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The Colonnade
Photograph: Courtesy The Colonnade The Colonnade’s rooftop pool and bar

The best Boston rooftop bars you need to know about

Hip hotels, neighborhood hangouts and waterfront decks; these Boston rooftop bars deliver views with a side of booze

By Eric Grossman and Time Out Boston Staff

Good weather means good moods, and when New England’s notoriously fickle weather allows, locals head out to revel in alfresco options including hikes, beaches, and parks. Boston has plenty of options for outdoor dining and drinking, from the best outdoor bars to the best waterfront restaurants. If you’re up for taking your fun to a higher level, check out our list of the best rooftop bars in Boston where you can get a drink and a great view of the city. When you’re ready to come out of hibernation and catch some rays, here’s where to go.

RECOMMENDED: Full guide to the best bars in Boston

Best rooftop bars in Boston

Lookout Rooftop
Photograph: Courtesy Lookout Rooftop

1. Lookout Rooftop and Bar

Bars Hotel bars Seaport District

Majestically perched atop the Seaport’s Envoy Hotel, this expansive, eighth-floor spot places a premium on luxurious comfort, with stylish lounge seating and upscale cocktails. The skyline and sunset views alone are worth the inevitable lines. Inside tip: Expect to wait a bit when visiting after work or before a concert at the nearby Rockland Trust Bank Pavilion.

Photograph: Courtesy Rooftop@Revere

2. Rooftop@Revere

Bars Hotel bars Bay Village

This Theater District hotel boasts one of the liveliest rooftop scenes in the city, with an amalgam of stylishly dressed staff and guests, and a smorgasbord of tropical drinks and shareable munchies. Lounge on a reserved couch or chill by the indoor, glass-enclosed pool and take in the 270-degree views from this seventh-floor perch. Psst: If you’re not down for purchasing a day pass, the rooftop is free and open to all after 5pm.

Legal Harborside 3rd Floor
Photograph: Courtesy Legal Harborside/Chip Nestor

3. Legal Harborside

Restaurants Seafood Seaport District

When you want to show off one of the city’s most dynamic neighborhoods to an outsider, take them to Legal Harborside’s roof deck. The plush lounge seating is a serious upgrade to run-of-the-mill patio seats, and the spectacular harbor views impress. Work your way through the extensive wine list and seafood-focused menu; sparkling rosé and oysters are always a wise choice.

Dorchester Brewing Co.
Photograph: Courtesy Dorchester Brewing Co.

4. Dorchester Brewing Co.

Bars Breweries Dorchester

Dorchester Brewing's taproom features Dorchester’s freshest brews—IPAs, porters, cream ales—alongside their latest collaborations. M&M BBQ provides amazing barbecue. The brewery now features the Hopservatory, an all-season rooftop greenhouse with city views, a game room, restaurant, and more taproom space with expanded offerings such as cider and wine.

Photograph: Courtesy YOTEL

5. Sky Lounge at YOTEL Boston

Hotels Seaport District

YOTEL Boston offers a year-round rooftop terrace with panoramic views of the city from its perch in the Seaport District. During the winter, guests feel like they're at a ski resort thanks to heaters, plush blankets, and purple hot water bottles. When the weather is warm, area workers and residents fill the terrace to catch some rays. Friendly staffers and fine food and drink complete the experience.

Trillium Brewing Company
Photograph: Courtesy Trillium Brewing Company

6. Trillium Brewing Company - Fort Point

Bars Breweries Seaport District

Trillium’s brews are among the most highly-prized and hardest to find in the area. Fortunately, Trillium's spacious Fort Point location offers beers brewed on-site as well as a full-service restaurant featuring New England farmhouse fare. The multi-level building has a taproom and dining area, and you can take it outside to the roof terrace and outdoor patio.

