On Saturday, Sept. 13, a day of light and variable winds, the 18-foot Marshall catboat Rosa Parks, driven by Jeffrey Craig, won the gaff class at the 37th Pat West Gaff Rig & Schooner Race in Vineyard Haven.

“We just had a perfect day,” Mr. Craig said after the race. “I don’t think it could ever happen again.”

Rosa Parks was among the smallest boats on the race course. Aside from five well-handled schooners, she finished in front of every boat that registered. She beat almost 20, bigger boats to the finish line.

“The first three boats were catboats under 26 feet,” said Scott DiBiaso, Juno skipper and race co-organizer. “Conditions had a pretty strong influence on that.”

Mr. Craig’s experienced crew consisted of his daughter Seneca Craig and Dave Grubba, who had cleaned the boat’s bottom that morning.

Rosa Parks leads the way.

Mark Lennihan

Rosa Parks leads the way.

Mark Lennihan

“We won by 40 seconds. That’s nothing,” Mr. Craig said. “And we only won because we were totally vigilant. For two-and-a-half hours the only thing our crew talked about was our tactics. Not even once did any of the three of us not have our heads in the race.”

Most of the time Rosa Parks lives by herself, in a corner of Vineyard Haven Harbor, in front of the drawbridge. Many years Mr. Craig doesn’t take her in the race. But when he saw the forecast on race morning, he recognized Rosa’s chance.

“Rosa is light,” he said. “She doesn’t have a motor. It’s a lot of drive — one, big sail. But if we hadn’t been on it the whole race, we wouldn’t have had a chance.’

Not having a motor is another reason Mr. Craig and his crew are so good at sailing the boat in suboptimal conditions.

“Most of the reason we won, it’s been 26 years of trying to get home in light and variable shit,” he said.

“When you’re barely moving, that’s when you really have to pay attention to the boat,” Seneca said. Recognizing her Dad’s abilities, she added, “He’s spent so much time out there by himself.”

Until after World War II catboats were the workhorses of the Island’s local waters. It was a catboat that took people and goods every day from New Bedford to Aquinnah, and catboats that people used to fish for quarries as different as scallops and swordfish.

The Pat West Gaff Rig & Schooner Race is limited to boats with gaff rigs, an extra stick at the top of the sail that adds a fourth side to the currently fashionable triangle. Near the middle of the 20th century, it was still the most common way to rig a sailboat. It honors Commodore Pat West, a local man who had a deep love of sailing and being on the water.

Mr. Craig sailed with Pat West aboard Erda, his 23-foot Friendship Sloop in Mr. West’s last gaff-rig race, sometime in the early ‘90s.

“We got back after dark,” Mr. Craig recalled. “His wife Isabelle was waiting at the dock for us. He was 93 years old.”

In his 20s and working at the boatyard in Vineyard Haven, Mr. Craig first befriended Pat West when he and another gaff-rig sailor, Mr. Craig’s lifelong friend Paul Curran, modified their Marconi sloop, Trout Fishing in America, in order to compete in the next day’s race. They recut a castoff sail from a Vineyard 15 to turn their boat into a Bahamian headboard gaffer.

“Pat was very dear and encouraging,” Mr. Craig said.

Rosa Parks is not the first catboat Mr. Craig sailed in Vineyard Haven. In 1965, at 10 months old, his mother and father cruised in on a 23-foot Barnegat catboat that they sailed with all six of their kids. The four older boys had a tent they would set up on the beach next to Owen Park. Baby Jeff went in a hammock underneath the deck.

“This is back when they had courtesy moorings in Vineyard Haven Harbor,” he said.

Unlike most sailors, the Craig family continues to train on Rosa Parks year round.

“I’ve done more sailing in some Februaries than every June of my life,” Mr. Craig said.

He and his daughter are contractors and work in June is endless.