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.”
WHAT TO KNOW
- Caleb Brewster was a whaleboat captain and a key member of the Culper Spy Ring that helped George Washington win the Revolutionary War by ferrying secret information from locations including Port Jefferson across Long Island Sound.
- 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 recreating the 24-foot-long wooden vessel in a boathouse overlooking Port Jefferson Harbor that Brewster and his comrades used to enter to conduct raids and secret missions.
“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.
Two years later, Brewster offered to provide intelligence reports that would be conveyed to Washington’s head of military intelligence, Benjamin Tallmadge, in Connecticut, according to the book “George Washington’s Long Island Spy Ring” by former Newsday reporter Bill Bleyer. Washington needed to know details such as the locations and sizes of British troops and vessels.
Tallmadge grew up in Setauket and knew Brewster and many of the other people who became Culper spies.
Robert Townsend was a merchant from Oyster Bay whose spy ring alias was Samuel Culper Jr. He worked in British-controlled New York City, where he gathered intelligence on the redcoats, Sternberg said.
He passed it to couriers including Austin Roe, a tavern keeper who took it by horseback 55 miles to his home area of Setauket. Some notes were written with invisible ink provided by Washington. Others used a code in which numbers were substituted for common words, places and names. The code for Brewster was 725.
Roe would give the information to one of the ring’s main organizers, farmer Abraham Woodhull, alias Samuel Culper Sr. Woodhull then passed the information to Brewster, who, with a small flotilla of whale boats, would evade armed British boats at night and row for hours across the Sound from patriot-controlled Connecticut and back, Sternberg said.
In Connecticut, the information was carried by horseback to Tallmadge and then to Washington at his headquarters north of Manhattan or in New Jersey.
The ring notched some major accomplishments. In July 1780, it prevented a British fleet from sailing for Newport, Rhode Island, which would have stymied plans by the French to land 6,000 troops there who helped the patriots.
Kristen J. Nyitray, associate librarian at Stony Brook University, said Brewster’s role in the spy ring has been “underexamined” by historians. The university’s libraries are in possession of two letters authored by Washington relating to the ring.
“The significance of Caleb Brewster's role in the Culper Spy Ring cannot be overstated,” Nyitray said. “If not for Brewster's maritime prowess, courage, and tenacity, George Washington would not have obtained the information needed to inform his military actions.”
The replica project should help bring Brewster’s role “to the forefront,” she said.
As the boat emerges little by little, historians are uncovering more information about the spy ring — and dispelling some myths.
Sternberg said it is becoming clear that the ring was larger than previously known, and that Port Jefferson — where Brewster often landed — played a bigger role than was thought.
He has also helped confirm that one famous story — that spy ring member Anna Strong would hang handkerchiefs and petticoats on her clothesline in what today is called Strongs Neck to indicate to Woodhull that Brewster had arrived and where — is false.
Strong did not live there at the time, but rather on the other, eastern side of the Port Jefferson Harbor, in what today is called Belle Terre. It was also not true that she hung the clothes as a signal, because Brewster and his men would arrive under the cover of night to hide their activities, Sternberg said.
Sternberg “is really changing the story of the Culper Spy Ring,” Ryon said. “He has found a lot of things that people had no idea.”
Sternberg said there is more to come.
“We act here like we have a complete record. We don’t. We don’t know every single thing that the spy ring pulled out of New York City and provided to American generals,” he said. The research is “an ongoing journey.”