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Things to Do in Boston: Outdoor Adventures

By Leigh Harrington on 05/12/15, updated 12/01/16
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Boston is not located at the foothills of the Rocky Mountains, nor does it find itself pounded by the wild surf of the Pacific Ocean, which means that extreme adventures in this city are typically off the table. However, within a very small area that is coastal, wooded and mountainous, Boston offers moderation in all things: grand hills, rushing rivers, lapping ocean, forested hiking trails, and historic islands. Those with active lifestyles looking for soft to moderate adventures have traveled to the right destination.

Spring, summer and fall are prime seasons for adventure. Cool breezes make activities on open water, like cruising, speedboating or roaming harbor islands ideal for sweaty Northeast summers. Head for Boston Harbor, where ferries, passenger ships and old-fashioned sailing ships wait at wharves from Charlestown down to Black Falcon Terminal in South Boston. Hiking activities at nature reserves like Arnold Arboreutum, the Emerald Necklace and Blue Hills Reservation during a New England autumn offers miles of scenic views in a kaleidoscope of fiery and golden tones.

Essentials to pack for these outdoor adventures:

  • Sunglasses and sunscreen, even in cooler weather if you're out on the water
  • A waterproof windbreaker because Boston weather can change on a dime
  • Sneakers or boots, whether you're walking on cobblestones or uphill at Great Blue Hill
  • Plenty of water; it's hard to find when you're off the beaten path
Arnold Arboretum

Arnold Arboretum on Lilac Sunday (©Arnold Arboretum at Harvard University)

Attractions

Arnold Arboretum

Allow yourself ample time to explore these 281 acres. You can climb—and roll down—hills, jump across streams, ride your bike, and walk and walk and walk. For adventure seekers with a love for the great outdoors, this is your hangout.

Boston Harbor Mini Speed Boats

Boston Harbor Mini Speed Boats cruise down Fort Point Channel by the Boston Tea Party Ships & Museum (Courtesy Boston Harbor Mini Speed Boats)

Activities

Boston Harbor Mini Speed Boats

With so many harbor cruise options available to travelers to Boston, it's hard to know which one is a good fit. This one suits moderate adventure seekers who'd also like to learn a few fun, historic facts. Hardcore history buffs and/or adrenaline junkies need not apply.

Boston Harbor Islands

(©Tom Kates/Boston Harbor Island Alliance)

Attractions

Boston Harbor Islands

Did you know? One of Boston's best kept secrets is its Boston Harbor Islands National Recreation Area. A ferry takes passengers to Georges Island, the park's hub; on this island, Fort Warren is a spectacular and spooky landmark for investigation. From here, catch a shuttle boat to smaller islands like Bumpkin and Grape.

Charles River Canoe & Kayak

(©Leonardo Dasilva/Flickr cc license)

Activities

Charles River Canoe & Kayak

Row, row, row that boat, and don't worry about falling in. The quality of the Charles River has significantly improved since The Standells' 1966 hit "Dirty Water" came out, thanks to the Charles River Watershed Association. Kayaks, canoes, rowboats, paddle boards and paddle boats are available for rent, so pick your fun and get moving.

Bunker Hill Monument

(©FayFoto)

Attractions

Bunker Hill Monument

After walking the Freedom Trail to reach the Bunker Hill Monument in Charlestown, the biggest adventure you'll have here is climbing all the way to the top. We hope your legs are ready!

New England Aquarium Whale Watch

Spot a whale on a New England Aquarium Whale Watch (©S. Cheng)

Activities

New England Aquarium Whale Watch

Steady your sea legs. This three-hour voyage takes you all the way out to Stellwagen Bank in Massachusetts Bay, and often that means the very tip of Cape Cod. Hunting down minke, finback and Humpback whales takes effort, but the thrill of seeing one breach the surface is totally worth it.

