Things to Do in Boston: Outdoor Adventures

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

Founded in 1872 and administered by Harvard University, the historic arboretum designed by Frederick Law Olmsted is a great escape from the city, and consists of 281 acres filled with trees, flowers, shrubs, vines and plants from around the globe. Open daily sunrise to sunset.

Boston Harbor Mini Speed Boats

Not too many people get to captain their own ship in Boston’s animated inner harbor. For 90 minutes, take an F-13 mini speedboat for an at-times zippy water-view tour, passing by such sights as the USS Constitution, East Boston Shipyard, Fort Independence, and the John F. Kennedy Library at Columbia Point.

Boston Harbor Islands

This readily accessible National Park is a true gem, boasting 34 islands in all and 12 open to the public. Woodland, marshes and rocky beaches compose the terrain, while offering solitude and magnificent views of the downtown skyline.

Charles River Canoe Kayak

Breeze along the Charles River and/or Boston Harbor in canoes, kayaks, and other water-bound vessels, no matter your level of experience, whether it’s your first time or you’re used to paddling in Pacific-size waves. Features canoe, kayak, paddle board and rowboat rentals, lessons, demos, and tours.

Bunker Hill Monument

Freedom Trail attraction. One of Boston’s most iconic sights is, ironically, a misnomer: the Bunker Hill Monument actually sits atop Breed’s Hill, where the American Revolution’s Battle of Bunker Hill took place in 1775.

New England Aquarium Whale Watch

New England Aquarium and Boston Harbor Cruises take you out to marine sanctuary Stellwagen Bank where migrating humpback, finback and minke whales stop and feed. Naturalists narrate the journey aboard a comfortable high-speed catamaran. Departs March 23-Nov. 17, detailed schedule online.

DCR Blue Hills Reservation

One of the best places to hike in the Boston area, Blue Hills features 100 miles of trails and a topography of forests, marshes, meadows and ponds.

Boston Bike Tours by Urban AdvenTours

These guided boutique-style bicycle tours offer exercise and sightseeing. Tours include Tour de Boston, Tour de Cambridge, Funway to Fenway and Emerald Necklace Tour. Tours depart daily and by appointment; full schedule on website.

Liberty Fleet of Tall Ships Boston Harbor Sails

Two majestic schooners offer passengers adventure, New England romance, and a fun time for families—you even get to hoist the sails. Departs June 3-Sept. 24, daily at 10:30 am, noon, 12:30 pm, 2:30 pm, 3 pm, 4:30 pm, 6 pm and 6:30 pm.

Boston Harbor Cruises' Provincetown Fast Ferry

Hit the high seas at high speeds on this catamaran that blazes a scenic route Massachusetts Bay from Boston all the way to Provincetown. Just 90 minutes in duration, ferry features a motion control system, satellite TV and a cash bar. Departs June 8-Aug.

Emerald Necklace

Landscape architect Frederick Law Olmsted left a legacy here in Boston with his seven-mile-long chain of parks known as the Emerald Necklace. Lightly manicured to look natural, the green spaces are actually a feat of strategic urban planning.

Frog Pond Ice Skating

Located within the Boston Common, the frozen Frog Pond provides a festive place to ice skate on a crisp winter day. Open M 10 am-4 pm, Tu-Th and Su 10 am-9 pm, F-Sa 10 am-10 pm. Admission: free-$6; skate and locker rental: $6-12.

The Rose Kennedy Greenway

The Greenway, as locals call it, spreads across 15 acres in the heart of the Financial District. It was created after the Big Dig, which sent previously elevated highways here underground, and it is inspired by other urban green spaces like New York City’s Battery Park City and Amsterdam’s Vondel Park.

Boston Sailing Center

Stop here to practice your sailing all year round with the beautiful Boston scenery surrounding you. The Boston Sailing Center allows for some pretty unique opportunities for those in the sailing world. Here, this water sport is not just limited to the warmer weather months.

Weston Ski Track

Skiing and snowshoeing are two fantastic ways to get your heart pumping during the winter season. Explore more than nine miles of snow-covered trails during the day or at night. Weston Ski Track also offers lessons for beginners or those who just want to brush up on their skills. 

Charles River Esplanade

Located along the Boston side of the Charles River Basin between the Longfellow and Boston University bridges, this green space is filled with people year-round. The open area surrounds the Hatch Shell, which hosts summer concerts, while a jogging path runs riverside along the park’s length.

deCordova Sculpture Park and Museum

This former mansion, now acclaimed art destination, showcases rotating exhibitions of contemporary art and sculpture by international, national and New England artists. Encompassing 30 acres just 20 miles from Boston, the outdoor Sculpture Park provides a constantly changing landscape of more than 60 large-scale sculptures.

Boston Common

Freedom Trail attraction. America’s oldest public park and part of the Emerald Necklace, the 50-acre Boston Common was set aside in 1634 as a military “trayning” ground and pastureland, and it has always been a gathering place for residents who convene for rallies or recreation.

Blue Hills Ski Area

Located only half-an-hour away from Boston, Blue Hills Ski Area in Canton is quite the ideal place to hit the slopes whether on skis or a snowboard. If you're really itching to get out into the fresh snow, but have no where to go around your apartment, then this is the perfect day escape for you.