A boutique hotel in Cambridge is where to find Cambridge’s coolest rooftop bar. Blue Owl—named for the mascot of Tootsie Roll Pops, whose manufacturer has a factory just down the street—is perched on top of 907 Main and boasts panoramic views of Central Square. The spacious place is open Wednesday through Saturday. It doesn’t take reservations so there’s occasionally a wait, which you can ride out at the ground-floor restaurant or patio bar. Upstairs, whether you get a seat inside or on the roof deck itself, you’ll find highly original food and drinks inspired by late-night snacks from around the world. Order up a snack like Popcorn with Thai-style green curry seasoning and sip a drink like Garden Party, featuring jasmine-infused Toki Whisky, honey, citrus and soda—and take in the sights. 

For a unique vantage point on the Boston beer scene, head to Dorchester Brewing Company. The taproom serves up a range of classic and creative beers, from Light Year Journey NEIPA to a fruited sour ale called Açaí Bowl; as well as hard seltzer, cider, wine, and boozy slushies. DBCo. also boasts a Rooftop Hopservatory, aka a glass-domed beer hall and open-air roof deck with Boston skyline views. It’s open every day—and so is awesome on-site restaurant M&M BBQ. Pair legendary ribs, a brisket sandwich, or one of our favorite Fried Chicken Sammies with the brews and the views. DBCo. takes large-party roof deck reservations, but note: M&M BBQ closes one or two hours earlier than the brewery, depending on the evening. 

The rooftop restaurant at The Newbury Hotel would be a destination no matter what, on account of its prime Back Bay location and Public Garden views. But Contessa really soars: This gorgeous gal pays homage to the grand villas of Northern Italy complete with colorful tiles, verdant trees, and glinting brass details. The Boston debut for New York City’s Major Food Group, Contessa is an ultimate scene, with wall-to-wall windows surrounding some of Boston’s hardest seats to score, but it’s worth the effort for an unparalleled setting. The menu is also evocative of Northern Italy, with rich pasta courses like Macaroni con Cinghiale (wild boar sauce) and spicy Shrimp Mezzaluna. Select a bottle of wine from the lengthy list or sample Contessa’s renditions of classic Italian cocktails and be part of the scene.

Before the Seaport was full of rooftop bars and places to be seen, there was Legal Sea Foods Harborside. First opened in 2011, this is a classy, three-level, waterfront version of the crowd-pleasing seafood restaurant. The top-floor rooftop lounge has a retractable glass ceiling and promenade patio with panoramic views of the Boston skyline, Fish Pier, and beyond. Heading up here for a glass of bubbles, Red Sangria, or a Gin and Tonic is a summer necessity in the Seaport, but the roof deck has a lively atmosphere year-round. The food menu is limited on the third floor, but you can order up some oysters and be very pleased with your choices. The Legal Harborside roof deck is open nightly and on weekend afternoons. 

Bustling Broadway never looked so good as it does from 14 stories up. High above South Boston, Six West affords breathtaking views of Southie, the South End, Dorchester, and downtown—not to mention summer sunsets. This seasonal rooftop lounge has a fairly slim food menu—think: Burrata with marinated sugar snap peas and garlic bread crumble; Lamb Meatballs with tzatziki and pickled shallots; a Maine Lobster Roll—but, considering the kitchen is quite a distance down, it’s an impressive (and delicious) array. Start the night here to catch the vibes with creative drinks like Green Monstah: a vibrant, spicy green-juice riff with ginger, lime, and Altos Tequila; or a Frozen Pineapple Daiquiri made with Plantation 3-Star Rum. Six West sits atop the Cambria Hotel, but it’s from the restaurant group behind South End cocktail den Wink & Nod. It’s open daily.

Chef Will Gilson of Puritan & Company has added several new East Cambridge restaurants in recent years, including The Lexington, an American brasserie featuring a rooftop bar and a patio. The second-story spot and its open-air promenade anchor the up-and-coming area of Cambridge Crossing. It’s on a similar level as the elevated train tracks rolling into nearby Lechmere, and while you can’t hear the Green Line barreling into the station, you can see the trains—and it’s pretty cute. Local residents and young professionals walk their dogs in the hilly, pondside park below. The Lexington has an impressive local beer list and selection of wines and cocktails, as well as creative comfort food like Onion Dip with potato waffles, trout roe, dill, and capers; and Roasted Cod with shrimp, peas, and herb broth. It’s open nightly with a full dinner menu, reservations, and room for walk-ins.

The Boston restaurant by Trillium Brewing Company is not your average taproom. The industrial-chic space in Fort Point spans two floors with ample seating and full service upstairs, plus an elevated menu of farm-to-table fare befitting some of the best beers money can buy. There’s also a roof deck for your pre- or post-meal enjoyment of drafts like Citra Free Rise Saison, Daily Serving fruited sour beers, and IPAs named for the surrounding streets. The drinks-only rooftop patio is open Friday through Sunday with its own bar and comfy couches for catching up with your crew. Put your name in for a table (there’s often a wait) and head up here for exceptional beer and views of the South Boston Seaport.

Take in the earthly delights of a meal at Terra from the rooftop lounge. The magical garden vibes of Eataly Boston’s third-floor restaurant continue on the attached patio, which is tucked in among skyscrapers in the Back Bay. Twinkling string lights and lush pots of white flowers accent the urban oasis. The menu brings out the best of the season, such as skewers of Pesce Spada, or grilled local swordfish with tomatoes and basil; and ricotta-filled Ravioli with zucchini blossoms and lemon butter. Match it all with beverages by turns botanical and fire-kissed, from Parsley Park, and herbal gin martini; to the Plum Palmetto, with plum-infused rum and smoked maple syrup.