DCR Blue Hills Reservation

(©Niklas Tenhaef/Flickr CC license)

Activities

DCR Blue Hills Reservation

At 635-feet Great Blue Hill is a mountain climber's holiday, but moderate exercise for the rest of us. Expect incredible views of greater Boston and the city itself. Trails crisscross the reservation's additional 7,000 acres with habitats that range from meadows to woods, and there's ample opportunity for wildlife viewing.

Boston Bike Tours by Urban AdvenTours

Boston Bike Tours by Urban Adventours parks it near the TD Garden and Zakim Bridge (©Derek Morrison/Flickr CC license)

Activities

Boston Bike Tours by Urban AdvenTours

Yes, this is America's walking city, but it's now pretty easy to bike around town, too. Whizz by popular sights in Boston or Cambridge, or take a more relaxing ride through FiDi and the Seaport District at dusk. Helmets, included!

Liberty Fleet of Tall Ships Boston Harbor Sails

Liberty Star and Liberty Clipper (©Liberty Fleet of Tall Ships)

Activities

Liberty Fleet of Tall Ships Boston Harbor Sails

How often do you get to hoist and haul the sails of a legitimate tall ship?

Boston Harbor Cruises' Provincetown Fast Ferry

Provincetown Wharf (©MOTT)

Activities

Boston Harbor Cruises' Provincetown Fast Ferry

This ferry cruises across Massachusetts Bay to the very tip of Cape Cod in 90 minutes, and this quick day trip offers a drastically different environment than what you find in Boston. Wear comfortable shoes, because when you get to P-town you'll be walking Commercial Street, the beaches of the Cape Cod National Seashore and more.

Emerald Necklace

(©Todd Van Hoosear/Flickr, Creative Commons)

Attractions

Emerald Necklace

Bike it or hike it, this seven-mile park starts in Back Bay and journeys all the way to Boston's Dorchester neighborhood. It's a great place to keep up your marathon training while traveling.

Frog Pond Ice Skating

(©AlanH20/Flickr, Creative Commons)

Activities

Frog Pond Ice Skating

Ice skaters of all levels are welcome to slip, slide and glide as much as their hearts please.

The Rose F. Kennedy Greenway

North End Parks section of the Rose Kennedy Greenway (©Rose Kennedy Greenway)

Attractions

The Rose F. Kennedy Greenway

Walking the Greenway is a scenic way to burn off those calories while catching up with a friend.

Avid sailors can embrace the freezing temperatures while partaking in an entirely new experience, Frostbite Sailing. If the cold isn't your thing, you can wait to sail the Boston Harbor in the warmer months.

Weston Ski Track

(Courtesy Weston Ski Track)

Activities

Weston Ski Track

Weston Ski Track offers more than nine miles of snow-covered trails for cross-country skiing and snowshoeing and stays open after dark for the night owls.

Charles River Esplanade

(©Paul Gelsobello)

Attractions

Charles River Esplanade

Whether going for a walk, jog or run, this pathway along the Charles offers up breathtaking views, no matter what the season.

deCordova Sculpture Park and Museum

DeWitt Godfrey, "Lincoln," 2012. (Photo Alison Abbott)

Attractions

deCordova Sculpture Park and Museum

DeCordova is an artistic type of outdoor adventure. You'll find yourself weaving throughout incredible sculptures, and in the winter you can even snowshoe through the park on a guided tour.

Boston Common

Boston Common near Tremont Street with the Massachusetts State House in the background. (©Ingfbruno/CC license via Wikimedia Commons)

Attractions

Boston Common

A spacious place to explore, the Boston Common has wonderful landscaping to take in as well as plenty of pathways for walking and jogging. When there's snow on the ground, the Common provides excellend hills for sledding with family and friends.

Skiing and snowboarding are two great ways to get your blood and adrenaline pumping throughout the winter season. With such a short drive from Boston, the Blue Hills Ski Area makes for a perfect day getaway.

Map of Things to Do in Boston: Outdoor Adventures