The sailing world is grieving the loss of Jesse Terry, a devoted yachtsman, mentor, and lifelong advocate for maritime heritage whose impact on the community will be remembered for years to come. Jesse’s passing marks the end of a life defined by passion for the water, camaraderie, and service to both youth and fellow sailors.

A Life Dedicated to the Sea and Community
Jesse served on the Board of the Classic Yacht Owners Association, where his steady guidance and vision helped shape the Classic Yacht Challenge Series, one of New England’s premier sailing competitions. He was also a founding board member of New London Community Boatworks, a nonprofit organization focused on youth development through boatbuilding and fostering connections to the city’s rich maritime heritage. His work off the water reflected his dedication to nurturing the next generation of sailors and boat enthusiasts.

An Accomplished Sailor
Jesse’s life on the water was filled with remarkable achievements. He completed seven Bermuda Races, including the 2014 race aboard Blackwatch, a crew honored with the Arthur B. Hanson Rescue Medal by US Sailing. His cruising journeys took him from Fort Lauderdale to Newfoundland, and each summer he competed in the Classic Yacht Challenge Series across New England, earning a podium finish in every port.

Among his proudest accomplishments were victories alongside his sister, Sarah Terry, including winning the 2018 Opera House Cup. Just days before his passing, Jesse captured the Vintage Division at the Camden Classic Cup, following a cruise from Halifax to Maine with lifelong friends. He also recently competed in the Marblehead to Halifax Race, exemplifying his lifelong dedication to seamanship and fellowship offshore.

A Spirit of Friendship and Camaraderie
Jesse was known for intertwining friendship with seamanship. His crew aboard Abigail included dorm mates from the Frederick Gunn School, fraternity brothers from the University of Pennsylvania, colleagues from his New York City real estate career, and lifelong friends. This spirit of inclusivity made Abigail known as the “fun boat” at the dock and in the mooring field, leaving an indelible impression on everyone who sailed with him.

A Lasting Legacy
Beyond sailing, Jesse was a gifted writer, capturing the spirit of stewardship and joy inherent in classic yacht ownership. His reflections continue to inspire enthusiasts and maritime communities alike. In recognition of his enduring influence, he was posthumously awarded the Gwen Gaillard Spirit of the Race Trophy at the 2025 Opera House Cup, honoring the sailor or boat that best exemplifies the spirit of the event.

Jesse Terry’s life was a testament to passion, friendship, and service—both on and off the water. His contributions to sailing, mentorship, and maritime heritage will leave a lasting legacy in the hearts of those who knew him and in the broader sailing community.