transmitted between us, together with several other great conveniences of public importance, consonant to the commands laid upon us by his sacred majesty, who strictly enjoins all his American subjects to enter into a close correspondency with each other.
Jake:
That same letter outlined the expectation that a courier would leave New York on the first Monday of every month, and he would be expected to return to New York before the month was over. In his 1913 History of the Boston Post Road, Stephen Jenkins describes how that first courier completed a successful round trip, arriving in Boston from New York around the first week of February 1673, and then returning. Two weeks after his departure from New York, he rode through Roxbury into Boston, over the narrow neck connecting the mainland with the Tri-Mountain Peninsula, where he delivered his mails and received congratulations on the success of his journey. Two days of rest, perhaps, and then the return journey began, for he must be back within the month. It was wintertime, and he was not delayed by the smaller streams, for they were frozen over. The larger ones he crossed by ferries. Within the month, he rode into the fort at New York and turned his mailbags over to the secretary.
Jake:
The letter from New York Governor Lovelace concludes, I shall only beg of you your furtherance to so universal a good work, that is to afford him directions where and to whom to make his application to upon his arrival in Boston, as likewise to afford him what letters you can, to establish him in that employment there. It would be much advantageous to our design if, in the interval, you discoursed with some of the most able woodmen to make out the best and most facile way for a post, which, in the process of time, would be the king’s best highway, as likewise passages and accommodations at rivers, fords, or other necessary places.
Jake:
The able woodman of Massachusetts marked the most facile way for a post, with the king’s sign, a broad arrow hacked into tree trunks along the way. This first attempt at establishing the king’s best highway between Boston and New York followed existing overland routes wherever possible. That meant that for much of its journey through Massachusetts, it used a path that indigenous nations had used for trade between the Connecticut River Valley and the Massachusetts Bay for generations. A trail that was known to early Puritan colonists as the Bay Path. Crossing the Charles over the bridge in Watertown Square, this path went out through Watertown and Waltham along Route 20, through Weston, eventually getting to Weyland. In a 1942 book about this old Bay Path, George Marlow describes where it went from there. The Bay Path, leaving Weyland, took a wide sweep westward, passing through Sudbury, Stowe, Lancaster, Princeton, Brookfield, Warren, Brimfield, and on to Springfield, and later south to Hartford. A continuation of this path crossed the Connecticut at Springfield and led into the Iroquois country in New York. The foundation seemed to be well laid for regular monthly mail service between the major cities of English America, commencing in early 1673.
Jake:
However, events outside the control of the post office interfered, and Winifred Gallagher’s account of this first experiment with the Postal Service concludes, This service was interrupted just six months later, when the Dutch briefly retook the large territory along the Hudson and Lower Delaware rivers that they called New Netherland.
Jake:
The Dutch recaptured the city that they called New Amsterdam in August 1673, but the Treaty of Westminster that ended the war returned it to the English.
Jake:
The English then sent a new governor named Edmund Andros, who assumed control of the colony in November 1674. You can learn more about how Andros, the royal governor of New York, became the scourge of Puritan Boston in Episodes 165, 279, and 295.
Challenges to Mail Service
Jake:
When Andros took over, officials in both cities tried to start the mail service back up, but just a few months later, King Philip’s war broke out, rendering the wilderness of western Massachusetts and Connecticut a no-go zone for post-rioters and nearly forcing the English colonial project back into the sea. The New England colonies barely survived this war, and slowly began to recover to the point where their leaders could once again consider a regular correspondence with colonies to the south. James O’Connell describes how mail service to New York was restarted over a decade after the war, in Boston and the making of a global city. By the 1690s, colonial governments introduced formal mail service, first by a private franchise, later under crown control. The service resembled the later Pony Express, with post riders galloping from station to station, usually inns. It took a week to travel between the two cities. By 1729, there was weekly mail delivery at 13 post offices between Boston and Philadelphia.
Jake:
The service developed quickly between the 1690s and the 1720s.
Sarah Kimball Knight’s Journey
Jake:
While a post-rider in 1629 could count on graded roads and official stone markers to guide the way, along with cozy inns to dine in, the post-road was still more of a suggestion than a reality when postal service to New York was restarted in the 1690s. Even a decade later, when Madam Sarah Kimball Knight, a wealthy 39-year-old widow from Boston, set out on her way to New York, Winifred Gallagher writes, She had no choice but to do the 268-mile business trip on horseback, as the rough highway could not accommodate carriages.
