In July of 1636, John Oldham’s boat was discovered off the coast of Block Island, RI. There was only one passenger: Oldham’s naked corpse, with a hatchet lodged in his skull.
An adventurer and a rake, whose death at the hands of a member of the Narragansett tribe may have been retribution for having caused a smallpox outbreak, Oldham was murdered three years after he made big colonial news. Traveling on foot from Cambridge, MA, into the wilderness of Connecticut at a time when long-distance travel happened almost entirely by boat, his passage sparked interest in overland travel, and, though he wouldn’t live to see it, his path would form the template for the most important route in New England, one that would connect Beantown and the Big Apple with the Elm City: the Boston Post Road.
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Exactly when it got that name isn’t clear, but, decades later, by which time the road was formed and in use, Oldham’s mantle was picked up by Francis Lovelace, the governor of New York. Where Oldham depended on brawn and rascal’s luck, Lovelace was a dandy royalist—the brother of Richard Lovelace, the cavalier poet best known for the closing stanza of To Althea, from Prison: “Stone walls do not a prison make / Nor iron bars a cage”—who presided over an exclusive social club in New York, and was convinced that an efficient postal service was a necessity for the health of the colonies. In 1673, he began sending the colonies’ first regular postal carriers over the route, making it a literal post road.
Today, the Boston Post Road goes by many names on its long trip from New York to Boston. In New Haven alone, the road becomes Columbus Avenue at Ella T. Grasso Boulevard, then goes through a dizzying series of four more names before it hits East Haven.
It may be hard to imagine that the Post Road—which, in New Haven anyway, is overshadowed by more bustling turnpikes and surface streets—was once the vital artery that connected the city to the rest of New England. Among other things, it brought news and commentary to and from New Haven, spreading its potent brand of revolutionary sentiment across the land.
New Haven’s anti-royalist bent had been simmering for 130 years. The purest of the Puritan colonies, it was founded in direct resistance to British authority. Later, even as the trade they needed to become prosperous had become impossible without a royal charter, many New Haveners fought tooth and nail to remain independent from the chartered Connecticut Colony. Despite losing that battle in 1664, the people of New Haven remained fiercely suspect of outside influence, a suspicion that flared into a newsprint revolt after the much-pilloried Stamp Act was passed in 1765.
If it weren’t for the Boston Post Road—and one of its most famous travelers, Benjamin Franklin—New Haven’s place in the conversation would have been far smaller. After becoming the joint postmaster general of the colonies in 1753, Franklin found the Post Road in shambles, run down by heavy traffic and no oversight. He set out on a tour of the route, landing on New Haven as the best location to build the first of several new post offices, complete with a printing shop. In the spring of 1755, in a building near Yale, the colony’s first newspaper, The Connecticut Gazette, began publishing.
Franklin turned the postal system around in less than a decade, and the Post Road with it. It became a vital trafficker of ideas throughout the colonies, communicating news, mail and—crucially—profits. The British Crown, swamped by debts, took notice and passed the Stamp Act in a bid to recoup some of its expenses.
More than fire, more than flood, more than backbreaking labor and swamps and failed crops, the colonists hated taxes. In New Haven, especially, there was a brisk, brutal backlash to the Stamp Act. The Gazette, which had been dormant for several years, flared back into existence in July 1765 under Benjamin Mecom, Franklin’s firebrand nephew. The first issue Mecom printed, which is currently stored in Yale’s Beinecke Rare Book & Manuscript Library, is topped with this quote adapted from Shakespeare’s Julius Caesar: “There is a Tide, in the Affairs of Men / Which, taken at the Flood, leads on to FREEDOM.” In the original, the last word is “fortune.”
Mecom’s sentiment was representative of most of the city at the time. New Haven’s population had boomed to 15,000 people, and the economy was bolstered by independent trade with the West Indies. Yale students, lit by youthful liberalism, mingled with the old guard of the city—those who weren’t so far removed from New Haven’s early struggles to remain independent. In the middle of it, Mecom weaponized the Gazette to fight a war of ideas against British taxation.
The Boston Post Road, meanwhile, carried the paper’s inflammatory news and commentary across the Eastern seaboard. As Eric Jaffe says in his book The King’s Best Highway (2010), “It was at his Connecticut Gazette print shop located in the New Haven post office—not at the meetinghouse or during sessions of the legislature—that the strongest political jabs of this volatile era were exchanged.”
New Haven sent native son Jared Ingersoll to England to argue against the Stamp Act. But when he returned as the Crown’s chief stamp tax collector, the beleaguered civil servant found himself derided “as a kind of fiend with a cloven foot and fury-forked tongue, a Court Parasite & a Lover of the Stamp Act,” as he says in a 1765 letter—or x“confoundedly begad & beswompt, as we say in Connecticut.” Parliament repealed the Stamp Act the following year, thanks in part to Mecom’s fiery rhetoric and the political pressure that could be mustered thanks to a single long thoroughfare.
The Boston Post Road, conceived for simple freedom of motion, had become about a different sort of freedom entirely.
Written and photographed by Sorrel Westbrook.
