The Most Exciting Rooftop Bars and Restaurants in Boston
Head to a sky-high cocktail bar in Back Bay, a brewery roof deck in Dorchester, or a swanky hot spot in South Boston.
Taking in the bird’s-eye panoramas at View Boston’s rooftop bar, Stratus. / Photo by Atlantic Pictures
Sometimes you’re fine with simply finding the closest possible restaurant patio for a pleasant al fresco meal. At other times, though, there’s something about ascending to a rooftop bar for a slightly more, well, elevated experience. When that mood strikes, here’s where to head, from a cocktail bar 51 floors above the city to beers and barbecue with skyline views to tasty tacos under clear blue skies.
This guide was last updated in August 2023; stay tuned for periodic updates.
Blue Owl. / Photo by John Bellenis
Blue Owl
A fantastic playlist—solid funk on one recent visit—and friendly staffers make this the perfect place for after-work drinks with your coworkers or a swanky date night later in the evening. This isn’t a well-drinks-in-plastic-cups sort of rooftop: It’s all about highly creative cocktails and mocktails—in actual glassware!—up here. Highlights include the Harvest Moon (pork-belly-fat-washed mezcal, succotash, and lime) and Dill or No Dill (dill aquavit, peppercorn sochu, cantaloupe, and lemon). The tasty mix of globally inspired snacks doesn’t hurt, nor does the view of Cambridge architecture and colorful sunsets. You’ll find cozy lounge seating and high-tops outside, and there’s a lovely indoor section with large windows, too, if the weather is uncooperative.
Sonder 907 Main, 907 Main St., Central Square, Cambridge, 617-349-2968, blueowlcentralsq.com.
Cityside Tavern
A popular watering hole for Boston College grad students and their Brighton neighbors since ’85, Cityside is a friendly, straightforward city tavern with great people-watching, thanks to its roof deck overlooking Cleveland Circle and the comings and goings of the Green Line’s C trains. Enjoy your anthropological studies with something from Cityside’s “Hangover Cures” menu of brunch cocktails, including a boozy iced coffee with peanut butter whiskey, chocolate whipped cream, and Reese’s Pieces candies.
1960 Beacon St., Cleveland Circle, Brighton, Boston, 617-566-1002, cityside-tavern.com.
Contessa. / Photo by Douglas Friedman
Contessa
You won’t be able to feel the summer breeze atop this rooftop—the space is fully enclosed—but you can’t beat the views of the Public Garden and Back Bay skyline at this glitzy Northern Italian-inspired restaurant in the Newbury Boston. It’s the first foray into Massachusetts from Major Food Group—a, well, major food group with two dozen swanky restaurants in major cities around the world. They’ve since opened a couple outposts of their casual red-saucy Parm brand in and near Boston, but Contessa remains the place to go for special-occasion dining and glamorous vibes (or a particularly fancy brunch). We’re partial to the squash carpaccio and the spicy lobster capellini.
The Newbury Boston, 3 Newbury St., Back Bay, Boston, thenewburyboston.com.
Cunard Tavern has a roof deck with East Boston waterfront views. / Photo by Brian Phillips Photography
Cunard Tavern
It feels like you’re cocktailing atop a shipping container at Cunard Tavern’s so-called Top Deck in East Boston, a great place to see a spring or summer sunset over the western horizon. Currently open every night but Monday (and featuring trivia on Tuesdays), the deck has slim square-footage—so reserve a table in advance if you want to soak up the wharf-side breezes while wolfing down short rib quesadillas with a craft brew.
24 Orleans St., East Boston, 617-567-7609, cunardtavern.com.
Daedalus
In Harvard Square, a neighborhood that has transformed dramatically over the last decade, enduring hangouts like the 22-year-old Daedalus take on a kind of mythic quality now. At this point, it has one of the oldest rooftop dining scenes in the area, still full of garrulous grad students who either sound like they’re on double dates or as though they’re practicing for debate club. In all instances, the people-pleasing New American food and drink, from sangria to some dessert-friendly Scotch and ports, remains a reliable social lubricant.