Jake:
Knight kept a journal of this trip, which I’ll link to in the show notes this week. In it, she describes how she rode from Boston to Dedham and spent the night in an inn, meeting the post rider who was heading west along the post road the next morning, being October 3rd, 1704. With her guide, it took Knight four days to get to New Haven, which Winifred Gallagher summarizes in her book. She rode in the company of a crown post rider. Knight’s observations about the roads, quote, very bad, encumbered with rocks and mountainous passages, which were very disagreeable to my tired carcass, are the more noteworthy for occurring in the colony’s most populous, settled region, on their best approximation of an interstate. On a typical day of traveling with the post, she choked down a dismal meal in an inn on the route. What cabbage I swallowed served me for a cud the whole day after, then followed the mail courier to a roaring river. There being no bridge, he dutifully got a lad in a canoe to ferry her across, then raced off towards his next relay stop some fourteen miles away.
Jake:
After the hard riding of this first leg of her journey, Madame Knight stayed in New Haven until early December, conducting some business and collecting some debts, before setting out again on December 6th and taking another four days to get to New York. You can follow her entire adventure in her journal.
Jake:
A quarter century later, the raging rivers were bridged or forded, and a series of inns provided food and lodging for weary post riders.
Jake:
An inset node on a map of New England in a 1729 British atlas explains the arrangement of these 13 post offices, and the routes that the post riders would take as they rode from end to end. The account starts at the western terminus of this early post office system. The western post sets out from Philadelphia every Friday, leaving letters at Burlington and Perth Amboy, and arrives at New York on Sunday night, the distance between Philadelphia and New York being 106 miles. The post goes out eastward every Monday morning from New York and arrives at Saybrook Thursday noon, being 150 miles, where the post from Boston sets out at the same time. The New York Post returning with the eastern letters and the Boston Post with the western bags are dropped at New London, Stonington, Rhode Island, meaning Providence, and Bristol. The post from Boston to Piscataway, being 70 miles, leaves letters at Ipswich, Salem, Marblehead, and Newberry. There are offices kept at Burlington, Perth Amboy in New Jersey, New London and Stonington in Connecticut, at Rhode Island, Bristol, Ipswich, Salem, Marblehead, and Newberry, and the three great offices are at Boston, New York, and Philadelphia.
Jake:
From that description, you’ll note that the post riders no longer turned north at New Haven to find their way to Hartford and pick up the old Bay Path to Boston. Instead, they followed a new coastal alignment of the post road that took them through Rhode Island, up to Dedham, and into Boston from the south rather than from the west. The new network encompassed a longer route on a shortened schedule, with Winifred Gallagher noting that the new centralized network link New Hampshire, Massachusetts, Connecticut, New York, and Pennsylvania on a weekly basis. A study of how to make the mail in New England faster and more efficient, undertaken in 1774 by the last British postal surveyor of the region, describes the coastal route of the Lower Post Road from Boston as far as Newport.
Jake:
Peter Mumford’s ride from Boston to Newport is 80 miles, passing through Providence, Warren, and Bristol, for which service he is obliged to keep three horses and is paid 40 pounds sterling per annum. He should leave Boston at 3 o’clock Monday afternoon, but I’m told that it is 5 or 6 ere he takes his horse. He arrives at Providence, 45 miles, at 9 o’clock the next morning, and at Newport, 35 miles farther, at 5 o’clock in the evening of Tuesday. On his return from Newport with the Western Males, he leaves that office on Friday, half-past 2 p.m., passing through Bristol and Warren, he arrives at Providence between 7 and 8 o’clock Saturday morning. He leaves it at 9 and arrives at Boston at 6 in the evening in fine weather. Thus, 26 hours are required to ride 80 miles.
Jake:
With the introduction of weekly mail service, both the new Lower Post Road and the original Upper Post Road became increasingly important in tying New England together.
The Role of Milestones
Jake:
This growing cultural relevance made some of the most wealthy people in the colony want to add their names to the post roads. And Paul Dudley, a rich lawyer, Roxbury landowner, and the namesake of the former Dudley Square, started placing milestones along the road in 1729. In a 2018 blog post, historian Charles Bainey noted, Most of the stones in the immediate Boston area were erected by prominent political figures, such as Paul Dudley. I’m guessing that those men saw the milestones partly as a public service, and partly as a billboard advertising their beneficence, just as we see signs near highway construction projects that give the names of government officials today.
