In Revolutionary days, the Boston Post Road was Manhattan’s main highway. This mail route began at the island’s southern tip, ran along today’s Park Row and Bowery, zigzagged up the east side, entered what’s now Central Park around 97th Street, and followed parts of St. Nicholas Ave. and Broadway toward The Bronx. From there it continued to Boston through New Haven, Conn.
The passage of the Stamp Act by Britain in 1765 united the colonies along the Post Road like nothing before it. The law forced American printers to use special, expensive paper — stamped with a royal imprint — for newspapers and other documents. Opposition to this tax erupted in publications across the northeast, and mail riders carried the fighting words from town to town along the Post Road.
The boldest critic, writing under the name “Cato,” taunted the throne in New Haven’s newspaper, the Connecticut Gazette. Cato called Americans “brethren” and Englishmen “foreigners.” He challenged the allegiance of the agents who had agreed to enforce the Stamp Act in America. In Cato’s opinion, these men should have “bravely refused to become instrumental in enslaving his country.”
Patriots along the Post Road agreed, and soon words turned into threats. One by one, British-appointed stamp agents between Manhattan and the Bay resigned in fear. New York’s stamp master, James McEvers, quit after some of Cato’s letters were reprinted in Manhattan’s New York Gazette.
Britain pushed its tax on the Americans anyway. In late October 1765, the New York Gazette learned that stamped paper had been “privately” shipped to Manhattan. In response, on Nov. 1, an angry mob stormed Bowling Green and burned an effigy of New York’s royal governor, Cadwallader Colden. Terrified by the Post Road’s “inflammatory” newspapers, Colden refused to unpack the stamped paper and was relieved of his position.
From then on, leading patriots between New York and Boston — dubbed “Sons of Liberty” — kept in touch through illegal “committees of correspondence” that exchanged messages along the Post Road. On Dec. 17, 1773, for instance, the morning after the Boston Tea Party, Samuel Adams wrote a note to New York’s Sons of Liberty, informing them of the previous evening’s “interesting event.” He sent the message to Manhattan in the hands of an express rider named Paul Revere.
After the Tea Party, Britain clamped down on the mail system. Ben Franklin was dismissed as America’s deputy postmaster general, and anyone else considered “too much of an American” was also replaced with postal officers loyal to King George.
Franklin feared for the safety of rebellious messages sent along the Post Road “through the hands of such officers.” In a letter to Boston’s leaders, New York’s committee of correspondence expressed concern that its “secrets are in the hand of Government” and that “our News Papers in a time of public danger may be stopped.”
Immediately a printer named William Goddard began a crusade to free the colonial mail from Britain’s grip. Goddard knew the Post Road well; he had launched the Providence Gazette and served as town postmaster. Now he wanted to start a “constitutional” mail system with patriotic American post riders.
In February 1774, Goddard traveled the Post Road to sell his plan. Manhattan’s Sons of Liberty quickly agreed, as did leaders in Post Road towns of New Haven, New London, Conn., and Providence. In Boston, Samuel Adams loved the idea. Revere called it “one of the greatest strokes our Enemies have mett with (except the late affairs of the Tea).”
“Constitutional” messengers indeed came through at the hour of need. On the morning of Apr. 19, 1775, an express rider left Watertown, Mass., and traveled the Post Road toward New York with word of fighting in Lexington. In each town along the way, committees of correspondence signed off after receiving the news.
By Apr. 23 the details reached Manhattan. Fourteen milestones, planted along the Post Road in 1769, guided the rider down the island. (Franklin introduced these stones as a way to calculate postage.) The 3 Mile stood just north of today’s Madison Square Park. The 2 Mile, at Astor Place. The 1 Mile, where Bowery meets Canal Street.
After receiving word of Lexington, New York’s Sons of Liberty rioted on Manhattan. They busted into a British arsenal and passed out weapons in the streets. They seized mail from English postal officers. “They received the news with avidity,” noted Thomas Jones, a royal official. “They had wished for it for a long time.”
In September 1776, the American army lost Manhattan to a British attack. On the eve of battle, General George Washington was headquartered along the Post Road, at modern 161st Street and St. Nicholas Avenue, today site of the Jumel Mansion. The British landed warships at Kip’s Bay, in the East River. They stormed the island and captured the “Main Road,” as Washington called the Post Road, with little resistance.
When Washington saw the cowardice of troops defending the Main Road, he grew furious and wondered aloud whether he could win the war. General Nathaniel Greene later described Washington in this moment of despair as having “sought death rather than life.”
A valiant blockade positioned along the Post Road at McGown’s Pass, in modern Central Park, kept the Americans from total defeat. Washington rallied his men for fighting the following day at Harlem Heights. This time the freshly inspired troops held their ground.
Washington retreated to the mainland, leaving Manhattan in British occupation, but the morale of American troops had been restored. General George Clinton, who later became New York’s governor, considered the stand at Harlem Heights “almost equal to Victory” and felt it gave soldiers “new Spirits” to fight on.
Fight on, and win, they did. On Nov. 25, 1783, “Evacuation Day,” the British relinquished Manhattan to the victorious Americans. Washington and Clinton paraded down the Post Road that morning. Seven years earlier, on this very same highway, the idea of freedom had seemed bleak. Come Evacuation Day, these men may have felt — as Americans remind themselves every July 4 — that success is sweeter after a struggle.
Eric Jaffe is author of “The King’s Best Highway: The Lost History of the Boston Post Road, the Route That Made America” (Scribner).