45.5 Mt. Auburn St., Harvard Square, Cambridge, 617-349-0071, daedalusrestaurantcambridge.com.
Deck 12 at Yotel. / Courtesy photo
Deck 12
You’ll want to book a reservation in advance for this little nook a dozen floors high in the sky at the Seaport’s Yotel—and bring sunscreen, as it’s mostly uncovered, aside from a couple of umbrellas. Twinkling string lights add a bit of magic after sunset, but the spot is also a favorite for brunch—hello, waffle burgers. Views are impressive closeups of the Financial District skyline, and there’s plenty to drink. Start with the house frosé and then dip into other warm-weather concoctions, such as a passion-fruit mojito or a pineapple-infused bourbon-and-black-tea cocktail. A concise selection of wine and beer is available, too (nothing wrong with a Del’s Summer Shandy on a sunny rooftop!). Keep it in mind for the cooler months, too, when Deck 12 breaks out the heaters and a ski lodge theme.
Yotel Boston, 65 Seaport Blvd., Seaport District, Boston, 617-377-4747, deck12bos.com.
The rooftop beer hall at Dorchester Brewing Company is ready for year-round enjoyment. / Courtesy photo
Dorchester Brewing Company
The upper level of this neighborhood fave features a year-round enclosed space—with greenhouse-style floor-to-ceiling windows for views regardless of the weather—and a lively seasonal outdoor deck. (Look past the parking lot for impressive Back Bay skyline vistas.) Friendly crowds gather in the sun to enjoy ribs and brisket from the on-site restaurant, M & M BBQ, and, of course, beer. Dorchester Brewing’s own beers are on tap in numerous styles—fruited sours, New England IPAs, saisons, and more—plus other options produced on-site by partner brewers. There’s a bit of cider and wine, too.
1250 Massachusetts Ave., Dorchester, Boston, 617-514-0900, dorchesterbrewing.com.
Earls rooftop. / Photo by Melissa Ostrow Photography
Earls Kitchen & Bar
This twinkling roof deck seats more than 200 people across various dining and lounge-style settings. It has a gigantic tree and an ivy-lined wall, and the retractable roof allows for three-season enjoyment. Earls, a Canadian chain, offers a globe-trotting menu, so you can enjoy Yucatan chicken tacos while your date digs into yuzu tuna tataki. Add a frozen margarita for fun.
The Shops at the Prudential Center, 800 Boylston St., Back Bay, Boston, 857-957-0949, earlsrestaurants.com.
Felipe’s Taqueria
It’s party central at this iconic Harvard Square rooftop. There’s some seating, but you’re going to want to be on your feet, shoulder to shoulder with friends and strangers, socializing with the young, energetic crowd. The views are of good old Harvard Square—lots of red bricks!—and you’re almost definitely drinking a frozen margarita or a Modelo, perfect complements to burritos and Baja-style tacos filled with wood-grilled meats, fish, and veggies.
21 Brattle St., Harvard Square, Cambridge, 617-354-9944, felipesboston.com.
Gordon Ramsay Burger
Donkeys, assemble: The particularly loud television personality and restaurateur Gordon Ramsay opened his second Boston spot in summer 2023, this one focused on burgers. The second floor features a partially covered but mostly sunny roof deck with downtown and Greenway views—a good setting for an Oreo crème brûlée milkshake, some truffle fries, and a hefty burger.
Canopy by Hilton Hotel, 99 Blackstone St., Downtown Boston, 617-263-8610, gordonramsayrestaurants.com.
Legal Harborside. / Photo by Chip Nestor
Legal Harborside
This three-story behemoth is a stunner in all seasons, but summertime is when it really excels. Grab a pint at nearby Harpoon before hitting up Legal’s picturesque rooftop patio—equipped with a rain-fortified retractable roof—for some steamers, New England fried clams, and freshly shucked shellfish.
270 Northern Ave., Seaport District, Boston, 617-477-2900, legalseafoods.com.
The Lexington
Chef Will Gilson’s triad of restaurants at Cambridge Crossing includes Cafe Beatrice, an all-day café; Geppetto, a full-service Italian spot; and the Lexington, a people-pleasing restaurant and bar that just happens to boast a rare-for-the-neighborhood roof deck connected to its dining room by wide walls of retractable windows. It’s a stylish, breezy space for kicking back with Gilson’s New American cuisine (try the French onion grilled cheese or pan-seared salmon) and delightful cocktails.
