This affluent coastal town features a pretty center, the white-sanded Singing Beach, and several scenic vista points. For running in Manchester-by-the-Sea, we recommend designing your own route, incorporating Beach Rd., passing Masconomo Park out to the beach (1.5 miles from town center), and the quiet roads leading by spectacular homes out to vista points: ~ 1 mile along Proctor St., and ~1 mile along Masconomo St. Singing Beach is about 1 mile, but the softer white sand is not great for running. Note: Parking can be a challenge in summer.
Another good running option in the area is the Coolidge Reservation, run by the Trustees of Reservations. A 1-mile one-way trail runs from the parking area to the top of Bungalow Hill, around Clarke Pond to Magnolia Beach, and to the spectacular Ocean Lawn.