The Vineyard Cup attracted 106 boats on Saturday for a 13-mile race across Nantucket Sound and back. The sailboats crossed the start in four separate class starts around noon.

Sailboat prepares to pass buoy in Vineyard Haven outer harbor. — Mark Alan Lovewell

In the three days of racing that began on Friday and ended on Sunday, one of the newest boats on the waterfront did the best.

Nat Benjamin’s 50-foot schooner Charlotte, which was launched last September in Vineyard Haven, won Saturday in her class and won in Sunday’s ocean course race, which drew 85 boats. Not bad for a new boat in Vineyard sailing competition.

Sunday’s race followed a pursuit format, with a different start for every boat. The slowest sailboat started first and the fastest started last so that with proper winds, everyone was expected to finish at the same time. They almost did.

Windsurfers speed through waves outside harbor. — Mark Alan Lovewell

“It was the coolest thing seeing 20 boats all coming towards the finish at the same time,” said Phil Hale, a sailor in the race, a director of Sail Martha’s Vineyard and an owner of Martha’s Vineyard Shipyard.

In other Cup events, pilot gigs raced off Eastville Beach on Saturday morning. Rowers came from as faraway as Gloucester and Hull to compete in the gigs. Windsurfers participated in the East Coast Junior Olympic Windsurfing Championships.

For much of the weekend, sailboats, rowboats and windsurfers sped across the harbor in Cup competition.

On Friday, Saturday and Sunday nights, festivities were held under the tent, on the dock and on the beach at Owen Park. Sailors and their friends gathered to share in the fellowship of the weekend events. Attendance in each of the events was estimated at more than 300.