Classic Yachts Challenge Series

The organizing authority (OA) for the Classic Yachts Challenge Series (CYCS) is the Classic Yacht Owners Association (CYOA) in cooperation with the Organizing Authorities of the participating Series Events.

Vineyard Cup

Vineyard Haven, MA

New for 2024! Vineyard Cup has been added to the Classic Yacht Challenge Series!   Kicks off BIG BOAT RACING ON THE VINEYARD and is held on the waters of […]

Camden Classics Cup

Camden, ME

The must-not-miss event of the season with two days of racing around Penobscot Bay and amazing social events onshore hosted by Lyman Morse.

Camden to Brooklin Race

Castine Yacht Club

The second of the three distance races held in a weekend sends the fleet from Camden to Brooklin ahead of ERR.

Eggemoggin Reach Regatta

Brooklin, ME

The infamous wooden boat race is the largest of the season and sends the fleet west to Castine from Brooklin.

Nantucket Regatta

Nantucket, MA

Leading into the Opera House Cup, this Friday/Saturday event features buoy and distance racing.

Opera House Cup

Nantucket, MA

This event in its 52nd year the season highlight for this region. The pursuit race is followed by a parade and biggest social of the year.

Herreshoff Classic Yacht Regatta

Marblehead, MA

Featuring feeder races to and from Newport, the regatta takes place on Saturday followed by awards at the Herreshoff Marine Museum.

CYOA Annual Meeting and Awards

The Sailing Museum

Please Save the Date for the CYOA Annual Meeting and the CYCS Awards to be held in Newport, RI at The Sailing Museum.

Thanks to our Diamond and Gold Partners

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


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

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