100 N First St., East Cambridge, 617-945-1349, thelexingtoncx.com.
Lookout Rooftop and Bar. / Courtesy photo
Lookout Rooftop and Bar
Perhaps best known for its winter igloos, the Envoy Hotel’s rooftop is a destination in warmer months, too, drawing huge, well-dressed crowds to sip cocktails high above the Seaport. Special seating areas, including some with fire pits for those summer nights that get a little chilly, can be reserved for a fee. Wherever you sit, the downtown skyline and Boston Harbor are in full, glorious view. Expect easy-drinking cocktails like berry frosé and a bee’s knees variation; classic cocktails with a choice of top-shelf liquors; and straightforward beer and wine lists.
The Envoy Hotel, 70 Sleeper St., Seaport District, Boston, 617-530-1538, theenvoyhotel.com.
Mex Taqueria & Bar. / Courtesy photo
Mex Taqueria & Bar
Ascend through the first two levels of this gorgeously designed restaurant to find the rooftop, a festive hideaway above Kendall Square featuring hospitable service and tacos aplenty. A retractable covering provides a bit of shade on part of the roof, but be prepared for sun. (There’s not much to see up here aside from a building across the street and plenty of blue skies above, but fun vibes make up for the lack of a spectacular view.) To drink, you’re ordering margaritas galore, in plenty of flavors, of course, but don’t miss the mangonada slushie, garnished with a Tajín rim and tamarind candy stick. And don’t hesitate to come here for a full meal: The tacos are top-notch.
500 Technology Square, Kendall Square, Cambridge, 617-945-2503, mexcambridge.com.
Over the Charles. / Courtesy photo
Over the Charles
With a relaxed atmosphere, this rooftop on the 16th floor of the DoubleTree Suites by Hilton Boston-Cambridge plays host to hotel guests and locals alike, who come for the stunning vistas and satisfying bites and drinks. Framingham-based Jack’s Abby, known for its lagers, is featured here; watch for a rotating selection on draft as well as some options by the can. There are also plenty of cocktails, including a couple of selections available by the five-serving tower. Bonus points for the excellent chocolate-chip-cookie ice cream sandwich. High-top seating ensures you won’t miss a thing when it comes to the commanding panoramas of the Charles River—and the skyline—on both sides.
DoubleTree Suites by Hilton, 400 Soldiers Field Rd., Allston, Boston, 617-783-0090, hilton.com.
Pier 6. / Photo by Brian Samuels Photography
Pier 6
Dine in full view of the historic Charlestown Navy Yard and the USS Constitution on the roof deck, or on the huge, first-floor patio. Downstairs, there’s an outdoor bar, with rosé magnums and cocktails like the painkillers and frozen mudslides. Plus: There’s a complimentary (weather-dependent) seasonal water taxi directly to the equally scenic East Boston sibling spot, ReelHouse.
1 8th St., Charlestown, Boston, 617-337-0054, pier6boston.com.
Rooftop at Revere
The Revere Hotel’s expansive rooftop bar offers the perfect blend of right-in-the-middle-of-the-city energy and up-so-high exclusivity. Settle in and enjoy the views; there’s a bit of a parking garage from one angle, but it barely detracts from the downtown city sights and gorgeous sunsets. A mix of high-tops, standard tables, and bar seating give plenty of options for hanging out (plus, there’s some indoor lounge space to duck into if the weather turns.) You’ll find sangria, spritzes, and other refreshing, fruity cocktails available alongside a short beer and wine list—with a couple of pricier bubbly options if you’re feeling fancy—and a snacky food menu with nachos, tuna tartare, jerk chicken wings, and more.
200 Stuart St., Bay Village, Boston, 617-482-1800, rooftopatrevere.com.
The RTP at the Colonnade Hotel. / Courtesy photo
RTP at the Colonnade Hotel
It’s exclusive, it’s sunny, and it’s a must-visit on your summer-in-Boston bucket list. This isn’t just a bar a dozen floors above Back Bay with the skyline so close you could almost touch it: RTP stands for rooftop pool, and it’s among the only ones open to the public around Boston these days. (You’ll have to pay a hefty entrance fee if you’re not a hotel guest, though.) To drink, frozen cocktails like a peanut-butter mudslide and a fruity rum concoction take center stage, but you can dive into a non-frozen cocktail or a short list of beers and wines if you prefer.
The Colonnade Hotel, 120 Huntington Ave., Back Bay, Boston, 617-424-7000, colonnadehotel.com/roof-top-pool.
