When Charles Shipway watched the United States hockey team beat the Soviet Union during the 1980 Olympics, he knew he wanted to be an Olympian. But he had one problem: the other boys on his hockey team were starting to outgrow him.

“Everyone around me got big in hockey and I stayed small,” said Mr. Shipway, who grew up as a summer Chilmark resident before moving to the Island full-time in 1993.

He didn’t let his stature get in the way, though, eventually competing in the 1992 Olympics in Barcelona. But instead of being on skates it was in a catamaran, as part of the U.S. Virgin Islands sailing team.

On a window-side table at the Black Dog Tavern last week, Mr. Shipway displayed two discs. The first one was black, a memento puck from the 1980 Olympics, and the second one shimmered in metallic gray, with an inscription OLYMPIADA BARCELONA 1992.

“It was an honor and a privilege to be around all these people from around the world,” he said of the experience. “I would sit with so many different, interesting people, just flabbergasted.”

Mr. Shipway’s sailing journey began at a much-humbler venue, the long-running Menemsha Pond Races, and on a much smaller craft, the single-person Sunfish class sailboat.

In the past few years, Mr. Shipway has returned to his roots, competing in Sunfish tournaments again, but this time on a much bigger stage. In 2022, he finished 11th at the United States Masters Sunfish championship in Clearwater, Fla. This December he raced in the Sunfish World Championships in Miami and placed 54th out of 100 boats at the starting line.

But even while sailing in the middle of the pack, Mr. Shipway said his return to Sunfish racing has been invigorating.

“I was amazed, I’m way back, but there’s this beautiful sight in front of me,” he said, of falling behind on one of the races and surveying the competitors. “Even from back here, it’s not so bad.”

Mr. Shipway started sailing as a toddler with his father. By the time he turned 13, he had saved enough money from his summer job at the Chilmark Store to purchase his own Sunfish.

“For a kid who’s in too big of a boat for him to hold down, it’s pretty exciting,” he said. “You can break a mast and capsize and pitchpole.”

The racing course at Menemsha Pond was also the perfect place to begin, he said, getting a chance to compete against experts and beginners in a variety of sail conditions.

“It’s been a place for people from all walks of life, summer and winter to get together and go around in circles and have a good time,” he said of the races, a tradition dating back to the founding of the Menemsha Yacht Club in 1932.

When Mr. Shipway was growing up, the races were run by Arthur Railton, Island historian and longtime editor of the Dukes County Intelligencer.

“He cheered for the people who came in last,” Mr. Shipway said. “He did his best to make it inclusive.”

That inclusive leadership style was part of what made Mr. Shipway fall in love with the sport and the Menemsha sailing community.

“Traditionally in racing you go upwind and downwind, but we did things differently,” he said. “We do all the different points of sail, it’s a tour of the pond.”

While still a teenager, Mr. Shipway took over the leadership of the Chilmark Community Center’s sailing program.

“I kind of built it into something where, on nice sunny days, the center would be empty and everyone would be back on the water,” he said.

At age 31, he took over for Mr. Railton, who retired in 1999, running the Menemsha Pond races. He continued to do that for seven consecutive summers.

His Olympic journey began when he was still leading the Chilmark Community Center program. In 1988, he left college and moved to St. Thomas in the U.S. Virgin Islands for more time on the water. He spent his winters there, working construction and delivering sailboats to other islands such as Antigua, and returning to Chilmark in the summer.

In 1991 he saw an ad in the St. Thomas classifieds for a catamaran crew member. “I was the only one to answer the ad,” he said.

Though the pool vying for the U.S. Virgin Islands was small, the competition was tough, with Mr. Shipway’s team squeaking into the lead among qualifiers by three-tenths of a point.

Barcelona in 1992 turned out to be his only Olympics, though Mr. Shipway went on two more Olympic campaigns for the American team, trying to qualify for the Atlanta games in 1996 and Sidney in 2000.

But despite his globe-spanning waterfront career, Mr. Shipway’s heart remains at Menemsha Pond, where he has made an indelible mark on the up-Island sailing community.

The leadership role at the Chilmark Community Center, he said, has been a beacon for skilled, up-Island sailors. Sydney Karnovsky, who placed fifth in the 2022 women’s Sunfish World championship in Italy and second in the United States Pan-American Games trials in 2023, has also headed up the program, before rising star Kylie Craig recently took up the mantle. Both were Mr. Shipway’s pupils.

“It’s a generational thing, but it’s not by blood, it’s by community,” Mr. Shipway said.

And although times have changed, the traditions remain as they did in Arthur Railton’s time.

“We wait for the last person to finish,” Mr. Shipway said. “Just showing up and finishing, it takes a lot to get to that point.”