We may earn a commission from links on this page, at no cost to you. Disclosure
The best outdoor things to do in Boston are walking the 2.5-mile Freedom Trail, following the Harborwalk along the waterfront, sailing or kayaking on the Charles River from the Esplanade, hiking the trails of the Boston Harbor Islands, walking the Emerald Necklace parks out to the Arnold Arboretum, and circling Castle Island in South Boston. All of them are inside the city, most are free, and the harbor islands are the only one that needs a ferry ticket.
This guide is about getting outside and moving: walking, paddling, cycling and hiking. For a slower day of gardens and quiet corners, see our guide to relaxing things to do in Boston, and for boats, cruises and whale watches, see things to do on the water.
Walk the Freedom Trail
The Freedom Trail is a 2.5-mile red line in the sidewalk that links 16 historic sites, from Boston Common to the Bunker Hill Monument in Charlestown. Following the line is free. It runs one way and does not loop back, so plan how you will get home from Charlestown: the MBTA inner harbor ferry from the Charlestown Navy Yard to Long Wharf costs $2.40 and turns the return into a short harbor crossing.
Follow the Harborwalk
Boston Harbor Now describes the Harborwalk as a near-continuous, 43-mile linear park along Boston's shoreline, connecting the waterfront neighborhoods. You do not need to walk much of it to see the harbor. A good stretch runs from the North End past the downtown wharves and the New England Aquarium into the Seaport, where the wooden grandstand outside the Institute of Contemporary Art is part of the Harborwalk and open to anyone. To see the same shoreline from the water, a narrated harbor sightseeing cruise is bookable on Viator.
Sail or kayak on the Charles River
Community Boating has taught sailing from its boathouse on the Charles River Esplanade since 1946, at 21 David G. Mugar Way, and rents sailboats and kayaks to non-members by the day. Upriver, Paddle Boston rents kayaks, canoes and paddleboards at its Allston/Brighton location on Soldiers Field Road in Boston, one of seven rental sites around the region. Both are seasonal, so check the dates before you go.
The Esplanade itself is the city's riverside park, a long strip of lawns and paths on the Boston bank of the Charles, good for a run or a walk at sunset.
Hike the Boston Harbor Islands
The Boston Harbor Islands are 34 islands and peninsulas in a national and state park, reached by seasonal ferry from Long Wharf. On Spectacle Island, 4 miles out, the North Drumlin gives views back to the skyline, and a 1.5-mile perimeter trail is the park's only fully accessible island trail. On Georges Island, 7 miles out, you can explore Fort Warren, built between 1833 and 1860, including its parade ground and the Dark Tunnel.
There is no park entrance fee, only the ferry. The 2026 season ends on October 12, and the park runs a $5 ferry weekend to Spectacle and Peddocks islands on October 10 to 12. Bring water, layers and sunscreen; outside ferry hours there are no visitor centers, restrooms or drinking water on the islands.
Walk the Emerald Necklace to the Arnold Arboretum
The Emerald Necklace is a chain of parks laid out by Frederick Law Olmsted, and the Emerald Necklace Conservancy describes it as 7 miles of landscapes. The Arnold Arboretum in Jamaica Plain is the best single stop: 281 acres and more than 15,000 plants, free and open every day from sunrise to sunset. Peters Hill gives a view back to the Boston skyline. Picnics are not allowed in the arboretum, bikes stay on paved paths at 10 miles per hour or less, and dogs must be leashed. The Orange Line ends at Forest Hills, a walk from the Forest Hills gate.
Loop Castle Island and Pleasure Bay
In South Boston, Castle Island is a state park run by the Department of Conservation and Recreation, open from sunrise to sunset. Walk the short Castle Island Loop around Fort Independence, or the longer Pleasure Bay Loop, which is wheelchair accessible. Carson Beach, M Street Beach and Pleasure Bay are next to it for swimming in summer, and there is free parking in the lot near the fort. Dogs are not allowed on the beaches from May 1 to September 15.
Spend a slow hour on the Common and in the Public Garden
Boston Common dates from 1634 and is free and open every day. Across Charles Street, the Public Garden, founded in 1837 as America's first public botanical garden, has a lagoon, a footbridge and the Make Way for Ducklings statue. The Swan Boats run from mid-April to early September; in 2026 they closed on September 7 and return in April 2027.
Ride a Bluebike
Boston's bike share, Bluebikes, costs $3 for a 30-minute ride or $11.99 for a day pass with two-hour classic bike rides. Stations are spread across the city, including one at Boston Public Market. A bike is the easiest way to link the Esplanade with the Back Bay Fens and the rest of the Emerald Necklace.
Outdoor Boston by season
- Spring: Swan Boats return in mid-April; harbor ferries from mid-May.
- Summer: beaches at Castle Island, paddling on the Charles, islands every weekend.
- Fall: the best walking weather; island ferries until mid-October.
- Winter: skating at the Frog Pond on Boston Common, generally November to March, and walks in the arboretum.