Island’s greatest sporting event is back: 10K on for June 20

Among the hallmarks of Shelter Island’s 10K Race is Director is Mary Ellen Adipietro’s 27th year at the helm and the 47th year of the race.

So, as the Shelter Island 10K Run/5K Walk is poised for its 47th year on June 20, organizers are looking ahead three years to what will be the 50th anniversary of the event.

Ms. Adipietro began leading the organizers of the race in 2000 and her eyes are focused on that 50th anniversary, making alliances with other prominent races throughout the area for what she aims to make a grand celebration.

Ms. Adipietro and husband Dr. Frank Adipietro, the voice of the race, have brought prominent runners to participate, including Bill (“Boston Billy”) Rodgers, a former Olympian and winner of four New York City Marathons and four Boston Marathons.

At 78, he still loves the sport, while acknowledging he is likely to participate in the 5K this year, not the 10K, on a course around the Island that many have said — including national magazines — is the most beautiful in America. “I’m on creaky legs,” Mr. Rodgers said.

What brought him to the sport back in the early 60s and still keeps him in the game, he said, is friendships. “I like to hang out with people,” he put it simply. That’s what brought him to Shelter Island’s signature sporting event for all these years. He had met Dr. Adipietro at a Boston Marathon and they began talking. Over time, Dr. Adipietro told him about the annual Shelter Island race, and Boston Billy has been coming back to the Island for years.

Gen Z people are changing the sport, Mr. Rodgers said, referring to those between the ages of 14 and 29, and it’s become more global. The emergence of women in running continues to increase since Joan Benoit Samuelson became the first woman marathon runner to win gold, at the 1984 Olympics in Los Angeles. She became an inspiration to women to embrace running and continues in that role today. She is another former Olympian who has run the Shelter Island course for many years.

Mr. Rodgers also sees more older people participating in the “ultimate outdoor sport” than when he started running. “Our sport is in a brave new world,” he added. 

Mr. Rodgers came to know Fred Lebow, who took over management of the New York Marathon, which attracted 55 finishers in 1970 and 59,225 finishers in 2025.

Because of his passion for running, Mr. Rodgers made friends from about 200 countries around the world, including the late Grete Waitz, the Norwegian marathon runner and former world record holder in the New York City Marathon. 

James “Jimbo” Theinert has a long history with the 10K that started when he was a boy in school on the Island and volunteered to stuff complimentary gift bags that race participants receive. Through the years, his involvement has grown. Now a teacher at the school and the developer of its externship program, he’s involving today’s students in the event that means so much to him. “I’ve been through the cycle,” Mr. Theinert said about his his love for the event.

He reached out to Eban Howell, a consultant and principal of Santiago/Studios for assistance in working with students   because of Mr. Howell’s enthusiasm about running and motivating others. He has been an adviser to companies on use of media and communications serving clients including American Express, Digital Content Next, Ford Motors, Johnson & Johnson, Tommy Hilfiger International and Tribeca Enterprises. Not surprisingly, it was running that brought Mr. Theinert and Mr. Howell, a certified running instructor, together.

Mr. Theinert describes getting students involved in the 10K as laying the foundation for them to serve in different capacities for the Race Committee. He works with a team of volunteers, including many students, placing flags along the last mile leading to Fiske Field where the race ends. That mile is known as “Joey’s Mile,” a tribute to Mr. Theinert’s brother, Lt. Joseph Theinert, who was killed in action while serving in Afghanistan.

“This is still a meaningful event for our community,” Mr. Theinert said. In addition to building toward the 50th anniversary of the race, he hopes to bring back events such as the pasta dinner the night before the race where runners load up on carbs and camaraderie.

Jaxson Rylott, 19, is a Shelter Island High School graduate studying communications and media studies at Quinnipiac University. Jaxson began participating in the event when he was in elementary school. What really got him involved with running was joining the running club then led by teacher Bryan Knipfing.

“Living on Shelter Island, it’s impossible to not know about the 10K race,” he said. “As somebody interested in running, it was hard to say no,” Jaxson said. He first ran the 10K course during the winter and said the practice running he did then was “a much different experience than running it during the actual race. The easiest part of the course for me is when I get up the first hill a little past the Whale’s Tale and the one mile mark.”

That’s when you get over the hill and encounter nice downhill running and “a beautiful view looking over the water,” Jaxson said. In 2021, Jaxson won the 5K part of the course when he said he had no expectations but was “just going out to run for fun.” His first 10K race was another “special moment. Running that course with people all around you is a different experience,” Jaxson said. “It wasn’t like we were all individually running but rather running it together as a community.”

His advice to others considering the race is to get a couple of friends willing to run the course together. “Even if your friends say no, then sign yourself up. You won’t regret it.”

You can sign up now at https://events.elitefeats.com/26si10k.