This is a great run along the beach and pretty roads lined with iconic Hamptons estates. The route starts on Main St. from the Gubbins Perfect Fit running store. The highlight of the run is the 2-mile stretch along Further Ln., which parallels the beach and features many grand homes and estates (some blocked by fences and shrubs). You can take some of the numerous little side streets right down to the beach, which adds some mileage. Good options are Old Beach Ln. Two Mile Hollow Rd., and Indian Wells Hwy.
We’ve included two options here. The short run turns around at the end of Further Ln., for an out and back of 5.5 miles. For a run of up to 12 miles (of course you can turn around at any point), continue past the end of Further Ln., along Bluff Rd. and Marine Blvd., to Amagansett, and the small but significant Amagansett National Wildlife Refuge.
Main St. in East Hampton features numerous shops and restaurants, including two running stores operated by the Gubbins, a cycle store, and others catering to recreational activities.