This beloved end-of-summer tradition, started in 1989 by Dr. Louis W. Sullivan, welcomes runners and walkers of all abilities to a USATF-certified 5K course that winds through East Chop with beautiful views of Nantucket Sound in Oak Bluffs, Massachusetts. Before the main event, kids can enjoy a 25-meter dash at Washington Park, and the first 300 registered participants will receive commemorative t-shirts. Keep in mind that parking is tight near the park and harbor, so carpooling, biking, or walking to the event is encouraged; the race happens rain or shine, and strollers and leashed pets are welcome but should stay toward the back of the pack.