Samuel Adams Downtown Boston Taproom. / Photo by After Brunch Entertainment x Sam Adams Downtown Taproom
Samuel Adams Downtown Boston Taproom
Drinking Sam Adams right outside Faneuil Hall might feel a tad touristy, but that’s not a bad thing when you’re soaking in the sunshine and knocking back a lager after work in this umbrella-bedecked space. And the roof deck is just a story up, so it’s perfect for those who feel a little queasy at the thought of bird’s-eye views. (Instead, the view is basically Boston history—including, conveniently, a Samuel Adams statue that long predates the opening of the taproom.) To drink, choose from 20 or so rotating Sam Adams brews—everything from classics such as the Summer Ale to taproom exclusives like Midnight Marauder, a black IPA, and Land of the Goths, a Swedish farmhouse ale. Flights are available, too, as are snacks like pretzels and tater tots.
60 State St., Downtown Boston, 617-466-6418, samadamsbostontaproom.com.
An espresso martini at Six\West. / Photo by Rachel Leah Blumenthal
Six\West
Fourteen stories up at Southie’s Cambria Hotel, the Six\West rooftop has a relaxed ambiance with plenty of room to breathe, thanks to reservations-recommended seated service across a mix of bar space, high-tops, standard tables, and lounge furniture. Look for the giant Jenga set if you’re in a playful mood. The views are a little industrial in the foreground, with a rail yard and the expressway as the prominent landmarks. But look farther for a clear view of the South End and Back Bay skyline. Enjoy it while you drink no-frills margaritas and mules with a choice of fruity syrups (think passion-fruit-pineapple and mango-lime-habanero), plus other summery cocktails, a bit of wine, and a largely local beer list. There’s a light food menu, too, with salads, flatbreads, and such.
6 W Broadway, South Boston, 413-324-9518, sixwestbroad.com.
The views from Stratus at View Boston. / Photo by Rachel Leah Blumenthal
Stratus at View Boston
You’re on top of the world—or at least the Greater Boston area—51 floors up at the rooftop cocktail bar at View Boston, the Prudential Center’s recently reimagined observatory space. You’ll need to buy a ticket to get in; start your visit on floor 52, with giant windows providing stunning views all around. From there, you can descend to Stratus to relax with a drink in the open air, taking in endless sights (and taking endless selfies). The 360-degree views include…pretty much everything. Interactive digital displays and models on the 52nd floor will help you spot landmarks such as Fenway Park and the Museum of Fine Arts. Once you get to Stratus, look for a short and sweet list of cocktails, pitchers of sangria, and cans of beer, hard seltzer, and hard kombucha.
View Boston, the Shops at the Prudential Center, 800 Boylston St., Back Bay, Boston, viewboston.com/stratus.
Trillium Brewing Company’s Seaport roof deck. / Courtesy photo
Trillium Brewing Company
Trillium’s energy-packed Seaport location is topped with an uncovered roof deck with its own bar, open Friday to Sunday when weather permits. The space fills up fast, but if you’re lucky, you’ll be able to grab a table or room at the standing rail. Place your order at the bar and enjoy your drink among a pretty chill crowd of beer lovers. Trillium’s own beer is showcased here, naturally. The roof deck features a variety of rotating draft pours; keep an eye out for hoppy IPAs, a fruity Berliner Weisse or two, some crisp lagers, and more, not to mention hard seltzers from Trillium’s in-house brand, Soak. Views include Seaport architecture, old and new; the occasional low-flying gull; and Trader Joe’s—brainstorm your shopping list while you drink.
50 Thomson Pl., Seaport District, Boston, 857-449-0083, trilliumbrewing.com.
Umbria
Taking over the former Ristorante Fiore space, restaurateur Frank DePasquale debuted Umbria in summer 2023, a North End rebirth of a multi-story restaurant, bar, and club downtown that closed a few years back. The Italian steakhouse features two floors of indoor dining, plus a roof deck, Mia, which is set to open in early August—stay tuned for more details. (It’ll have a separate reservation system from Umbria and will be open until 1 a.m. daily.)
250 Hanover St., North End, Boston, 617-865-1265, umbrianorthend.com.
A version of this guide appeared in the print edition of the August 2023 issue with the headline “Through the Roof.”
