Shelter Island Run

Embark on an unforgettable running experience at the Shelter Island Run, taking place on Saturday, June 20, 2026, in the picturesque setting of Shelter Island, NY. Choose your challenge from a scenic 10K or a spirited 5K, both offering a unique journey through one of Long Island's most cherished destinations. This "generational race," renowned for attracting both elite athletes and everyday runners, is celebrated for its stunning course that winds through country views, historical sites, and offers refreshing wafts of sea breeze, making it truly one of the prettiest races in America.

The 10K and 5K courses, while largely on paved roads, feature a "gently rolling" to "fast and flat" profile with some notable inclines and descents that add an engaging challenge for runners. Participants can expect well-supported routes with water stations at regular intervals (2, 4, and 5 miles for the 10K; 1.5 miles for the 5K) and a professionally staffed medical tent at the finish line. The race kicks off in the late afternoon, with the 10K starting at 5:30 PM and the 5K following at 5:45 PM, providing a memorable sunset run experience. Typical race day conditions in late June bring highs around 80F and lows around 62F, with a 15% chance of precipitation, so prepare for potentially warm and humid weather.

Starting and finishing near the Shelter Island School, the event cultivates a vibrant atmosphere, complemented by a free Kids Fun Run for younger enthusiasts. Beyond the race itself, runners are invited to a lively post-race celebration featuring a complimentary BBQ, free beer, live music, and dancing at the Island Boatyard/SALT Restaurant, making for a festive conclusion to an exhilarating day. The Shelter Island Run is more than just a race; it's a community tradition that combines athletic challenge with stunning natural beauty and a celebratory spirit.