As Hugh Weisman prepared for the very first Chilmark Road Race in the summer of 1978, he wasn’t expecting much. The idea was inspired by the half a dozen or so children at the Chilmark Community Center he’d been running with all summer and he thought they would all enjoy the competition. Maybe 100 people would turn out, if that, he thought.

Instead, nearly 200 runners participated that year. Overwhelmed, Mr. Weisman and his team scrambled to shuttle all 180 runners by car, dropping them off at the starting point on Middle Road and wishing them well for their five-kilometer race to the town hall.

“And then it just got bigger and bigger,” said Mr. Weisman.

This year’s race, the 49th since its inaugural summer, sold out just a few hours after registration opened on July 1 (usually it takes a few days). The top limit, as per town rules, is 1,600 runners each year.

At the starting line in 2025. — Ray Ewing

This year’s race takes place Saturday, August 8, with a 10:30 a.m. start time.

“It’s become a kind of summer icon for many people,” said Mr. Weisman. “People arrange their vacations around it.”

Reflecting on the race’s growth from a grassroots running effort to a beloved summer event, Mr. Weisman said a combination of competition and community is what makes the Chilmark Road Race special. The event is well organized and hosts a plethora of talented participants.

“At the same time, it’s Chilmark,” Mr. Weisman said. “People see their friends.”

Being among familiar faces also takes some of the pressure off, he added. Even if the race gets delayed or the buses run off schedule, people are just happy to engage in some friendly competition.

Preparation for the race started back in June, Mr. Weisman said, when the team began updating the website and designing merchandise for the summer. In July, they dealt with logistics, getting permission from the town and state highway department and coordinating with the police, charter buses and trash pick-up teams.

In the days leading up to the race, organizers will trek along the five-kilometer route, painting mile markers on the road.

After three months of planning, Mr. Weisman said he’s looking forward to the moment the race ends, when a last, celebratory burst of energy washes over the exhausted runners.

“It’s kind of a party atmosphere,” he said. “At noon, when it’s done and no one’s gotten hurt and everybody’s happy — I can relax, and I can go get a slice of pizza at the Chilmark Store and let out a breath.”