From the starting line at Southampton Intermediate School, the out-and-back course takes runners south down Old Town Road before heading in a northeast direction along the tree-lined Wickapogue Road, Downs Path, and Flying Point Road. This loop and the return to Old Town Road makes up the first four miles of the course and features some minor ups and downs.
From there, runners head south back down Old Town Road and then west around Old Town Pond and Agawman Lake, making a loop around the residential roads of Coopers Neck Lane, Great Plains Road, and Halsey Neck Lane before retracing their steps back to the finish line at Southampton Intermediate School.
While they’re in the area, participants and their friends and families can take in the sights of one of the country’s most historic beach towns, where Jackson Pollock lived and painted many of his most famous works.
Known today primarily as a playground for the rich and famous, especially for many of New York’s wealthiest families, the Hamptons is home to the annual Artists & Writers Softball game, which has drawn the likes of John Mailer, Kurt Vonnegut, Paul Simon, Dustin Hoffman and others out to play in years past.
