Best of Beantown: 9 active things to do outside in Boston

October 15, 2015                 5m read time
Stephanie Mee


Stroll along Boston's cobblestone streets and you could get the impression that this city is just one giant open-air museum. You can hardly take a step without bumping into a historical landmark here. Delve a little further, and you'll find that the revolutionary spirit is still alive and well in the form of arts and culture, sports, and a burgeoning culinary scene. Don't be surprised to find monuments next to modern gastropubs, or history professors rubbing elbows with lobster fisherman at a beloved Red Sox game. Far from stuffy, Boston's prime seaside location also makes it a great base for those who want to hike, bike, and sail around the surrounding coastline. Now how do you like them apples?

1. Cape Cod: It's not just for relaxing

The iconic sandy path leading to Cape Cod near Boston, Massachusetts  rolf_52

The iconic sandy path leading to Cape Cod near Boston, Massachusetts 

rolf_52

 

When the weather is warm and the wind picks up, the waters around Cape Cod come alive with kiteboarders gliding across the waves. Popular kiteboarding spots include West Dennis Beach on the south coast of the cape, Joseph Sylvia State Beach off of Martha's Vineyard, and Chapin Beach, which is especially good for beginners. First timers can learn how to harness the wind with lessons from Fun Seekers or the Boston Kite School. If it's gear you're after, Air Support Kiteboarding can rent you everything you need.

2. Try the triple threat: Hike, Bike and Kayak in Boston

Boats on the Charles River between Boston and Cambridge in Massachusetts Marcio Jose Bastos Silva

Boats on the Charles River between Boston and Cambridge in Massachusetts

Marcio Jose Bastos Silva

 

Enjoy the great outdoors on the Charles River Esplanade, a 3-mile long path that follows the banks of the Charles River. Along the way you'll find plenty of places to rent kayaks or sailboats, or you can join the joggers and bikers who come here en masse during the warmer months. (Literary runners will be interested in knowing that this is a favorite running spot of Haruki Murakami, as described in his book, “What I Talk About When I Talk About Running.”)

If you happen to be here in October, check out the Charles Regatta rowing race, which features around 2,000 boats and attracts more than 300,000 locals and tourists from all over. Even if it’s not race weekend, the esplanade is still a great place to see some of the best head race teams (also known as crew) practicing. And if all that on-water action has hunger pangs setting in, warm up with a bowl of clam “chowdah” at 75 Chestnut, a local favorite for classic and contemporary cuisine.

3. A Taste of the Good Life in Wine Country

Nashoba Valley Vineyard near Boston, Massachusetts Massachusetts Office of Travel and Tourism

Nashoba Valley Vineyard near Boston, Massachusetts

Massachusetts Office of Travel and Tourism

 

Bone up on your wine knowledge and sip some great vino on a Boston City Wine Tours  excursion. Choose from South End, North End, or Back Bay locations, and visit the neighborhood's best kitchens and wine cellars, such as Legal Seafood, L’Espalier, and Gaslight Brasserie du Coin. The two-hour guided tour includes three stops where you will learn about grape growing and wine making and sample the final product. Each group is kept small to give you a more intimate experience.

4. Snap a Bird's-Eye-View of the City

An bird's eye view of downtown Boston in the winter hstiver

An bird's eye view of downtown Boston in the winter

hstiver

 

When it comes to great photo ops, the sky is the limit on a Photo Flight Tour with Noble AirVentures. This 30-minute aerial tour takes you high above Boston to snap amazing shots with either the GoPro provided onboard or your own camera. There is no set flight path, so the professional pilots are happy to fly you over all of your favorite landmarks and primo picture locations. Trust us, it's nearly impossible to take a bad shot when you're flying hundreds of feet above the city.

5. Source a Gourmet Dinner: Lobster & Scallop Diving

Grave's Lighthouse stands alone in Boston Harbor in Boston, Massachusetts Joseph Sohm

Grave's Lighthouse stands alone in Boston Harbor in Boston, Massachusetts

Joseph Sohm

 

Boston Harbor and the surrounding waters make for awesome diving spots to see such underwater sights as shipwrecks, scallop beds, and lobsters. Scuba divers of all levels can head to Grave's Lighthouse right in the harbor to see huge boulders and colorful marine life, or try diving Nahant just a few miles north of Boston to catch flounder and lobsters. Advanced divers can head to Romance Wreck, a fascinating site just off Nahant that features the remains of a ship that sunk in 1936. For those who are new to the sport, a Discover SCUBA Course with East Coast Divers, Inc. will teach you everything you need to know to safely explore the underwater world.

6. Test your nautical skills by sailing at Jamaica Pond

A biker cycles past handrails and yellow foliage along Jamaica Pond in Boston, Massachusetts LornaWu

A biker cycles past handrails and yellow foliage along Jamaica Pond in Boston, Massachusetts

LornaWu

 

Just five miles south of the city, Jamaica Pond is the largest body of freshwater in Boston. At this popular sailing and fishing spot, visitors can rent sailboats, rowboats, and kayaks or take sailing lessons to learn the basics with a guide. If you have a Massachusetts fishing license, you can also cast your line to catch lunch or dinner. After a day out on the water, stop in at J.P. Licks for local flavors of ice cream and frozen yogurt, such as apple cider and maple walnut.

7. Sink a few pints at Samuel Adams Brewery

Inside the brewery on the Sam Adams alirjd

Inside the brewery on the Sam Adams

alirjd

 

Local brewery Samuel Adams is a major source of pride for Bostonians. In just the past five years alone, the company has won more international beer tasting competitions than any other craft brewery in the world. Take a free tour to find out more about their brewing methods including dry hopping and barrel aging, and sample some of their great beers, including the Boston Ale, Cream Stout, Lager, and Double Bock.

8. Step Back in Time on The Freedom Trail

A portion of the Freedom Trail in Boston, Massachusetts Elena Elisseeva

A portion of the Freedom Trail in Boston, Massachusetts

Elena Elisseeva

 

If you only have time to see a few of Boston's many historical landmarks, the Freedom Trail is your best bet. This 2.5-mile trail passes by some of America's most historically significant houses, churches, and burial grounds. Whether you take a guided tour or walk it on your own time, be sure to check out patriot Paul Revere's house, the Old North Church where the famous signal "One if by land, and two if by sea" was sent, and Bunker Hill, the site of the first major battle in the Revolutionary War. Finish off with a beer at America's oldest bar, the Bell in Hand Tavern.

9. Shove off to the Boston Harbor Islands

Boston Harbor Islands in Massachusetts SmarterMedium

Boston Harbor Islands in Massachusetts

SmarterMedium

 

You could spend days exploring the beaches and forests of the Boston Harbor Islands without even scratching the surface of all there is to see and do. The main draws are outdoor activities like swimming, camping, and hiking. There are also group yoga sessions on Saturdays during the summer at the Visitor Center on Spectacle Island. In addition, you can spot wildlife on the islands, like deer, fox, and muskrats, harbor seals, crabs, and clams. To get to the islands, hop on a ferry at the Long Wharf North Pier. We suggest Little Brewster Island to see America’s oldest light station; Bumpkin, Grape, Lovells and Peddocks for camping; and Spectacle Island or Lovells for great beaches.

Stephanie Mee

Stephanie Mee is a freelance writer and editor currently based in Bali, Indonesia. Her work has been featured in numerous magazines, newspapers, and websites, and she is constantly on a mission to seek out new stories and adventures. In addition to being an avid wordsmith, she is also an incurable foodie and wanderluster.

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