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The 20 Coolest Urban Adventures in Boston

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Greenway Art Walk

For our money the Greenway is the city’s most creative stretch. This 15-acre-long park takes you past a series of temporary art exhibitions commissioned by the city, from murals to giant sculptures, interactive installations, and seven different water fountains. Remember that the Harbor Fog Sculpture emits mist and (gentle) harbor noises whenever it detects human movement, (please, try not to scream -- it's embarrassing). 

The Harbor Islands

Urban camping isn’t just an urban legend. Hop on a ferry to four of the Harbor Islands -- Bumpkin, Grape, Lovells, and Peddocks -- and pitch a tent on a city archipelago (imagine telling campfire tales with the city skyline as your backdrop). Each island has grills, picnic tables, and hiking trails; Lovells also has a private swimming beach, and Peddocks even has yurts set up for the glamping set. Who needs that Cape traffic, anyway?

Water Taxi

If your Uber expenses are getting out of control, consider traveling by sea instead of land. The city’s year-round water taxis are still bizarrely underused, but their convenience is undeniable: just give a call and a boat will pick you up anywhere on the waterfront in about 10 minutes. Logan Airport is the most common destination, but you can also motor your way to East Boston, Charlestown, the North End, and spots all along the Seaport. Bonus: freshly tousled hair.

Golf in Franklin Park

1 Circuit Drive, Dorchester
What, you didn’t know an 18-hole course sits smack dab in the middle of the city? Not only that, but the William J. Devine Course is also the second-oldest public course in the country. The par-70 acre course gets high marks for its setting and staff service, never mind the well-maintained greens and picturesque ponds. And yup, there’s a clubhouse, complete with restaurant, bar, and outdoor seating; sometimes there’s even a grill set up at the end of the 6th hole. Just beware the dreaded course geese.
Elise Amendola/AP Photo

Jamaica Pond

507 Jamaicaway, Jamaica Plain
There’s lots of fishing to be found in the city, both saltwater and fresh. But Jamaica Pond restocks the pond with trout and salmon every season, so you’re that much more likely to land dinner. Cast your line from the shore or rent a rowboat to hook the elusive deep(er) water catch; just be sure to secure a permit first.

Squantum to Thompson Island Walk

Dorchester St., Squantum
This might be the coolest walk in the city, and only a very few attempt it -- or even know about it. When the tide is right (i.e. low), a sandbar appears that allows you to walk right from Quincy’s Squaw Rock to the private island, no ferry required. You’re best off going with a guide to learn about the island’s flora and fauna -- and to remind you to turn back again before the tide comes back in.


Want assurance that your crustacean really is the freshest there is? Hop aboard an authentic lobster boat for a private tour around Boston Harbor. Once you’ve heard about the region’s lobstering history, you get to haul up two real-life traps -- and every legal lobster contained inside is yours to keep. Drawn butter not included.

Coit Observatory

725 Commonwealth Ave.
City light pollution doesn’t make for great constellation-spotting and not everyone can afford a high-powered telescope. Not to worry: every Wednesday night, the Boston University Coit Observatory opens its door to the public for some rooftop stargazing. The viewing starts no later than 8:30pm and goes for about an hour as staff point out various celestial thrills. You might just regret registering for geology over astronomy freshman year.

Night Biking

103 Atlantic Ave.
Night biking is not for the feint of heart, but AdvenTours eases your mind with guided nocturnal tours through the city. You’ll spend up to two hours cruising along the waterfront, visiting spots like Long Wharf and the Institute of Contemporary Art, as the sun sets over the harbor. And of course, once you’ve exhausted your pedaling energies, you’ll have your choice of harborside restaurants to decamp at.

Gondola on the Charles River

Beacon St. and Arlington St. (on the Esplanade)
Still jellie of all those friends who did their semester abroad in Italy? You can do them one better: take a gondola ride without shelling out a lick of airfare. Boston Gondola Tours offers both day and evening  private trips with a gondolier pushing you along (striped shirts and straw hats included). BYOBing is encouraged; you can even hire a photographer to document your trip from pushoff to docking.
Courtesy of Timberland

You might think know the city like the back of your hand, but you can always find something new, unexpected, or plain weird (in the good way). Turn any moment into an adventure, and dress for it with Timberland.

