Eight Bells: Jesse Terry

Jesse Terry (1979–2025) — sailor, writer, and loyal friend to many in the classic yacht community — passed August 1 while preparing Abigail, his beloved 1956 Alden ketch, for a series of classic yacht races in Maine.

Jesse sailed out of Noank, CT, and lived in New York City with his wife Annie and their twins, Corby and Brakeley. His father, Michael Terry, with his discerning eye, was often by his side in the boatyard, lending wisdom during Abigail’s winter projects and taking the helm during family cruises with his grandchildren.

Above all, Jesse’s greatest love and devotion was to Annie, Corby, and Brakeley—along with the wide circle of family and friends who gave his life its deepest meaning and joy.

Jesse was a member of the New York Yacht Club (NYYC) and the Cruising Club of America (CCA). Within NYYC, he served on the Sailing Committee and as event chair for the Robert H. Tiedemann Regatta. In the CCA, he chaired the Next Watch Committee, mentoring the next generation of bluewater sailors.

He also served on the Board of the Classic Yacht Owners Association, where his steady presence and vision helped shape the Classic Yacht Challenge Series. In addition, Jesse was a founding board member of New London Community Boatworks, a nonprofit dedicated to youth development through boatbuilding and connection to the city’s maritime heritage.

On the water, Jesse’s life was as accomplished as it was passionate. He completed seven Bermuda Races, including the 2014 race as part of the crew of Blackwatch, which was awarded the Arthur B. Hanson Rescue Medal by US Sailing. He cruised from Fort Lauderdale to Newfoundland, and each summer raced in New England’s Classic Yacht Challenge Series from Greenwich, CT, to Penobscot Bay, ME—eventually making the podium in every port.

Among his proudest achievements was winning the 2018 Opera House Cup with his sister, Sarah Terry. Just days before his passing, he won the Vintage Division at the Camden Classic Cup, following a cruise from Halifax to Maine with lifelong friends from his prep school days. He also recently competed in the Marblehead to Halifax Race, continuing his lifelong pursuit of seamanship and camaraderie offshore.

What set Jesse apart was the way he intertwined friendship with seamanship. Abigail’s crew was a reflection of his journey—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 all found a place aboard. This spirit of welcome and camaraderie made Abigail the “fun boat” at the dock or in the mooring field.

Beyond racing and service, Jesse was a gifted writer, whose reflections captured the spirit of stewardship and joy that define classic yacht ownership. His words will continue to inspire all who share his love of wooden boats and the communities around them. A fitting measure of his impact came when 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.