Roe was the owner of a tavern in East Setauket. "Roe's Tavern" is an extant structure where George Washington stayed overnight during his 1790 tour of Long Island.
Culper ring
Background
In December 1778, General George Washington's chief of intelligence—and Culper Ring spymaster Major Benjamin Tallmadge—recruited Jonas Hawkins as a clandestine courier to bring messages to Setuaket from New York City, where the group's leader, Abraham Woodhull was gathering information. From there, the coded correspondence could be relatively easily forwarded to Tallmadge. At first, the ring employed just Hawkins in the role, but by early summer, Roe had joined the group as an alternate rider, who would take messages the between the group's two major centers of operation, Setauket, New York and New York City. At the time, both cities were occupied by the British.
Work as spy
Roe and Hawkins passed the messages from New York City to operative Caleb Brewster on Long Island. Brewster would take them across the Sound to Tallmadge at Fairfield, Connecticut. From there, Tallmadge forwarded the messages to Washington. Roe served the Culper spy ring as a courier by secretly relaying its messages beginning in early 1779. He claimed to be conducting business as a merchant in order to avoid suspicion and pass through the British check-points. Roe became the sole dispatch carrier for the ring after July 1779, when Tallmadge gave Roe–but not Hawkins–a code number in his code index. Hawkins increasing paranoia had led him to abandon the mission at that time.
In historical records
Because Roe traveled over 1000 miles on horseback performing his missions during the war, he has been called the "Paul Revere of Long Island." In 2015, a letter written by loyalist soldier Nehemiah Marks to Adjutant GeneralOliver De Lancey, head of British Army Intelligence following Major John Andre’s capture and execution, was uncovered. The document contained information that brothers Nathaniel and Phillip Roe were part of the "Long Island spy network," but the allegations were neither investigated nor acted upon.
Later life
After the war, Roe continued to operate his tavern in Setauket. He became a captain in Lieutenant Colonel David Pierson's New York militia regiment in Suffolk County, New York, in 1787. He and his family settled the area which would become the town of Patchogue on Long Island's south shore in 1798. He opened an inn there, where for three decades he regaled his patrons with tales of his exploits during the war. Roe died in Suffolk County in 1830 at the age of 82; and was buried in the family graveyard. His body was eventually re-interred in the Cedar Grove Cemetery, in Patchogue, after the town was founded by a descendant.
