The boaters on the water were not the only winners Sunday at the 15th annual Martha's Vineyard Oar and Paddle Regatta.

It was the first time a pilot gig boat from Vineyard Voyagers participated. It was the first time for live music on the beach. And the nonprofit organization Friends of Sengekontacket will receive a check for more than $1,000, raised through registration fees.

The two-and-a-half-mile race was held off Joseph A. Sylvia State Beach. Sixty-five paddlers and rowers began in Sengekontacket Pond near the Little Bridge, also known as VFW Memorial Bridge. They then raced down to the Big Bridge (American Legion Memorial Bridge), went under it and into Nantucket Sound, and then headed back to the Little Bridge. It was a reversal of the usual course and took advantage of the current flowing out of the pond, under the Big Bridge.

Dana Gaines, 48, of Edgartown was the first kayaker across the finish; he completed the course in 23 minutes and 52 seconds. John Moore, 51, of West Tisbury, was two minutes behind him (25:53). It was appropriate for the two men to take the top positions - they founded the regatta.

Later, Mr. Moore said of his friend: "Dana always wins. Not only does he have the fastest boat, with racing wing paddles, he is the only one in his division. Dana could win in a six-foot bathtub."

Percy Burt, 45, of Vineyard Haven, was another top competitor. He won in his category of plastic kayaks 16 feet long to 18 feet long. Mr. Burt, a rowing enthusiast, is a frequent winner.

The regatta was for paddlers of all ages. Five-year-old Jack Hayes of Edgartown was the youngest competitor. The eldest, Herb Foster, 77, of Edgartown, was out for his first day of kayaking all summer. Mr. Foster is a retired teacher from New York city and a former president of the Martha's Vineyard Hebrew Center.

"The Sound side was rough," Mr. Foster said afterward from under the brim of a white floppy hat. Indeed, winds were kicking up one-foot seas off the beach.

The rocking trip to the finish put four-year-old Caroline Keller to sleep. She was in the event's smallest kayak, not officially entered. Her little boat was towed by her grandfather, Pat Loftus, 62, of Quarryville, Pa.

"We plan our visit to the Vineyard around the regatta," Mr. Loftus said. "It is a highlight of our summer."

There were two other boats for the Loftus family. Fran Loftus and Tracy Keller, Caroline's mother, were each in boats. All family members wore life jackets; even young Caroline was dressed in a wet suit and wore an offshore lifejacket with a big red whistle.

The 32-foot pilot gig Grace was an event unto itself with a crew of six and a coxswain.

The vessel completed the race in 27:03 minutes. Coxswain Malcom Boyd of Vineyard Haven said the boat had been rowed from Vineyard Haven earlier in the morning by another crew. Mr. Boyd is the vice president of Vineyard Voyagers and a cofounder. For the crew aboard, the day brought out another level of fellowship. Sterling Wall, 58, of Chilmark, and his son Sterling, 17, of Marshfield rowed next to each other in the boat.

"What is nice about the boat is that it brings all kinds of people together," Mr. Boyd said.

"We have a hard time keeping up with these older gentlemen," said Dave Murphy, 34, of Vineyard Haven, a gig rower. Mr. Murphy is a member of the Dukes County sheriff's department.

Going under the bridge was one of the biggest challenges for the pilot gig. Mr. Boyd explained that each oar is 14 feet long, and the beam of the vessel is five feet. "That means we have a breadth of 25 feet," Mr. Boyd said. So the six-man crew pointed their oars toward the stern and relied on the current and inertia to make it to the other side.

Ed Lee Oliver, 60, of Edgartown had a noisy time heading under the bridge. He rode the only kayak with a plastic mast and sign pennants. Fortunately, the mast flexed as his boat went underneath. The tip of the mast hit each bridge rafter with a clap. The displayed sign flags spelled out: "MVOP15."

A shoreside attraction included Gian Carlo Buscaglia, a Latin music singer and guitar player. Mr. Buscaglia brought his own sound system and played Latin American dance music and sang.

Much of the day's work was handled by a small army of volunteers. Friends of Sengekontacket president Hap Hamill and his wife, April, collected the entry fees.

Mac Reed, former president of the nonprofit organization and a member of the board of directors, said the regatta is the single public event that promotes the Friends of Sengekontacket, which is committed to protecting the water quality of the pond.

Last year the regatta donated $500 to the group; this year organizers anticipate that the check will be more than twice that amount.

"The people involved in putting this regatta together are great; we are grateful," Mr. Reed said.