Secrets on the Washington Spy Trail

Found Only On Long Island’s North Shore


Abraham Woodhull, Benjamin Tallmadge and Caleb Brewster were friends turned patriot spies from the North Shore of Long Island, whose lives were dramatized in “Turn,” the spring 2014 AMC television series on the Culper Ring. They and other colonists are immortalized today in their families’ preserved homes and re-enacted daily activities for everyone to experience.

A visit to the North Shore takes one back to 1778 when Long Islanders lived under an uneasy military occupation by the British commanders and troops. Route 25A, also known as Washington’s Spy Trail and formerly called The King’s Highway, rims picturesque and peaceful Long Island Sound, harbors and inlets. During the American Revolution, these hidden waterways were dangerous spots where the patriots operated boats to row intelligence to Connecticut and to General Washington that helped him win the war.  President Washington traveled the route on April 21 to 23, 1790, to thank the patriots and his spies.

During the Revolution, Joseph Brewster operated a tavern out of his home, Setauket’s The Brewster House, c. 1665, where he entertained British troops. Caleb Brewster, Joseph’s cousin, delivered spy messages between George Washington in Connecticut, and Abraham Woodhull in Setauket, pulling his rowboat into one of six different coves along the Setauket shore, including one located 150 feet from The Brewster House. Visit the house today which is owned and operated by the Ward Melville Heritage Organization, Stony Brook.

The Brewster House is just one highlight along the trail in Setauket, birthplace and home to the three friends, and an outpost to the British that they were determined to flush out. Other residents worked with them, including intelligence transmitter Anna Strong, and her husband Judge Selah Strong, who was arrested and incarcerated in the infamous British prison ship, Jersey.  Take a walking tour through the original settlement on Main Street, see the Village Green, and visit the churchyard cemetery where Abraham Woodhull and other famous Setauket residents were laid to rest.

In Huntington, colonial life during the 18th century can be experienced at the “working man’s home” of colonial weaver Job Sammis and his family that from 1775-1776 also served as the arsenal for the Suffolk County Militia which conducted regular drills on the adjacent Village Green prior to the British occupation of Long Island. During this occupation Nathan Hale volunteered to gather intelligence on the British forces in New York. He began his mission on the shores of Huntington Bay. He was later captured—it is unclear where, perhaps in Huntington or perhaps closer to the city—and hanged in New York City. The Nathan Hale Monument honors his sacrifice and is located on Route 25A, Huntington’s Main St., next to the Sailors & Soldiers Museum.

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