Office of State History

Daring Revolutionary War spy Enoch Crosby, who bedeviled the British in Putnam and Westchester counties, is perhaps the most famous of the Town of Southeast’s elected officials.

Crosby was Southeast supervisor in 1812-13 and is believed to be the model for Harvey Birch, the main character in James Fenimore Cooper’s “The Spy.”

At a time when both counties were hotbeds of Revolutionary War activity just to the north of British-occupied New York City, Crosby was a double-agent. 

He posed as a British spy to pass on intelligence to the Americans and was in and out of some terrifying tight spots, plying his skills as far north as Lake Champlain. Spycraft, as a rule, is and was a dangerous trade -- especially for a 26-year-old former shoe cobbler.

But real-life spy Crosby, from all reports, was every bit as sly and silver-tongued as the fictitious Harvey Birch

His nimble wit and political savvy gained him access to Westchester and Manhattan Tories whose words and schemes were soon reported to American patriots — skills that no doubt helped him in his civic and political campaigns after the war.

One alleged hair-raising escape took place near the Carmel-Kent border along what is now Route 301. There, Crosby found himself jumping out the back window of a farmhouse and fleeing into the woods as musket-and-bayonet armed redcoats burst through the front door.

Fortunately for Crosby, the nearby home of Militia Col. Henry Ludington served as a safe-house and hideout when he was on the run. 

The colonel’s daughter, Sybil, is of course famously known as the female Paul Revere for her legendary 40-mile horseback ride to round up local militias to ambush 1,800 British troops on their return from burning homes and American supplies in Danbury, Connecticut, on April 26, 1777.

Crosby, who came from a poor family, worked as a humble shoemaker in Kent and Danbury before the war, so the torching of that city may well have helped spur him to join the rebels.

After the war, Crosby bought land in Southeast near the Carmel border and he served as a justice of the peace and associate judge before his election as Southeast town supervisor. He took office just in time for the nation’s second martial engagement with the Brits — the War of 1812.

Little is known about Crosby’s tenure as town supervisor because the records from that era were destroyed in a Southeast Town Hall fire in Brewster village later in the 19th century (the town is better known as “Brewster” as well).

Crosby’s colonial-style farmhouse, built in 1789, still stands by the side of Enoch Crosby Road, not far from Route 6 in Southeast-Brewster.

Born in 1750, Crosby died in 1835 and is buried in nearby Carmel’s Gilead Cemetery.