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Eight great outdoor adventures in Boston

Mara VorheesLonely Planet author

Let’s go outside and play! Everybody knows that Boston puts on a good art show and gives an excellent history lesson. But this compact city is also blessed with beaches and bike trails, islands and ice rinks, rivers and running routes, not to mention one vast, blue beautiful harbor.

So when you’re ready to see Boston from a different point of view – with the sun in your eyes and the wind in your face – here are some ways to do it.

Harnessing the wind

Sailing around the Boston harbor. Image by Walter Bibikow / AWL Images / Getty Images

Get on the water for the best perspective of Boston’s skyline. Image by Walter Bibikow / AWL Images / Getty Images

Feel the wind in your sails and admire Boston’s magnificent skyline from the water. Experienced sailors can rent a three- or four-seater sailing boat for a jaunt around the Boston Harbor (Courageous Sailing) or the Charles River Basin (Community Boating). If you prefer to leave the hard work to the professionals, book a trip on the Liberty Fleet, classic 125-ft schooners that take passengers cruising around the harbor.

Cycling along the Charles River

The best way to see Boston is from the seat of a bike. Nowadays there are painted and protected bicycle lanes along many popular cycling routes, though it can still be tricky for novice riders to navigate the crowded city streets. The Charles River Bike Path is an excellent alternative. This fantastic off-road circuit runs along both sides of the Charles River between the Museum of Science and the Mt Auburn St Bridge in Watertown (five miles west of Cambridge). The route offers an excellent overview of Boston, as you’ll ride through Beacon Hill and Back Bay, past Fenway Park and the famous Citgo Sign, and alongside the Harvard and MIT campuses. The round-trip is 17 miles, but the 10 bridges in between offer ample opportunity to turn around and shorten the trip.

Following in the footsteps of Boston marathon runners

Running in Boston. Image by Samuli Siltanen / iStock / Getty Images Plus

Running over the Charles River. Image by Samuli Siltanen / iStock / Getty Images Plus

Clearly, pounding the pavement is a popular pastime in Boston, where the biggest annual event is a marathon. If you prefer to stay off the streets, miles of trails through Boston’s parks offer an easy escape from the traffic.  The most popular running route is along the Charles River Esplanade, a lovely landscaped waterside park that stretches for almost three miles along the south shore of the river. A series of paved paths weave their way from end to end, winding around playing fields, playgrounds and exercise stations, and eventually connecting to the Charles River Bike Path for longer runs.

Getting out of town on the Minuteman Bikeway

The best of Boston’s bicycle trails is the Minuteman Bikeway, a wide, straight paved path that leads through Boston’s northern and western suburbs. The Bikeway starts in Arlington (near Alewife station), leading 5 miles to Lexington center, then traversing an additional 4 miles of leafy scenery before it terminates in the rural suburb of Bedford. Along the way, you’ll pass pretty Spy Pond, bird-filled Great Meadows and historic Battle Green – the site of the first skirmish of the War for Independence.

Exploring the Boston Harbor Islands

Trails galore to explore on the lovely Boston Harbor Islands. Image by Amy Riley / iStock / Getty Images

There are trails galore to explore on the Boston Harbor Islands. Image by Amy Riley / iStock / Getty Images

The Boston Harbor is sprinkled with 34 islands, many of which are open for trail walking, bird watching, fishing and swimming. The destinations that are easiest to access are Georges Island, home to a 19th-century fort that is ripe for exploration, and Spectacle Island, site of a glorious 360-degree lookout from the islands’ highest point. From these hubs, there are ferries to some of the smaller islands, where countless adventures are waiting to happen.

Swimming and plane-spotting from South Boston beaches

The South Boston waterfront is lined with beaches that are sandy, scenic and swimmable – if you can bear the frigid water! The best is perhaps Castle Island, as the park has a fishing pier, a playground, a popular lunch stop (Sullivan’s) and a star-shaped fort to explore. The beach also provides an excellent vantage point to watch the airplanes taking off or coming in low to land at Logan airport, which is just across the harbor.

Kayaking and canoeing on the Charles River

Kayaking in the Charles River. Image by APCortizasJr / iStock / Getty Images Plus

Kayaking down the Charles River. Image by APCortizasJr / iStock / Getty Images Plus

Slow down: rent a canoe or kayak from the Charles River Canoe & Kayak Center and paddle around the picturesque waterway. Experienced paddlers can venture out to the harbor, but the river and basin are unbeatable for city views and a leafy aspect. There are outlets in Cambridge (near Kendall Sq) and Allston (near Harvard Sq), which allow for an excellent one-way five-mile trip between the two rental centers.

Winter sports

In Boston there is plenty of winter to go around. The snow usually arrives in December and sticks around until March, if not April. While Bostonians maintain a long tradition of whingeing about the weather, they also know how to endure winter: that’s right, put on your big boots and your warm, woolly hat and go out and play in the snow. Skating on the Boston Common Frog Pond is a long-time Boston tradition, while Community Ice Skating @ Kendall Square is a less crowded though less atmospheric alternative. Both facilities offer skate rental. On the outskirts of town, the Weston Ski Track has 15km of trails for cross-country skiing and show-shoeing, while the Blue Hills Ski Area 10 runs for downhill skiing.

This article was originally published in 2010, and updated in 2015.

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