During the American Revolution, the Brewster House functioned as both an inn and tavern. At least two British soldiers were quartered here, while indentured and enslaved individuals continued to live on the property.
The tavern was a vital hub of information exchange.
Joseph Brewster II had deep family and social ties with members of the Culper Spy Ring, the Revolutionary War intelligence network operating on Long Island.
Through kinship and marriage, the Brewsters were connected to Anna Smith Strong, who is believed to have played a key role in signaling messages to George Washington’s agents.
Joseph II’s second cousin was whaleboat captain Caleb Brewster. A key member of the Culper Spy Ring, Caleb was responsible for transporting critical intelligence gathered in Manhattan across the Long Island Sound. He was a vital link in the chain of information to General Washington.
The cove directly behind the Brewster House, known as Setauket Harbor, was one of six locations where Caleb Brewster would quietly dock his whaleboat.