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Top 10 Rooftop Bars and Restaurants in Boston

Boston is home to many atmospheric and delicious restaurants this amazing city has to offer. Throughout the summer in Boston, sometimes you may be so hungry to settle for a yummy meal at the closest outdoor seating and patio. However, if you are looking to elevate your summer restaurant experience, try out the numerous rooftop bars and restaurants sprinkled throughout the city. We have compiled a list of the top 10 rooftop eateries, from romantic hideaways to swanky hotspot rooftops. 


Cityside Tavern- 1960 Beacon St., Brighton

Cityside Tavern has been a hotspot for Boston College students and Brighton residents since ‘85. This restaurant is a friendly, yet classic tavern that is great for people watching. Their rooftop deck overlooks Cleveland Circle and the Green Line C trains. Enjoy your summer late morning with something from Cityside’s “Hangover Cures 101” menu of brunch cocktails, including a boozy iced coffee with peanut butter whisky and Reese’s Pieces candies.


The Colonnade Boston’s Rooftop Pool- 120 Huntington Ave., Boston 

The Colonnade Boston’s mega-popular rooftop bar and deck is the perfect spot on a hot day to enjoy one of their many fruity cocktails while taking a refreshing dip in their rooftop pool. Non-hotel guests are more than welcome to visit for $45 per guest fee, plus a $20 minimum on food and drink. If you are looking to spread out a little bit more, you and up to 6 of your friends can also reserve a cabana. The cabana’s are decked out with chaise lounges, a TV, and mini-fridge. 


Contessa- 1 Newbury St., Boston

Recently opened this June, Contessa is a Northern Italian-inspired restaurant located in the luxury and up-scale Newbury Boston Hotel. This new rooftop deck is facing the Public Garden, so you can enjoy your delicious meal with the beautiful views Boston is famous for. Contessa will also be open year round, it has enclosed the rooftop space with retractable glass panels and roofing, so it can serve as a four-season dining destination too.


Coppersmith- 40 W. 3rd St., South Boston

This Southie hotspot is not only home to the 75-seat “porch” in the front of their restaurant, but also a vintage Airstream turned rooftop bar, called the Airdeck. This multi-level rooftop bar and restaurant has summery cocktails, craft beer, barbecue plates, buffalo shrimp, sweet potato tots, and more.


Cunard Tavern- 24 Orleans St., East Boston

At Cunard Tavern, it feels like you are cocktailing on top of a shipping container, called the “TopDeck”. This rooftop bar and eatery overlooks East Boston and is the perfect spot to see a stunning summer sunset. It is only open Thursdays and Sundays and their deck is on the smaller side, so definitely reserve a table before you make your visit. 


Daedalus- 45.5 Mt. Auburn St., Cambridge Located right in Harvard Square, Daedalus is one of the oldest rooftop eateries in the Boston area. They have been in business and serving their crowd, primarily consisting of college grads, for 20 years now. Daedalus specializes in classic American food and drinks, from sangria to some dessert-friendly Scotch and ports.


Deck 12- 65 Seaport Blvd. (inside Yotel), Boston

Located about a dozen floors above one of Seaport’s famous and luxury hotels, Yotel. Yotel is a hotel that offers its guests a trendy, but budget-friendly experience with cruise-ship cabin-sized rooms. The small, but chic Deck 12 welcomes both non and hotel guests to relish their al fresco dinner, drinks, or weekend brunch. They are also open during the chillier months because of the many heaters they use.


Dorchester Brewing Company and M&M BBQ- 1250 Massachusetts Ave., Boston (Dorchester)

Dorchester Brewing Company recently added a beautiful exterior rooftop deck with open-air tables, offering remarkable views of the Boston city skyline. Their menu, from the in-house restaurant M&M BBQ, consists of a vast spectrum of house beers, chef-owner Geo Lambert’s famous ribs or the “Fenway” soft pretzel with smoked cheese sauce.


Earls Kitchen + Bar (Back Bay)- The Shops at the Prudential Center, 800 Boylston St., Boston (Back Bay)

This spacious, twinkling and light-strung rooftop deck seats more than 200 foodies, with both lounge and dining style seating. Earls Kitchen + Bar’s rooftop deck showcases a ginormous light-strung tree and ivy-lined walls.


Felipe’s Taqueria- 21 Brattle St., Cambridge

This casual Mexican spot has their delicious salt-rimmed margaritas flowing by the pitcher. Located right in Harvard Square, Felipe’s Taqueria’s menu specializes in burritos and Baja-style tacos filled with wood-grilled meats, fish, and veggies.