Boston Helicopters

492 Sutton S. Gate 3, North Andover
Okay, so you have to travel out of town to fly back into town, but a downtown helicopter ride is so completely worth it. Imagine a private 45-minute ride over all your favorite sights: Fenway Park, the State House, the USS Constitution, and Faneuil Hall.  If the ocean beckons, you can opt for a combo tour that also takes you along the North Shore. And if you’re completely enamored of the experience, you can save up and  return for a sunset tour of the skyline -- or even sign up for helicopter pilot lessons.


200 Massachusetts Ave. (inside Mary Baker Eddy Library)
It’s like journeying to the center of the earth, minus all those prehistoric animals and pesky volcanoes. This three-story, stained-glass orb, built in the 1930s, lets you view world geography from the inside out as you stand on a suspended walkway gazing upwards. Be sure to play with the acoustics, too: The spherical ceiling amplifies your words in all sorts of funky ways.

Trapeze School Watertown

249 Waltham St,. Watertown
Ever harbored idle dreams about running away and joining the circus? Your next best bet is to become a trapeze artist for the afternoon. Watertown houses a bona fide trapeze school offering two-hour classes to acrobat neophytes. Don’t fret if you’re not getting the (literal) hang of it: the last half-hour is devoted solely to catching. There’s also an aerial arts program for the mildly height-adverse—think Cirque du Soleil with all those folks floating around in fabric.

Warren Anatomical Museum

10 Shattuck St.
When you’re looking for something a little more macabre than paintings or sculptures, head to the Warren Anatomical Museum for a survey of yesteryear medical practices. All the fascinating ephemera is here -- a kidney stone collection, Civil War-era medical equipment, the skeletal remains of conjoined twins, and the skull of Phineas Gage, i.e. the dude who survived an entire iron rod through his brain. Just maybe don’t eat lunch first?

Bodega Store

6 Clearway St.
Shoe-shopping is so much more exciting when it’s clandestine. Hidden behind an innocuous-seeming convenience store is Boston’s best sneaker shop, selling every limited-edition import you could ever hope to slip your feet into. There’s cool-kid clothing and cool-kid accessories, too, making back-to-school (well, work) shopping that much easier.

Secret Steaks at Bogie’s Place

25 Temple Place
A steakhouse speakeasy? How did we get so lucky? Tucked behind a burgundy curtain in the back of downtown bar JM Curley, Bogie’s Place is a tiny chophouse that does right by the classics. There’s old-style caviar service, throwback cocktails, a wedge salad, and a la carte steak cuts that come with bone marrow and foie gras butter. Time to pull out your zoot suit.

Cambridge Center Roof Garden

4 Cambridge Center, Cambridge
Not only does the city have its own secret garden, but it comes with a view. Perched atop a parking garage in Kendall Square, this particular garden includes well-manicured paths and tulips, trees, and rose bushes aplenty. Not that Mary Lennox would approve, but there’s a ping-pong table and cornhole, too, likely owing to the Google office next door.

Rock Climbing in Quincy Quarry

This used to be the place where local teenagers would risk injury and death by jumping 70ft into the black waters below. But the Big Dig took care of this dilemma, as dirt was trucked in from the site to fill in all the main quarries. What remains today is a public reservation that offers all sorts of rock-climbing opportunity, from beginning slopes to more advanced walls. If you’re not the kind of person who travels with his own cords and harnesses, hook up with Eastern Mountain Sports, which books climbing expeditions here.

City Winemaking

26 Ericksson St
Nope, you don’t have to own a home in the Florence countryside to fashion your own Chianti. Instead, you’ll just need a quick mode of transport to whisk you down to the Dorchester waterfront and the city’s only winery. Patience is a virtue, as you’ll see your own barrel of wine through to completion, from fall crushing through summer uncorking. You can also swing by for regular tastings and shop the winery’s house wines if you’re getting impatient.

Get Lost in Allandale Woods

7 Veterans of Foreign Wars Pkwy, Jamaica Plain
You don’t think of Hansel and Gretel as city kids, but once you head to Allandale Woods, you can totally picture them getting lost on the way back from Fenway Park. The 86-acre woods includes ponds, marshes, a historic home (NOT made from candy), and walking trails aplenty. You’ll also find the remains of a stone wall built as part of the New Deal, which stretches for more than a mile and demands you practice your balancing skills for a little while.
Meaghan Agnew is always up for an adventure, especially in her home city, which she’s never done exploring. Follow her endless discoveries on Twitter and Instagram at @meaghandeth.