Port Jefferson volunteers building replica of boat used by Revolutionary War spy who helped George Washington

Caleb Brewster was a key member of the Culper Spy Ring that helped George Washington win the Revolutionary War. A daring whaleboat captain, he ferried secret information from Port Jefferson and Setauket across Long Island Sound as part of a network that allowed Washington to outfox the British.

Now, the Village of Port Jefferson is constructing a replica of Brewster’s boat as the nation approaches the 250th anniversary of its Independence.

Volunteers are painstakingly recreating a 24-foot-long wooden vessel that Brewster and his comrades used for conducting raids and secret missions. The work is being done in a boathouse overlooking Port Jefferson Harbor. The replica will be displayed in parades and at museums, and for re-enactments on the water.

Mark Sternberg, an expert on the Culper Spy Ring at the Drowned Meadow Cottage Museum in Port Jefferson, called the boat project “awesome.”

“Caleb is such an integral part of the Revolutionary War, especially here on Long Island,” Sternberg said. “He was instrumental for the Culper Spy Ring, getting the intelligence to Washington. It wouldn’t have existed without him.”

Brewster, he added, was “a character. He was bold, he was brave, he was a bit reckless. He also liked to party. It’s hard not to love Caleb Brewster.”

The boat is being built at Bayles Boat Shop in Port Jefferson by two dozen volunteers — among them retired teachers, lawyers, engineers, scientists, school bus drivers and electricians. They started in September and expect to finish by fall 2024, said John Janicek, a retired aerospace engineer for Northrup Grumman.

The boat will include five oars, a sail and a swivel cannon like the one Brewster used. The whale boats were especially good for wartime because they were fast, light and quiet, and could outmaneuver large sailboats, said Chris Ryon, Port Jefferson's village historian.

The project is challenging, said Len Carolan, who heads the volunteers. Two other replicas were built in Huntington and Darien, Connecticut for the nation’s bicentennial in 1976, but now are in disrepair, he said. The Port Jefferson group tracked down the drawing plans those groups used for the boats in the archives at Massachusetts Institute of Technology in Boston.

Ryon called Brewster "a hero, a star" who escaped death multiple times; during a sea battle he was shot and nearly died.

The spy ring has gained national attention over the past decade through new books and an AMC series, “Turn: Washington’s Spies.”

The latest effort is a new film called “The Whaleboat War” that will focus on Brewster, the spy ring and the replica project. It is being produced by Port Jefferson native Michael Tessler, who hopes to release it in 2025.

"Our community has had a profound impact on the course of human events,” said Tessler, who is based in Los Angeles. “It is time for us to tell that story and to utilize some Hollywood magic to bring our hometown's extraordinary history to life.”

The cloak-and-dagger network, sometimes also called the Setauket Spy Ring, involved multiple residents like Brewster who, in some cases, risked their lives to help the patriots defeat the redcoats.

Washington had been working on an intelligence network since the disastrous Battle of Long Island in August 1776 when the British routed the patriots, who had to escape by night from Brooklyn across the East River to Manhattan. Brewster took part in the battle.