A father and a daughter hike on Boston Harbor Islands

Adventure Guide to the Boston Harbor Islands

Photo: Boston Harbor Now

Explore the multiple, diverse sites of this sprawling, aquatic urban escape for immediate seaside hiking, fishing, paddling and camping.

Don’t make the mistake of assuming you have to head for the hinterlands to have an outdoor adventure—some of the country’s biggest cities hide surprising opportunities for playing outside. Take Boston: A collection of islands and peninsulas (34, to be exact) sit in Boston Harbor, offering 50 square miles with everything from backcountry camping, hiking, and sea kayaking to historic sites and Atlantic beachcombing. And it’s all a T ride away, plus a ferry (or paddling excursion) over to the islands. 

Boston Harbor Islands, a national recreation area plus a state park, comprise a wide variety of ecosystems and landscapes, from rocky shorelines to sandy beaches to tidal mudflats. Plenty of wildlife make their homes here. The islands serve as important habitat for birds, including ducks, terns, sandpipers, hawks, and plovers, plus migrating songbirds and wintering waterfowl. On land, you might spot garter snakes, skunks, raccoons, and muskrats. Just offshore, jellyfish, harbor seals, and the occasional whale swim. 

The islands are also home to fascinating human history, beginning with the Indigenous peoples who lived in the Boston area for thousands of years. Prior to the arrival of Europeans, the harbor islands were part of the territory of the Massachusett Tribe, the Mashpee Wampanoag, and the Nipmuc. Later, they formed a link on the Maritime Underground Railroad, a boat-based escape route for people fleeing slavery in the South. Some of the first Black Union Army regiments camped on Gallops Island during the Civil War; the islands also held recruiting and training camps, prison camps, and defensive structures during that time. A handful of Civil War-era forts and World War II structures remain in the park for exploration.

Getting There

Boston Harbor Islands has sites scattered across Boston Harbor and Dorchester, Quincy, and Hingham bays, plus mainland destinations from downtown Boston to Hingham. The mainland’s Welcome Center is accessible from the T (Aquarium stop, on the Blue Line). Four of the islands can be reached by ferry: Spectacle, Georges, Peddocks, and Thompson. Summer brings full ferry service, while access is more limited in spring and fall, and you can only reach the islands in winter on special occasions. Private boaters and kayakers can sail/paddle over to some of the other islands on their own, though public moorings and slips on most islands must be reserved ahead of time. 

A guide teaches kayak tours Photo: Boston Harbor Now

Top 5 Adventures at Boston Harbor Islands

Here’s how to get the most out of the abundant outdoor recreation opportunities in the parks.


Lovell’s Island may be small, but low tide more than doubles its acreage—and reveals a wealth of tidepools. Wander (carefully!) among them to find barnacles, kelp, lobster, periwinkles, and crabs. There are also a few short trails here exploring sand dunes and woods, plus a small campground and swimming beach. (The park concessionaire has offered ferries to Lovell’s Island in the past, but the pandemic paused that service; check their website for the latest schedules.)


Like any good saltwater destination, the Boston Harbor Islands offer lots of opportunities to cast for striped bass, bluefish, and winter flounder. Castle Island (actually a peninsula) just off South Boston draws anglers with its large, L-shaped pier and fish-filled inlets off Pleasure Bay. Or check out the new-in-2021 fishing pier on Deer Island (another peninsula) just south of Winthrop. No matter where you go, you’ll need a Massachusetts recreational saltwater fishing permit if you’re 16 or older.   


The islands’ historic lighthouses draw plenty of admirers, and there’s no better way to see them than from the sea. The park runs a two-hour cruise that sails past three of the stations: Long Island Light, Graves Light, and Boston Light on Little Brewster Island. The latter’s claim to fame is being the country’s oldest continually used lighthouse, dating back to the American Revolution. Onboard guides tell the stories behind the structures. 


For easy access to a backcountry camping experience, book a site on Peddocks Island. Though the island, one of the park’s largest, feels remote, you can still access it directly by ferry in the summer. Campsites sit in grassy meadows or under hardwood trees, and you can also sleep in one of the island’s cozy yurts. More Peddocks highlights: hiking trails that traverse coastal forests and marshes, a turn-of-the-20th-century fort, and a restored World War II-era chapel. 


One of the closest islands to Boston, Spectacle Island is laced with 5 miles of trails that trace its shoreline, head up its high points (two glacially carved hills called drumlins), and explore everywhere in between. The 1.7-mile Perimeter Trail loops around the entire island, granting views of Boston Harbor, the city skyline, and the other islands. The North Drumlin Trail winds 1.8 miles up to the highest point in the harbor, where you’ll find a gazebo perfect for taking in the vista. Spectacle is also one of the most developed islands, with a marina, visitor center, café, and swimming beach with a lifeguard. 

Sea kayaking

Most of Boston Harbor Islands make for great ocean kayaking, but one standout trip is an overnight to Bumpkin Island, a 62-acre island tucked into Hingham Bay. Sea kayakers can launch from either Hingham Beach or Hull on the north side of the Nantasket Peninsula. Paddle to the island to walk rocky beaches and check out the remains of a historic stone farmhouse, then settle in for the night in the island’s campground (reservations required). Note: This is not a beginner’s paddle. The potential for high winds and rough waters, plus the fact that Boston Harbor contains active shipping lanes, makes this trip one for experienced kayakers only. 

All articles are for general informational purposes.  Each individual’s needs, preferences, goals and abilities may vary.  Be sure to obtain all appropriate training, expert supervision and/or medical advice before engaging in strenuous or potentially hazardous activity.