The 20 Coolest Urban Adventures in Boston

Published On 09/26/2016 Published On 09/26/2016
Albert Pego/Shutterstock
Michael Dwyer/AP Photo

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).  View on Map

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? View on Map


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. View on Map

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. View on Map

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. View on Map

Stephanie Rogers/Flickr

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. View on Map


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. View on Map

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. View on Map

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. View on Map

Boston Gondolas/Facebook

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. View on Map

Courtesy of Timberland
Robbie Shade/Flickr

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. View on Map


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. View on Map

Revolution Trapeze/Facebook

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. View on Map

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? View on Map

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. View on Map

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. View on Map

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. View on Map

Jason Eppink/Flickr

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. View on Map

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. View on Map

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. View on Map

The Boston Harbor Islands are a part of a large recreational area, perfect for swimming, fishing, camping, sailing, and almost every outdoor activity you can think of. The islands, Bumpkin, Grape, Lovells,...more

This 15-acre Greenway is a ribbon of Boston's contemporary parks, which house various art exhibitions, a carousel, and grassy areas on which to chill. Strolling down it will take you through a series of mu...more

This year-round alternative to sitting in traffic gets you to your destination via Boston Harbor, making your commute at least 10 times more enjoyable. Logan Airport is water taxi's most popular destinatio...more

William J. Devine is the second-oldest golf course in the country, and just so happens to sit on 70 acres, smack dab in the middle of Boston. So you can literally be one of those ballers who golf at lunch.

This kettle pond in the Jamaica Plain section of Boston is a part of the "Emerald Necklace" string of ponds and is restocked with fish every season. Naturally, that makes it an ideal fishing locale in the...more

This natural walkway is a secret until the tide is low. At that time, a sandbar appears and allows you to walk from Squantum to Thompson Island, where you can learn about the island's wildlife.

Hop on an authentic lobster boat and witness the entire fishing process from dropping traps to serving up your catch on these narrated private tours of Boston Harbor. You'll learn about the history of the...more

You may not associate stargazing with urban city life, but the Boston University Coit Observatory is open to the public for about an hour every Wednesday evening. You can find various constellations under...more

AdvenTours offers guided nighttime bike tours along Boston Harbor, offering some of the best sunset views of the waterfront in the city. Tours last about two hours and travel past Long Wharf and the Instit...more

An art museum and exhibition space, the Institute of Contemporary Art sits harborside in Boston. It was originally the Boston Museum of Modern art and built in 1936. Today, it showcases everything from pai...more

Ever wanted to try out one of those gondola rides with the guide dressed in a striped shirt and straw hat? Well, now you can, without shelling out for a plane ticket. Boston Gondola Tours offers the whole...more

Fenway Park
$ Fenway-Kenmore

Located in the heart of Boston's Kenmore Square, Fenway Park has been home to the Boston Red Sox (and the famous Green Monster) since 1912.

The Massachusetts State House is the capitol and the seat of the state government of Massachusetts. It houses the General Court as well as the offices of the governor.

This 217-year-old retired wooden-hulled frigate is a literal piece of history moored in Boston Harbor. It's the only wartime ship still afloat and promotes education about the navy's role in war through ou...more

Faneuil Hall Marketplace
$ Downtown Crossing

This historic, open air marketplace dates back to Boston's inception as one of the first cities in America. Catch live events in the public square, peruse local shops, and dine at established restaurants a...more

Probably one of the coolest experiences you can have in a library. The Mary B. Eddy Mapparium allows you to walk up three flights on the inside of a globe to see the world map from a completely different p...more

If you've ever wanted to learn how to do amazing Cirque du Soleil-level acrobatics, Revolution Trapeze in Watertown is your best bet. Here you'll learn all the ropes (no pun intended) involved in being an...more

The Warren Anatomical Museum, which is a part of the Harvard Medical School's Countway Library of Medicine, houses some of Harvard professor John Collins Warren's collection of strange and unusual anatomic...more

$ Back Bay

This Back Bay shoe store stocks the latest in style-y sneaks, but you'll have to find it (hint, a bodega is involved) before you get your hands on those limited-edition kicks.

Bogie's Place
$$ Downtown Crossing

Hidden behind a burgundy curtain in the back of JM Curley, Bogie's Place is a tiny speakeasy-style steakhouse with a cult following -- and most people only found it after entering the venue by mistake whil...more

JM Curley
Downtown Crossing

"Just don't be a douchebag," reads one of the etiquette guidelines on the wall at this hip Downtown Crossing eatery, setting the scene for its no-nonsense approach to enjoying yourself over brews and burge...more

This is one of Boston's picturesque secret gardens. Hidden atop a parking garage, the Cambridge Center Garden has walking paths, various types of flowers, and even lawn games.

Pick up a new hobby and head to this Port Norfolk winery where -- over the course of almost a year -- you'll go through the entire process of crafting your own fine wine, doing everything from de-stemming...more

If you live in the middle of Boston but really want to learn to be an avid mountain climber, look no further than Eastern Mountain Sports, where you'll learn all the tricks of the trade at Quincy Rock Quar...more

Helicopter rides! What could be more fun than that? Boston Helicopters offers you a bird's eye view tour of Boston, and, if you're feeling adventurous, piloting lessons.

If you're looking for a retreat from city life, Allandae Woods has everything you need to unwind in 86 acres: ponds, walking trails, and plenty of flora and fauna to admire.

Royale Boston
$$ Theatre Dist.

RB's a sleek Roman-esque nightclub/event venue (with over 100 live concerts a year), regally outfitted with plush gold leather couches and lion statues, balcony lounges, and a huge dance floor/stage.