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Grabbing drinks on a sidewalk patio is delightful, but sipping sangria while taking in a sunset view from 10 stories up? We’ll choose the latter, thanks.
While Boston might not be a hub of rooftop drinking and dining, the city does offer some excellent options, whether on top of a Seaport hotel or at a waterfront restaurant in Charlestown. Below, we’ve put together a list of Boston-area rooftop bars and restaurants that are prime for an al fresco outing.
Perched atop 907 Main, a boutique hotel in Cambridge’s Central Square, Blue Owl debuted in September with a lengthy list of contemporary cocktails and international street food snacks. Guests have both an indoor bar and outdoor patio to choose from: The former is a sleek, modern setup sporting spacious booths and a smattering of tables, while the latter offers lounge chairs and high tops overlooking the square below. Try one of the bar’s signature drinks, the Pale Blue Owl, paired with Korean fried chicken wings, shrimp tika, and flautas. (907 Main St., Cambridge)
With windows that look out onto the Public Garden, Boston Common, and Newbury Street, The Newbury Boston’s rooftop restaurant and bar, Contessa, has some of the most dazzling views in the city. Retractable panels transform the space into an open-air eatery, and a lush plant collection helps bring the outdoors inside. With Major Food Group at the helm, guests can dine on Northern Italian fare (think tortellini en brodo and dry-aged Florentine steak) and sink into velvet banquettes with a martini or classic Italian spritz. (1 Newbury St., Boston)
Head to the upper deck of this popular Southie restaurant, where spaced-out tables and hanging lights provide a dreamy gathering spot. Weekend brunch features shakshuka, French toast, and egg sandwiches, while a drink menu includes cold beers, wine, and cocktails. Going with a group? Order margaritas and sangria by the pitcher, which serves up to six people. (40 W. Third St., Boston)
Located in the Jeffries Point neighborhood of East Boston, Cunard Tavern has expanded its outdoor seating options with sidewalk seating. But if you’re looking for a rooftop breeze, make a beeline for the top deck bar, where you can load up on bacon-wrapped dates, oysters, and fish tacos, plus beer, wine, and cocktails. Note: The rooftop deck is only open Thursdays through Sundays from 4 to 10 p.m. (24 Orleans St., Boston)
Find your way up to the roof deck of this Harvard Square restaurant, where lights twinkle at night and plenty of umbrellas provide shade on sunny days. Open for dinner only, the restaurant serves burgers, fish and chips, pastas, and quinoa bowls, while cocktails run the gamut from Moscow Mules to Mai Tais. (45 1/2 Mt. Auburn St., Cambridge)
Formerly known as Sky Lounge, Deck 12 offers Seaport views from Yotel’s rooftop, where you’ll find plenty of comfortable seating and an internationally-influenced food and drink menu. On weekends, diners flock here for brunch (think quiche, carne asada hash, and shakshuka), while evening meetups attract dates and groups looking for beer, wine, and cocktails — the “Slush du jour” makes for a cool libation on a hot summer day. (65 Seaport Blvd., Boston)
After a major renovation in 2019, Dorchester Brewing Co. emerged with a phenomenal rooftop patio. Not only can guests enjoy a solid lineup of beer, but M&M BBQ, the brewery’s in-house restaurant, offers some truly top-notch barbecue. The move: Pair a Galaxy Lights IPA with a plate of ribs and side of coleslaw. (1250 Massachusetts Ave., Boston)
Have a hankering for Mexican food enjoyed al fresco? Make a beeline for Felipe’s in Harvard Square, where you can get your fill of tacos, quesadillas, burritos, and churros on the restaurant’s rooftop deck. Pair your meal with a frosty margarita or a refreshing horchata. Felipe’s doesn’t take reservations, so you may need to wait in line for a spell. (21 Brattle St., Cambridge)
Legal’s third-floor promenade deck features a retractable roof and walls, making for a breezy, sunlight-filled space to sip wine while looking out onto the harbor. The top floor’s menu is more concise, comprised of shareable plates, sushi, and sashimi, but the beverage menu boasts dozens of wine by the glass, plus cocktails and pitchers of punch. (270 Northern Ave., Boston)
The Envoy Hotel’s rooftop bar is a prime spot for taking in waterfront views with friends or a date. Open for brunch, lunch, and dinner, Lookout serves classic bar fare — think burgers, truffle parmesan fries, and chicken thighs — alongside a concise cocktail, beer, and wine menu. Sunset views with a glass of wine? Sounds like a solid Friday night. (70 Sleeper St., Boston)
Charlestown’s Pier 6 boasts a rooftop deck right on the water, where guests can tuck into shrimp cocktail and lobster rolls while watching boats taxi across the harbor. Local craft beers are on tap, along with wine, frozen cocktails, and concoctions like the Pier 6 Sunset, made with bourbon, vermouth, lemon juice, simple syrup, and ginger beer. (1 8th St., Boston)
A rooftop patio in the North End? We’ll take it. Downstairs, Ristorante Fiore is all white tablecloths and carefully folded napkins, while upstairs, a rooftop deck lends a more casual atmosphere for twirling homemade spaghetti and sipping wine. (250 Hanover St., Boston)
Overlooking downtown Boston, this hotel lounge is one of the largest rooftop bars in the city, with more than 16,000 square feet of space. Take a seat at the bar’s high top tables, comfy sofas, or lounge chairs with a bourbon-based Saratoga cocktail or vodka-infused Secret Garden. To eat, the bar offers snacks like guacamole and chips and chicken thighs, as well as larger items like lobster rolls and skirt steaks. Finish off with some churros for dessert. (200 Stuart St., Boston)
Located near Faneuil Hall, the newest taproom from Sam Adams is in a decidedly more tourist-driven spot than its original Jamaica Plain location. Escape the crowds by heading to its roof deck, which overlooks a statue of the brewery’s namesake. Seating is first come, first served. (60 State St., Boston)
This rooftop bar atop the Cambria Hotel Boston in Southie sports stunning views of the city and, if you’re lucky, a panoramic sunset. Open for brunch, lunch, and dinner, the menu offers classic dishes including steak frites, pizza, and French toast, plus shareable plates of fried calamari, tuna tartare, and baked goat cheese dip. To drink, a Sixpresso martini made with coffee cordial and cold brew will provide a proper caffeine jolt. (6 W. Broadway, Boston)
If you’re heading to the rooftop at The Colonnade, it’s likely to use the hotel’s pool. (And rightfully so! It’s a good one.) But while you’re there, hit up The Colonnade’s rooftop bar, where you can sip on spicy strawberry margaritas, mocha mudslides, and red and white sangrias. Hungry? The kitchen also offers a poolside menu that includes turkey wraps, burgers, chicken tenders, and oysters. Hotel members can access the rooftop bar and pool for free, but non-members must pay $50 and make a reservation no more than 48 hours in advance by calling 617-425-3408. (120 Huntington Ave., Boston)
Located within the newly developed Cambridge Crossing complex in East Cambridge, The Lexington houses one of the neighborhood’s rare roof decks, with seasonal outdoor seating that looks out onto The Common. After snagging a seat, we highly recommend digging into the onion dip and potato waffle chips, seared scallops, and beer-battered fish tacos. Pair with The CX Common, made with gin, cucumber, mint, and dry vermouth. (100 N. First St., Cambridge)
The Seaport branch of Trillium offers a small but mighty rooftop deck, perfect for people-watching while enjoying the brewery’s rotating draft selection. For noshing, Trillium makes a mean fried chicken sandwich, as well as smashed fingerling potatoes, grain bowls, and tuna poke. (50 Thomson Place, Boston)
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