Classic Yacht Challenge Series 2025 Wraps Up

A season of tight racing and timeless yachts concluded with top awards at the Indian Harbor Classic Yacht Regatta.
Classic Yacht Challenge Series
Black Watch (pictured), Ponyo, and a fleet of timeless yachts headlined the 2025 Classic Yacht Challenge Series wrap-up. Bruce Durkee/Courtesy CYOA

The 2025 Classic Yacht Challenge Series (CYCS) closed its season last weekend with the Indian Harbor Classic Yacht Regatta in Greenwich, Connecticut. Over the summer, the series drew 262 classic yachts to 14 events spanning Down East Maine to Long Island Sound, with 17 boats qualifying by competing in at least five regattas.

“This was a challenging season, but it was marked by tight competition, strong camaraderie, and a thorough commitment to classic yacht racing,” said Timmy Dittrich, chair of the Classic Yacht Owners Association. “On behalf of the Classic Yacht Owners Association, I want to extend a heartfelt congratulations to our winners, and plenty of gratitude to all the sailors who participated in this summer’s season.”

Top Honors Across Classes

In the Vintage class, the 1938 Sparkman & Stephens Black Watch secured a perfect 500-point score to take first place. Peter McClennen’s 1925 Herreshoff R-Boat Gamecock placed second with 490 points, followed by Ben Sperry’s 1936 NY 32 Gentian with 433 points. Paul Koch’s homebuilt daysailer Ponyo earned a perfect score in the Spirit of Tradition class. In the Classic division, American Eagle, an A. E. Luders Jr. 12 Meter owned by Alexander C. Valcic, claimed top honors. Øivind Lorentzen’s Brooklin Boat Yard–built Jax won the Contemporary class, and Steve Frary’s Herreshoff Narwhal led the Modern Classic fleet.

“Qualifying means dedicating the logistics and the time to get around New England,” Dittrich added. “We know this is not an easy feat to be stewards of these pieces of history and we appreciate all those regattas, owners, and sailors who travel to celebrate the classics all summer long.”

District Awards and Milestones

District awards recognize boats that sail at least three events in their home region. In Southern New England, McClennen’s Gamecock clinched the Vintage division, marking 100 years of the R-Boat on Narragansett Bay. Stephen Antaya won the Classic division aboard his 1959 Alden yawl Mariner, while William Hubbard’s 1969 Tina One Tonner Lively Lady topped the Modern Classic fleet.

The winners will be celebrated at the CYOA Annual Meeting and CYCS Awards Ceremony on October 24 at the Herreshoff Marine Museum in Bristol, Rhode Island. Members and sailors are invited to RSVP by October 14 on the CYOA website.

Looking Ahead to 2026

Despite light conditions in the season finale, the fleet delivered a memorable finish to the summer series. Full results from the Indian Harbor Classic Yacht Regatta and the complete CYCS standings are posted on the CYOA website.

The Classic Yacht Challenge Series will return next summer for another slate of events celebrating the enduring beauty and spirit of classic yacht racing.