The Northeast sailing season kicks off in about three months and the CYOA’s Classic Yacht Challenge Series (CYCS) will be here before you know it! To continue our regatta spotlight series, we’re heading to the Islands of Massachusetts, home to Martha’s Vineyard’s Vineyard Cup.

To tell us more about these exciting events, CYOA caught up with Andrew Nutton of the Vineyard Cup:

CYOA: What is the history and tradition behind this regatta, and how does it influence the experience for participants?

Andrew Nutton: The Vineyard Cup was started to provide Vineyard Haven and the island as a whole with a large boat regatta in the summer. The other aim was to make the event a fundraiser for Sail Martha’s Vineyard to support its ongoing efforts to perpetuate and support the island’s maritime history and culture.

CYOA: What sets the fleet of classic yachts at your regatta apart from other similar events? Are there specific types of yachts or notable vessels that regularly participate?

AN: We offer scoring for all 5 of the recognized CYOA fleets. We see a large amount of Alerions, Cat boats, and Hereshofft 12.5s along with a whole array of different PHRFf spinnaker and no spinnaker vessels.

CYOA: What is special at your event to celebrate the classic yacht racing community during the event?

AN: The Vineyard Cup has always enjoyed a very healthy classics fleet. We offer classic fleet starts, with each individual CYOA fleet being recognized with a 1st place trophy.

CYOA: What aspects of your regatta make it a must-attend event for sailors and enthusiasts—whether it’s the location, race format, social atmosphere, or something else?

AN: The Vineyard Cup is the only major regatta on the island that runs out of Vineyard Haven and can access all areas of Vineyard Sound. This event is a key fundraiser for Sail MV, raising both funds and awareness for all the programs we offer to the sailing community of Martha's Vineyard. We also host the best beach party of the sailing season at the Sail MV boathouse, featuring fantastic food, drinks, music, and RC boat racing, all set against one of the best sunsets on the island. Additionally, we hold our annual seafood buffet and auction on the evening before the regatta starts. This is the only event held on the waterfront in Vineyard Haven and offers an evening full of food, drinks, music, and unique auction items, all in support of raising funds for Sail MV.

CYOA: How does your regatta engage the wider community, and are there unique activities or events that connect spectators and non-sailors with the world of classic yachts?

AN: The Vineyard Cup is advertised thoroughly through all our social media outlets as well as the involvement of our print and radio media partners. We run a Parade of Sails on the Saturday morning of each event, which sees many non-sailors watching the fleet as they prepare for a day's racing. We make sure the start and finish lines for each day’s racing are close to shore, allowing for our community as a whole to enjoy the view of our competitors beginning or finishing a day's racing.