Great Island Trail

Eastern Massachusetts Has Some of the Loveliest Hikes in New England

"An 8.8-mile challenging loop that begins by tracing the shoreline of “The Gut,” where the Herring River meets the harbor, then climbs into pitch pine forest with cliffs that afford sweeping views of Cape Cod Bay. The route passes the former site of a 17th-century whaling tavern, traverses dunes up to Great Beach Hill, and finishes with a breezy walk along the water; although technically a peninsula, the abundance of ocean panoramas gives it an island feel." - Madeline Bilis Madeline Bilis Madeline Bilis is a writer, editor, and guidebook author based in New England. She has a soft spot for brutalist buildings and a degree in journalism from Emerson College. She was previously an assistant editor at Travel + Leisure. Travel + Leisure Editorial Guidelines