CYOA 2025 in review: Reflections on a memorable year

CYOA's 2025 in review © Stephen Cloutier

The 2025 CYOA season reinforced what many classic yacht enthusiasts already know: that these boats are far more than artifacts—they remain vibrant testimony to maritime history and formidable competitors in storied regattas. From Maine's rugged peninsulas to the historic harbors of Southern New England; and from friendly dockside dinners to fierce competition on the water, the CYOA community showed passion, perseverance, and a deep commitment to preserving and furthering the transitions of classic yachting.

Here is a brief recap of 2025:

A Grand Season Keeps the Summer Exciting

Before sailing in New England began for the year, the reach of classic sailing extended beyond New England: the CYOA's rating system, the Classic Rating Formula (CRF), was fully adopted by Antigua Classic Yacht Regatta as its uniform rating system. Among the participants was CYOA member yacht Juno, which took second place in the schooner division, and the 72-foot 1936 Herreshoff clipper Ticonderoga. Organizers praised CRF as an affordable, fair, and user-friendly alternative to traditional rating systems.

The 2025 season got off to a spectacular start in late June with the NYYC Tiedemann Classics Regatta in Newport, RI. This event—the first in the Classic Yacht Challenge Series (CYCS)—brought together some of the most beautiful classic yachts in the region for a weekend of racing and social camaraderie. As mid-summer rolled in, the Classic Yacht Challenge Series moved through a long slate of regattas spanning Maine, Massachusetts, and the southern New England coast.

The 2025 CYCS concluded in September—rounding out a season that spanned 14 regattas, from Down East Maine to the New York suburbs. In total, 262 classic yachts competed throughout the season; 17 qualified for the overall series by racing in at least five events.

The top honors went to some of the most storied names in classic yachting: the 1938 S&S yawl Black Watch achieved a perfect 500-point score to win the Vintage division overall. Close behind were the centennial-era 1925 Herreshoff R-Boat Gamecock and the 1936 NY 32 Gentian. In other divisions: the 12-Meter American Eagle took the Classic title, the newly built Brooklin Boat Yard sloop Jax won Contemporary, and the Herreshoff Narwhal—the only boat to qualify from the Modern Classic fleet—prevailed there. The spirited homebuilt daysailer Ponyo scored perfectly to capture the Spirit of Tradition class. Full results can be found on the CYOA website.

Offshore and Transatlantic Ambitions

2025 wasn't only about local regattas—some CYOA members took on daring offshore challenges too. One of the standout stories came from the Marblehead to Halifax Ocean Race (MHOR), one of the world's oldest offshore races. Under strong 15-18 knot winds, classic yachts posted impressive performances: Art Santry's JV66 Temptation won overall in record time (just over 45 hours), while the 1936 Herreshoff ketch Ticonderoga won her PHRF division, and the 1938 yawl Black Watch placed second in her ORR division—just 34 seconds behind first place.

But perhaps the boldest undertaking of the year was the participation of the classic 12-meter sloop Hound in the Transatlantic Race 2025. Hound, with a new keel, updated rigging, rudder, and fresh paint, set sail from Newport to Cowes, England on June 18. For owner Dan Litchfield and his crew, many of whom had logged multiple 600-mile races together, it was both a well-prepared adventure and a tribute to the boat's storied past. "We view these classic regattas as excellent competition," Litchfield said, underscoring how the CYCS circuit helped sharpen the boat's performance ahead of the ocean crossing.

Remembering Jesse Terry

Amongst the revelry of the summer season, CYOA lost a titan of the yachting world with the passing of Jesse Terry. Terry was a friend to all in our community and was known for his passion for classic sailing. A former CYOA board member, Terry consistently pushed our organization and community to be the best it could be.

Terry was honored at the annual CYCS award ceremony as the inaugural Abigail Trophy was awarded to Black Watch for sailing in the most CYCS events of any member of the fleet this season. The trophy is named for Terry's 1956 Alden Ketch, the beloved and famous Abigail, and a heartfelt tribute to him was delivered by his friend and crewmate Ben Ellcome.

Forging Ahead

Another stunning season of classic yachting is in store for 2026! Improvements to CRF, expanded membership, and the trademark slate of can't-miss regattas are set to make CYOA the club that everyone will want to join in the new year.

Thank you to our partners and members who made CYOA's 2025 one for the history books!

As always, stay tuned to the CYOA website for updates in the coming months.

Happy Holidays and Happy New Year from CYOA!