Jake:
Tourists are often told that these milestones measure the distance from the so-called Boston Stone, an old millstone that’s set in a brick wall on the Blackstone Block, next to the Haymarket. There’s no evidence that the Boston Stone was ever mile zero for the Boston Post Road, but a 1707 diary entry from the Reverend Samuel Sewell makes a strong argument that the old State House, still known in 1707 as the Town House, was always the starting point of the post roads. The minister wrote, Mr. Antrim and I measured with his wheel from the townhouse two miles and drove down stakes at each mile’s end in order to place stone posts in a convenient time.
Jake:
As far as I know, any milestones placed by Samuel Sewell in 1707 are long gone. And Charlie Bainey speculated that the first three milestones placed by Paul Dudley in 1729 were dug out by Continental soldiers and used to reinforce the 1775 siege lines. But you can still pick up the trail, starting with the fourth mile, which is set in the brick wall in front of the Mission Park Development along Huntington Ave and Mission Hill. The fifth mile is marked by a stone on Harvard Street in Brookline, in front of the United Parish Church. The sixth and seventh milestones are both in Brighton, on the way to Harvard Square along Harvard Ave. These four surviving stones are inscribed with the number of miles to Boston, the date 1729 when they were placed, and the initials PD for Paul Dudley. Dudley’s Parting Stone, where we started today’s episode, was placed later, in 1744, and it doesn’t mark a mile, but rather the point where the Upper Post Road and the Lower Post Road parted ways, not to meet again until they got to New Haven.
Washington’s Journey
Jake:
From the 1720s to the 1760s, other wealthy benefactors paid to mark 99 miles along the Upper Post Road from Boston all the way to Springfield, with 47 surviving today.
Jake:
When George Washington visited Boston in 1789 as part of his New England tour, an event we touched on briefly in episode 147 about the so-called pirate Rachel Wall, most of his journey from the U.S. Capitol in Manhattan followed the route of the Lower Post Road. This route was also marked by stone mile markers, a few of which still survive today. Even more were still standing in December 1885, when a Boston Globe reporter retraced the route of the Lower Road, which the author noted used to be called the Dedham Road until some 50 years ago, when they thought that name wasn’t good enough and called it Sinner Street. The original layout of Sinner has been interrupted and rerouted by the construction of Columbus Ave, the Southwest Corridor, the original alignment of U.S. Route 1, and the Arbor Way, but we can still follow the reporter’s journey. He found the three-mile stone 100 yards from the parting stone, quote, on the other side of Sinner Street, opposite No. 5, where Louis Prang resides. Louis Prang was the chromolithographer who created America’s first Christmas cards and the subject of episode 316 of this podcast. The stone still stands, set into a stone wall in front of the John Elliott Square urban wild.
Jake:
The fourth mile is marked by a much smaller and more unassuming stone wedged into a wall in Hyde Square, which, in 1885, was so easily overlooked that a passerby after dark need not be surprised if he stumbles over it and keeping too close to the fence. Our anonymous author notes that Milestone 5 on the Lower Post Road was founded Jamaica Plain, nearly opposite the West Roxbury Soldiers Monument and facing Center Street at the corner of Elliott Street. This stone was evidently intended to be Judge Dudley’s masterpiece. It’s three feet nine inches high and more pretentious in every way than his two predecessors. The inscription, which you can still read at the corner where South Street forks away from Center Street in J.P., reads, Five Miles Boston Townhouse, P. Dudley Esquire, 1735. Our reporter continues, The word miles at the top is carved at one side, the five standing in the middle of the line as if the miles was a happy afterthought when the rest of the work was finished. The modern equivalent of these milestones stands in Kenmore Square, where a green highway sign bolted to a lamppost marks the beginning of U.S. Route 20 and notes that it’s 3,365 miles to Newport, Oregon.
Jake:
It only makes sense that when the federal government created the first nationwide system of numbered highways, both the upper and lower Boston post roads became key spokes radiating out from Boston’s hub. The upper post road, the oldest highway in America, is today the longest.
The Legacy of U.S. Routes
Jake:
U.S. Route 20 was designated 100 years ago on the same day that the more famous Route 66 was designated in 1926. Crossing 12 states all the way from Boston to the Pacific Ocean in the small town of Newport, Route 20 barely edges out Cape Cod’s Route 6 as the longest highway in the country. The Lower Post Road has a designation that’s no less famous, U.S. Highway 1. Today, Route 1 stretches from Key West to the Canadian border in Maine, including the original section that connected the Battery in Manhattan to the old Statehouse in Boston.
