Westport is a very pretty coastal town near the Rhode Island border, with roads winding along the beach, the Westport River, pastoral farms, and tony golf courses. We’ve designed two great running loops in Westport: one along the roads paralleling Horseneck Beach and out to Gooseberry Island, and another in the coastal hamlet of Acoaxet.
Horseneck Beach/Gooseberry Island Loop: This is a 4.3 mile run with great water views the whole way and very little traffic! The route is a straightforward 1 mile along East Beach Rd., and then a 2 mile out and back on Gooseberry Island. For more length, combine with a run on Horseneck Beach or on West Beach Rd., paralleling the beach.
Acoaxet Loop. This is a straightforward 4-mile loop on some very pretty roads, with a combination of coastal views, farmland, a golf course, and nice homes. A good starting spot is the Harbor Inn on Acoaxet Rd. The first 3/4 mile is a jaunt out to The Knubble (nice views), then doubling back, onto Atlantic Ave. with nice coastal views. At the end, turn RIGHT, heading north on Howland Rd. for ~1 mile. Just past the chapel, RIGHT on Cross St. for 0.6 miles, then RIGHT on River Rd., heading back toward the water to the Harbor Inn. Longer option: head north on River Rd. No shoulder, but pretty and runnable.