60 boats set to take on Boothbay Harbor Yacht Club Regatta after thrilling Vineyard Cup
by Classic Yacht Owners Association 16 Jul 09:20 PDT
July 18-19, 2026
Vineyard Cup © Sail Martha’s Vineyard
With two regattas now complete, the 2026 Classic Yacht Challenge Series is beginning to take shape. And with a regatta on the schedule every weekend for the rest of the summer, the competition is only expected to intensify.
Last weekend, Martha's Vineyard came alive with the Parade of Sail and the 2026 Vineyard Cup Regatta. Nearly half of the 26-boat fleet consisted of CYOA members, who enjoyed near-perfect conditions throughout the weekend of racing.
While the leaderboard is starting to come into focus, it's still too early for official standings. To qualify for the Classic Yacht Challenge Series, boats must compete in at least five races across a minimum of three regattas, including one event outside their home district.
Among the standout performances at the Vineyard Cup were Spirit, Lars and Peter Forsberg's Alden schooner; Black Watch, helmed by Trevor Fetter; and Ben Sperry's NY32 Gentian in the Vintage Division. In the Classics Division, Mah Jong returned to competition with Alex Goldhill at the helm, joined by Scott DiBiaso's Nat Benjamin-designed Juno.
Complete Vineyard Cup results are available on YachtScoring, while preliminary CYCS standings can be found on the results page at classicyachts.org.
"Saturday featured the annual Vineyard Cup Pursuit Race, with a 14.8-mile course heading west toward Tarpaulin Cove before returning to Vineyard Haven," said SailMV's Andrew Nutton. "Sailors enjoyed an outstanding weekend of racing, which concluded with the prize-giving ceremony at the best party of the year—the Beach Party at the Sail MV Boathouse."
The fleet now heads north to Maine for the next chapter of the series. Racing continues this weekend at the Boothbay Harbor Yacht Club Regatta and Shipyard Cup Classics Challenge, where an impressive fleet of 62 yachts is expected to compete on July 18-19 in navigator races around Boothbay.
When this weekend concludes, all three CYCS regions will have hosted at least one event this season. As the schedule progresses, competitors will continue building toward qualification by racing across multiple regattas and venturing beyond their home districts.
Of course, Boothbay is about more than great racing. The regatta is equally well known for its outstanding shoreside hospitality, highlighted by the Saturday evening Dock Party featuring fresh Maine seafood, cold beverages, and plenty of post-race storytelling.
Now that the 2026 CYCS is in full swing, stay tuned to the CYOA Facebook, Instagram, and website for updates and results. Good luck to all competitors this weekend!