Ravenswood Park
Explore Ravenswood Park, Gloucester’s expansive woodland reserve featuring scenic carriage trails, granite boulders, and year-round natural beauty.
Halibut Point State Park
Perched at the northern tip of Cape Ann, this rugged coastal park offers sweeping ocean views, scenic trails, tide pooling, and a fascinating window into Rockport’s granite quarrying past.
Dogtown
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown’s glacial boulders, colonial cellar holes, and engraved Babson Boulders make it Cape Ann’s most fascinating untamed treasure.
Dog Bar (at Eastern Point Lighthouse)
Walk Gloucester’s iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor on one side and open ocean on the other — plus stunning views of the Dog Bar Breakwater Light.
The Trustees of Reservations
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some of the North Shore’s most treasured landscapes — open for all to explore year-round.
Greenbelt, Essex County’s Land Trust
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly trails on conserved lands—perfect for hiking, biking, and wildlife watching from dawn to dusk year-round.