Jake:
While U.S. Route 1 was also officially designated a federal highway in 1926, several sections of the Atlantic Coast Highway in New England had already had signs naming it as Route 1 for years.
Jake:
A 1927 U.S. Department of Agriculture press release promoting travel on the newly laid-out highway reads, Stretching from end-to-end of the 13 original colonies, from Fort Kent, Maine, to Miami, Florida, the connecting sections of the Atlantic Coast Highway, known as United States Route No. 1, have formed a highway of history for 300 years. Washington traveled it repeatedly in peace and war. Now, the 94-mile section between New York and Philadelphia carries a heavier average traffic than any other road of equal length in the world. Route No. 1 connects New York, Princeton, and Philadelphia, the three cities at which the capital was established in the early years of the Republic. With Washington, the final choice. And it passes near or through nearly all the revolutionary battlefields and many of those of the Civil War. Both the upper and lower alignments have been more recently absorbed into the interstate highway system. You can pull up a wide view of New England on Google Maps and instantly see that the upper and lower post roads very roughly followed the routes of the Mass Pike and I-91 on the upper alignment and I-95 along the coast on the lower alignment.
Jake:
When newly elected President Washington came to Boston in 1789, he followed the lower post road into Massachusetts at South Attleboro. You can follow his route by tracing Washington Street and the original alignment of Route 1 through North Attleboro, Sharon, Walpole, and Westwood. From Westwood, President Washington took some streets that are intimately familiar to me before arriving at Milestone No. 5 in Jamaica Plain. I live in the Reedville neighborhood of Hyde Park, so I run a lot of my errands in Boston’s southern suburbs, especially Dedham. In the Islington neighborhood of nearby Westwood, President Washington would have turned right from what’s now Washington Street onto East Street, right by my barbershop. He followed East Street around the marshes that still line Wigwam Pond in Dedham into Dedham Square, where I ran a 10K earlier on the day of this recording.
Jake:
There, you cross the alignment of modern Washington Street onto Sinner Street. Following Sinner Street into Boston today, you pass the oldest remaining house in the city, just after the Boundary Stone marking the town line near Temple Beth Israel Cemetery. Then you pass the gravel pit in West Roxbury, go through the Holy Name Rotary, pass into Jamaica Plain, and eventually find your way to the Parting Stone in Roxbury, where our story began.
Tracing Washington’s Route
Jake:
From there, Washington’s route took him into Nubian Square, which used to be named for Paul Dudley. After Nubian Square, Washington’s journey joined streets that have been renamed in his honor, following what’s now Washington Street through Lower Roxbury and the South End to the Theater District and on to the old State House, which was mile marker zero for the Boston Post Road.
Jake:
To learn more about the Boston Post Road, check out this week’s show notes at hubhistory.com slash 352. I’ll have links to all the sources we used this week, including the 1885 Boston Globe article describing a journey to locate Dudley’s milestones, and Charlie Baney’s blog post about those same milestones. I’ll link to the books How the Post Office Created America by Winifred Gallagher, The American Mail by Wayne Fuller, Old Bay Paths by George Francis Marlowe The Old Boston Post Road by Stephen Jenkins and Boston and the Making of a Global City by James O’Connell. I’ll also have links to online copies of the journals kept by Samuel Sewell, Sarah Kimball Knight, and Hugh Finley of the Royal Mail that I quoted in the episode. Plus, there’ll be historic maps showing the routes to the Upper and Lower Post Roads, and images of a few selected milestones.
Jake:
If you’d like to get in touch with us, you can email podcast at hubhistory.com. I still have profiles for Hub History on Facebook, Twitter, and Instagram, and over on Mastodon as at hubhistory at better.boston. These days, though, your best bet for getting in touch with me via social media is Blue Sky, which is pretty much the only place where I regularly post and interact with people. You can find me on Blue Sky by searching for hubhistory.com. If you’re not spending much time on social media these days, the easiest way to get in touch with us is to go to hubhistory.com and click on the Contact Us link. While you’re on the site, hit the Subscribe link and be sure that you never miss an episode. If you subscribe on Apple Podcasts, please consider writing us a brief review. If you do, drop me a line. I’d love to send you a Hub History sticker as a token of appreciation. That’s all for now. Stay safe out there, listeners.





