CYS Region Spotlights: Massachusetts

Photo: Bruce Durkee

Spring seems to finally have sprung in the Northeast! Just over one month remains until the first of the 2026 CYCS Regattas. Next up in our series of CYCS region spotlights is the Bay State. Four of the 14 regattas in the series take place off the coast of Massachusetts:

Dramatic coastlines and legendary waters in some of New England’s most popular summer destinations make these regattas some of the most popular in the series. The Vineyard Cup is a summer kickoff event as the second regatta of the season. The Corinthian Classic Yacht Regatta is a premier summer event in the sailing-obsessed town of Marblehead. The Nantucket Regatta and Opera House Cup go hand in hand, taking place on consecutive days and both part of Nantucket Race Week. More information on these regattas can be found on their spotlight pages linked above.

Registration for The Vineyard Cup and Corinthian Classic Yacht Regatta will be open soon, and is already open for Nantucket Race Week on their brand new website. The Opera House Cup will continue to use the popular new marks and alternate start and finish lines that were introduced and well received in 2025. The regatta hopes to grow its Invitational Division, which is open to non-wooden-hull boats that add spectacle to the fleet.

In the Massachusetts Division of the 2025 CYCS, Siren (Peter Cassidy) led the Vintage class with 271.43 points, followed by Gentian (Ben Sperry) at 263.33; Outlier (Harvey Jones) topped Contemporary with 300 points; and Juno (Scott DiBiaso) claimed Classic division with 280 points. Be on the look out this summer for these yachts to defend their titles!

All 2026 CYCS events are posted on CYOA’s event calendar with more information on each regatta. Summer will be here before we know it—start planning your 2026 CYCS campaign today!


Thanks to our Diamond and Gold Partners

Interested in becoming a partner of the CYOA? Join as a Partner online or contact us at info@classicyachts.org for details.

SPERRY SAILS




The Classic Yacht Owners Association is an exempt organization as described in Section 501(C) (3) of the Internal Revenue Code. Donations and membership fees are charitable contributions and tax-deductible. Employer Identification Number: 81-285925

© Copyright 2025. All Rights Reserved. Website by risingT, LLC.