Port Jefferson launches 250th anniversary with Revolutionary War whaleboat ceremony

Hundreds gathered at Harborfront Park in Port Jefferson for the ceremonial landing of The Caleb Brewster, a full-scale Revolutionary War whaleboat that became the centerpiece of the village’s 250th anniversary launch. The event turned the waterfront into a working history lesson, with colonial music, children’s games, reenactors and a landing demonstration that tied Port Jefferson’s identity to the intelligence network that once moved through Long Island Sound.

The vessel is the product of the Whaleboat 1776 Project, which LISEC said began in the fall of 2022 after the Village of Port Jefferson town historian approached Bayles Boat Shop with the idea of building a replica armed whaleboat. Built from historical plans by naval architect William A. Baker, the boat was crafted with traditional lapstrake methods and period-appropriate materials. Organizers said the project was completed in time for America’s 250th anniversary celebrations, more than three years after the first discussion.

Brookhaven Town Clerk Kevin LaValle said the event drew hundreds of attendees, underscoring how much interest the village can generate when its Revolutionary War history is put on display instead of left in the archives. John Janicek said the project took three and a half years and relied on more than 25 regular volunteers, with the final push coming in the last two months. The boat’s arrival marked not just a ceremonial finish line, but the public debut of a teaching tool intended to keep the Culper Spy Ring story visible on the waterfront.

The day’s program moved from the atmosphere of a colonial fair into more formal remarks from historian Mark Sternberg, Village Historian Chris Ryon and Mayor Lauren Sheprow. The Huntington Militia fired a cannon, a musket demonstration followed, and the whaleboat answered from offshore, turning the harbor into part theater and part history lesson. Organizers said Caleb Brewster, one of Benjamin Tallmadge’s informants in George Washington’s Culper Spy Ring, used his knowledge of Long Island Sound to ferry intelligence, and that the replica may later be displayed near the Drowned Meadow Cottage Museum. The village thanked the Robert D.L. Gardiner Foundation, Suffolk County Executive Edward Romaine’s office, LISEC, Bayles Boat Shop, the Greater Port Jefferson Chamber of Commerce, the Port Jefferson Conservancy, the Port Jefferson Historical Society and the Port Jefferson Arts Council for helping bring the project to the water.