The 20th anniversary of the Martha’s Vineyard Challenge was golden. The Saturday sailing and paddling event raised $14,423 for Martha’s Vineyard Community Services. High winds and bright sunshine made the day perfect for windsurfers and a challenge for sailors and paddlers.

The 43 registered participants and their friends set a record in fundraising.

“We just had a perfect set of conditions,” said Nevin Sayre, 47, founder and leading participant in the event. A windsurfer, Mr. Sayre was able to complete a round-the-Island sail in 4 hours and 21 minutes. After completing his round-the-Island sail, he sped into Vineyard Haven outer harbor at the same moment that four larger sailboats crossed the start of their race.

The challenge is more expanded than in past years. Mr. Sayre said this year’s significance came in the form of enthusiasm in those who joined and the coinciding good weather.

“Last year we had a gale; it was blowing over 30 knots. In the last two years hurricanes threatened,” Mr. Sayre said. So, of course, this year was far better.

Of the 15 windsurfers who started the round-the-Island race, only two finished. Steve Besse of Vineyard Haven and Guilford, Conn. came in second, completing the race in five hours and 18 minutes. Both he and Mr. Sayre are longtime friends and windsurfing enthusiasts.

There would have been a third-place winner if the sea conditions off Wasque weren’t so bad.

Mr. Sayre said the counter-clockwise trip around the Vineyard was fine until the sailors got off Aquinnah and Squibnocket. “The wind in the morning started in the northwest. Most of the sailors did well going from West Chop to Gay Head. But off Squibnocket the windsurfers encountered an opposing current.

“When the wind shifted to northeast, it became a long sail to Edgartown,” Mr. Sayre said, because the sailors were beating not only the current but a stiff wind.

Tim Colon of Vineyard Haven got as far as Katama and was doing fine until he got to Wasque, where the current and the waves were just too rough.

Sailing safety is a big part of the round-the-Island race. Mr. Sayre said all the sailors had marine radios. There were checkpoints on the beaches all around the Island. There were also chase boats.

One of the great attributes of the annual 55-mile race, according to the founder, is the attention to safety. For any windsurfer considering sailing around the Island, there is no safer way to do it than from within the annual race.

Nine kayaks were tested in their race off West Chop. Malcolm Boyd, a local favorite, capsized in his kayak twice and was assisted by others.

Wilton Holmes, 59, of Durban, South Africa, was paddling in a 14-foot yellow fishing kayak called paddle ski in his home country. He ended up assisting Mr. Boyd in at least one flip. He capsized himself in his allegedly unsinkable boat.

“It was very choppy. There were a lot of short waves. Plus there were waves from passing ferries,” Mr. Holmes said.

But the best part of the race wasn’t just on the water. Mr. Holmes said he had an opportunity to meet other kayakers and share in the fellowship of like-minded thinking. “Even back home in South Africa there is such camaraderie,” he said.

Dr. Michael Jacobs went sailing in his 30-foot sloop Sakie. His colleague and sailing friend Dr. Richard Koehler worked aboard. “It was a great day for sailing in heavy weather conditions,” Dr. Jacobs said.

“You needed three hands, one on the tiller, one on the main sheet and one on the manual bilge pump,” he said. “The best part was we got a great soaking for four hours and at the same time made a contribution to Community Services.”

The participation of sailing boats is a new and bigger component to the challenge. Four sailboats raced. Dr. Jacob’s boat came in third. The fourth and last boat, Sandlerling, captained by Francie Desmone, had important crew aboard: Laura Hacker-Durbin and her husband Randy Durbin. Ms. Hacker-Durbin was a key organizer of the sailboat component of the day in racing.

“I like to think that we as members of the sailing community, can come together and support Community Services in our own way,” she said.

The entry fee was $100 for each of the sailboats, and participants were encouraged to go out and add sponsors. Sponsorships is a big part of how the challenge can be a big fundraising tool.

Fund-raising awards went to three people on Saturday. First place went to Mr. Sayre for raising $2,465. Second place went to Keith Gross, who raised $1,708. The top youth fund-raising award went to Jessilee Gross for raising $1,400.

Mr. Sayre said that Saturday’s event pushed the top when compared to all previous 19 events. In past years the event has typically raised just under $10,000.

“This one pushed us over $200,000,” he said.

So many of the participants in The Challenge return year after year.

“This is more than a race,” Mr. Sayre said. “Everyone has their own personal challenge, whether it is going around the Island for the first time or doing it for the sixth or seventh time. It could also be about raising more money for Community Services than you’ve ever raised before.”

Ms. Hacker-Durbin said the day’s success wasn’t just in sailors or paddlers but in the infrastructure of those ashore and on the water giving support. She said accolades should go to the Vineyard Haven Yacht Club crew for providing the committee boat Vigilant to officiate the start and end of races.

Mr. Sayre said the challenge began 20 years ago as a windsurfing event.

“It really became the same crowd of people gathering year after year,” he said. “We thought to grow the event, we had to include non-motorized crafts.”

This year they got what they sought.

Kayaking Results:

Short course: 1, place, Chris Crovatto; 2, Veronika VandeGeer; 3, Eli Hanschka and Chase Lewis.

Long course: 1, Dana Gaines; 2, Whit Hanschka; 3, Tyler Stapleton. Master’s Course; 1, Lucy Myers; 2, Herb and Donna Foster.

Sailing Results:

Vineyard Challenge Heritage Fleet (Performance Handicap Racing Fleet): 1, Peter Howell in Gwyn Erye; 2, Hugh Martin on Moira Elizabeth; 3, Michael Jacobs on Sakie; 4, Francie Desmone on Sanderling.

Windsurfing Results:

Vineyard Challenge Fleet, Around the Island (55 miles): Fifteen participants started; two completed: 1, Nevin Sayre, 4 hours, 21 minutes; 2, Steve Besse, 5 hours 18 minutes.

Vineyard Challenge Enduro Windsurfing (at State Beach): 1, Solvig Sayre; 2, Philippe Jordi; 3, Gary Harcourt; 4, Rasmus Sayre; 5, Elie Jordi.