5. Roe Tavern

Roe Tavern is a historic building that originally stood on Main Street from 1703 to 1936 and now stands on a private road about a mile away. The tavern was owned by Austin Roe, a member of the Culper Ring, a spy ring established in 1778 during British occupation of New York City.

Roe worked as an alternate rider with the Culper Ring, meaning he would take messages 55 miles from Setauket to the city. He has been considered by some as the “Paul Revere of Long Island” since he traveled over 1000 miles throughout his career. A plaque on Main Street at its original location notes that George Washington, who organized the Culper Ring, stayed at the inn on the night of April 22, 1790.