Just past the see-and-be-seen towns of the Hamptons is Montauk, a surfer's and fisherman's hamlet located at the eastern tip of Long Island, which hosts this laid-back triathlon every summer. Athletes start in the calm salt waters of Lake Montauk and then wind their way around 22 miles of quiet roads, passing the Montauk Lighthouse, and wrapping up with a hilly 10k run. If you do want to experience the emerging Montauk party scene, head out to bars like the Surf Lodge, Ruschmeyer's, and the Sloppy Tuna.
The Course: Olympic distance (1-mile swim, 22-mile bike, 6.2-mile run)
When: June 7, 2014
Where: Montauk, NY