Cape Cod, MA

Hyannis Port Loop

Author photo

This is a great little loop of the affluent summer community of Hyannis Port, which can be done standalone or combined with our Hyannis route. It includes a peek at the historic Kennedy Compound, some lovely waterfront sections, and spectacular homes. One benefit of this run is part of it is on roads that cars are discouraged from taking.

Squaw Island Rd. Author photo

A good starting point is the Keyes Memorial Beach parking lot (parking is tough on area streets). A pedestrian path follows Ocean Ave., with great water views. Continue following the water (LEFT on Hyannis Ave., LEFT on Iytanough, RIGHT on Irving), passing the Kennedy Compound at Longwood. Turn LEFT on Dale, following the water along Squaw Island Rd. Great views of the water and spectacular waterfront homes. Turn around at the ‘private road’ gate. Then, explore the gorgeous residential area above the water, taking the hill up Hawthorne Ave. to Saint Andrew’s By The Sea Church and the Hyannisport Golf Club. Great views! Enjoy a tour of these gorgeous homes, using Massachusetts Ave. & Edgehill Rd. to make your way back to Ocean Ave. and the start.

Hyannis Add-On: You can combine this with our Hyannis route. Various ways to do it, using Sea St., Old Colony Rd., or Ocean Ocean Ave. (~1 mile back to Hyannis). A longer way is from Kalmus Park Beach on our Hyannis route to Keyes Beach (use Hawes-Etsey-Gosnold-Sea). Or, from Veterans Park, take Gosnold Rd.

  • 3.8 miles (6.1 km). Can be combined with our Hyannis route
  • 103 feet
  • Keyes Memorial Beach parking lot, or from Hyannis for longer route
  • Parking can be tricky in Hyannis Port