Rockport lies at the tip of Cape Ann, about 40 miles northeast of Boston. The town is known for its fishing harbor, granite quarries, boulder-strewn beaches, and the famously paintable “Motif #1” shack at the end of Bearskin Neck. The best running in Rockport is a route along the water near the town center. Choose any portion of the ~3.3 mile one-way route we’ve mapped, featuring the prettiest waterfront roads. Coming off Rt. 127A, run along Marmion Way and Garden Rd., past pretty homes, with views to Gap Head and the Headlands. At 1.3 miles, get into Atlantic Ave., and then do a jaunt out to Bearskin Neck, which features quaint shops and galleries. You can continue for another mile north, along Beach Rd. and then Granite St. with Front Beach and water views up to the Rockport Granite Pier. Note: Bearskin Neck is super busy in summer.
It’s also fun to run/walk along the pretty streets of Rockport center, which features fun shops, restaurants, and historic buildings.