29.3 miles: 0 hours, 51 minutes
Vacationing in the Hamptons? Montauk Highway is unavoidable. Locally owned businesses dot the road, one of Long Island’s original through highways, as it winds through communities like Bridgehampton, East Hampton and Amagansett. The east-west route also showcases the summer colony’s picture-perfect natural scenery as well as its myriad of multimillion-dollar homes.