Cape Ann Loop Trail is a standout hiking destination in Rockport, Massachusetts, covering 5.5 miles with 300ft of elevation change. Stats: 5.5 miles, 300ft gain, Moderate. Type: Loop. Surface: Rock/Dirt. Time: 2-3 hours. Fee: Free. Dogs: Yes. Permit: No. Wildlife: harbor seals, deer, foxes, double-crested cormorants. Best seasons: Dramatic coastal granite trail on Cape Ann. Pack water, layers, and appropriate footwear. Conditions vary across Massachusetts. Leave No Trace: stay on trail, pack out all waste, respect wildlife.