Sheridan Wilbur, 17, of North Smithfield, R.I., woke up at 5:20 on the morning of the 37th annual Chilmark Road Race. She piled into a car with her family and they drove to Woods Hole. There was a bus from the parking lot, the boat ride over, a bus to Chilmark and finally a bus to the starting line of the race.

After that Sheridan needed only her feet, crossing the finish line in a brisk 18:24.55 to earn the top women’s time in the race, placing 13tth overall. Though the rising high school senior has taken first place in her age group before in her four years of running the route, she’d never won the whole thing. But on Saturday morning, she finished with both a victory and a personal best.

“I was running with another woman for the first two miles,” she said after the win. “I started to break away from her then.” The famous hills of the topographically challenging race start to appear at about that point, but as Sheridan said, “As soon as you get to the top, you have the ocean view and you think, oh, the finish is close.

“It was cool just to break the tape.”

David Melly, 21, of Newton, knows exactly what it’s like to break the tape, too. The winner of the 2011 race, Mr. Melly blazed to a sub-16-minute finish (15:43.31) to take first place once again. A rising senior at Cornell University, where he competes on the cross country and track squads, Mr. Melly said his familiarity with the course helped secure the win.

“In this race I was pretty much just chilling in second place until the last mile,” he said. “The hills become your friend. You can use them to your advantage.” In the final stretch, everyone has the same advantage: the packs of cheering spectators on both sides of the road, forming a veritable tunnel of support.

“That’s so much fun,” Mr. Melly said. “More than anything else, I think that’s why I keep doing this. It’s the best finish. It’s very, very gratifying.”

As per tradition, the winners of the men’s and women’s races collected massive five-pound lobsters from Larsen’s Fish Market as their prizes. The winners of the kids’ divisions each earned a pair of chicken lobsters. When nine-year-old Jack Lionette of Chilmark stepped up to collect his first-place lobsters, race organizer Hugh Weisman noted the “pretty amazing” time nine-year-old Jack had run: 19:58.

“Holy smokes,” someone in the crowd said. “Damn,” said another.

Jack, who also won his age division last year, said he was “definitely trying to break sub-20,” and had been “sprinting the whole way.” He credited part of his success to a pre-race dinner of spaghetti and meatballs, and ultimately has his sights set on the course record itself (14:38).

Though Jack was the youngest Vineyarder to cross the line first, Michael Schroeder, 19, of West Tisbury took the top overall spot for Islanders, finishing 11th with a time of 18:14.8. Emma Mushnick, 26, of Vineyard Haven, posted the fastest Vineyard time in the women’s race, running a 20:46.85 to take 61st overall and third in her age group.

This year’s field was the largest in race history, with more than 1,600 entrants completing the 5K course. Some were familiar faces, like the purple-shirted MacMaster clan from Pennsylvania. This year, 29 MacMasters took part in the day’s events.

“This year we’re stretching it into in laws,” Keegan Skidmore, 31, said before the race. Mr. Skidmore is himself a recent MacMaster in law, and did the family proud by placing seventh overall and second in his age group.

One group wore pink tutus and matching antennae-like headbands, which complemented the official black race shirts they wore.

“It’s our 10th year running it this year,” said Jessica Donahue. “Last year, when we were running it we decided we needed to do something special.”

But whether a competitor, a spectator or a volunteer, everyone at the Chilmark Road Race finds a way to make it their own.

Susan Brown of Edgartown hadn’t run the race since 1980.

“Today I am 70 years old, one month and one day,” she said. “My goal was to finish, and finish in under an hour. And I did it. I’m still standing.” Then she was off to collect her award, for placing third in her age group, before heading home to celebrate the milestone.

Nathalia Garroway, (22 months old) wearing a floppy sun hat and too-big race shirt, toddled across the finish line with her parents Christopher Garroway and Nadia Popova.

Mr. Garroway and Ms. Popova had intended to bring their two-month-old along as well, ultimately deciding it was too hot for the infant to be outside. But Nathalia was up to the challenge.

“She only stopped once to pick some flowers,” Mr. Garroway said.

Photo gallery of the road race and a complete list of finishers.