The Colonnade
Photograph: Courtesy The Colonnade

7. Colonnade Hotel

Hotels Boutique hotels Back Bay

Home to one of the city’s most famous rooftop hangouts, this Back Bay hotel has revamped its 12th-floor pool deck numerous times over the years. A mix of hotel guests and local scenesters rub lotion-covered shoulders while cooling off during Boston’s summer months. Private cabanas cater to the truly indulgent, while most patrons head to the bar to order a frozen cocktail alongside swordfish tacos or a lobster roll. Closed to the public on weekends, the rooftop is open to non-hotel guests (for a fee) on weekdays.

Sam Adams Faneuil Hall
Photograph: Courtesy Samuel Adams

8. Sam Adams Faneuil Hall Tap Room

Bars Breweries Government Center

Sam Adams Brewing's newest tap room is located just steps away from the Sam Adams statue at Faneuil Hall. The 15,000 square foot tap rooms is 3 levels, including an outdoor rooftop deck with views. Rotating taps feature the best brews, and #RandallThursdays feature innovative new drafts available on that day only. Stop by for Cheesy Hour on Wednesdays when you can try a flight of four "R&D" beers only available in Boston, plus four paired artisanal cheeses.

Pier 6
Courtesy Yelp/Pier 6

9. Pier 6

Restaurants Seafood Charlestown

Located on a marina in the Navy Yard, Charlestown’s most popular outdoor drinking and dining spot provides intimate views of Old Ironsides. A colorful mix of locals gaze out on to the city's skyline while nibbling on selections from a crowd-pleasing, seafood-heavy menu (e.g. Point Judith calamari, seared scallops). A well-stocked bar is on hand to help patrons imagine they're on the Cape.

Photograph: Courtesy Creative Commons/Flickr/Sarah Ross

10. Daedalus

Restaurants Contemporary American Harvard Sq

Housed in a former greenhouse on the outskirts of Harvard Square, Daedalus has been a longtime favorite of Cantabrigians seeking open-air environs. The roof deck is serene and spacious, a perfect spot for after-work drinks or a hangover-curing brunch. Large umbrellas protect the sun-averse, while ceiling fans cool down the covered tables; flower boxes add a bit of color to the mix. A solid beer and cocktail list combined with a (normally) calm crowd adds up to a dependable standby.

Felipe's Taqueria rooftop
Photograph: Courtesy Yelp/Neechi M.

11. Felipe’s Taqueria

Restaurants Mexican Harvard Sq

Felipe’s in Harvard Square is almost always packed, and for good reason: fresh, authentic, and fast Mexican fare. In the summer, the roof deck attracts even more fans, where you can enjoy fresh-squeezed key lime margaritas, nachos, and a cool breeze.

Ristorante Fiore
Photograph: Courtesy Ristorante Fiore

12. Ristorante Fiore

Restaurants Italian North End

An old-school haunt in the heart of the North End, Fiore’s rooftop bar feels like a European café crossed with a small sports bar, with wrought-iron seating and an exposed-brick bar. Over at the sit-down tables, an enormous wine list joins forces with a classic Italian menu, though, in our opinion, a glass of prosecco and a margherita pizza are all you need to complement the breezy atmosphere.

Courtesy Yelp/Cristina R.

13. Coppersmith

Restaurants Contemporary American South Boston

Outfitted with a vintage Airstream trailer-turned-bar on its roof desk, this 3,000-square-foot Southie behemoth packs a youthful crowd onto its rustic picnic tables. An assortment of globally-minded comfort fare and flavorful, straight-from-the-smoker barbecue satiaties the masses, while local craft brews keep the hops-heads happy. When there's a big game, just about everyone ducks inside to follow the action on a pair of 160-inch projector screens.

Sinclair rooftop
Photograph: Courtesy Yelp/Sam H.

14. The Sinclair

Music Music venues Harvard Sq

This Harvard Square music hall, booking nationally-renowned musicians nightly, is a classier option among music venues in the area. It even has a restaurant serving elevated American comfort fare. The restaurant's rooftop terrace is perfect for a pre-show cocktail.

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