The Most Essential Rooftop Bars in Boston
Drinks just taste better with a view.
The summer of 2020 has been all about the staycation: backyard grilling, exploratory walks, and modified alfresco dining. Oh, and of course, drinking under the sun. Enter the city’s rooftop bars, which began reopening with new safety protocols and are now here to bring you fresh breezes, dampened city noises, and manageable crowds. And don’t fret if you feel like your sky-high imbibing time is limited -- we have a sneaking feeling that New England summer is going to stretch as far as possible into fall this year. Make the most of it with some of the best rooftop bars in Boston.
The same weekend that outdoor restaurants began reopening, we drove through Southie and saw a huge line outside Six West. And we get it. The city’s newest roof deck entry atop Cambria Hotel Boston offers truly stunning sunset views and a chichi vibe. Pretend you’ve traveled to South Beach by ordering a frozen pineapple daiquiri and digging into a small-plates menu of truffled chicken nuggets and grass-fed beef sliders. Your time up top is limited to two hours; make a reservation ahead of time via Resy.
Last year, a good thing got a lot better. Quincy’s favorite roof bar got a major offseason overhaul -- think 5,000 square feet of alfresco space, an herb and produce garden, apple and pear trees, a sushi bar, and an outdoor kitchen serving roof deck-only dishes. Perhaps the best feature? A louvered roof system that can block out any pesky summer showers. No reservations are taken ahead of time, so it’s first-come, first-served.
Once upon a time, this beloved Southie gastropub was headed for the chopping block. But reports of its demise were greatly exaggerated, and today its upper deck is a welcome haven, with its hanging lights, well-spaced table, and epic brunch menu. And yes, its to-go “adult Capri Suns” are still available, the better to keep the party going when you leave. While reservations aren’t required, you’re best served by making one on OpenTable.
Cunard Tavern’s menu made a justified splash when the restaurant debuted in 2017 (gourmet dining in Eastie!), but it was the Top Deck that drove people into a joyful frenzy (an epic roof deck in Eastie!). With gorgeous skyline and water views, a walk-up window bar slinging cocktails and brews on tap, and a snack menu of street food bites, it’s a no-brainer for a precious night out. Reservations are required for a 90-minute visit, and parties are limited to six people. But keep the party going by ordering a couple of cocktails to go.
Those of us in the know can only marvel at how a good thing got so, so much better. Last year, the beloved Dorchester brewery underwent a massive extension and added a second-floor greenhouse and wraparound patio to its industrial facility. The spacious deck offers a stunning skyline view and even more space to drink some locally made brews (or wine! another upgrade!), and eat barbecue from the in-house M&M Ribs, located downstairs. Make a patio reservation or check the capacity counter on the website before risking a walk-in visit.
For those in Fort Point who love roof decks but seek a mellower scene, Trillium might be your answer. The third-floor, 65-person space is a favorite neighborhood alfresco hot spot, with its lounge seating and full bar serving all of Trillium’s latest offerings. And while there may not be water views, there are oysters -- a selection of items from the main restaurant menu are available upstairs as well. Reservations are required and can be made the same day starting at 9 a.m. (Visits are limited to 90 minutes, and party sizes max out at six people.)
The deck formerly known as Sky Lounge might not be able to offer its full lineup of summer programming this year (we sincerely miss the morning meditation), but the stunning 12th floor water views, twinkly lights, and comfy seating are still strong draws. Add in divine house cocktails and snacks like lobster avocado toast and Wellfleet clams, and you’ll almost feel human for the afternoon. You can make a reservation ahead of time by calling 617-377-4747 or sending an email to firstname.lastname@example.org.
There’s a little bit of paradise seven stories above the Theatre District at Revere’s rooftop hideaway. The 16,000-square-foot space is an elevated oasis of lounge seating, luxe cabanas, shaded swimming, and people-watching that can quickly devolve into gawking -- even in the summer of Covid.
The stunning rooftop pool at The Colonnade is like heading to a tropical location without ever leaving Back Bay. Curtained cabanas and wicker lounge chairs line the deck, all the better to enjoy seasonal cocktails, rotating craft brews, and some light fare for poolside snacking. To help cool you down while still keeping you safe, The Colonnade has instituted a strict set of COVID-19 protocols, including reducing roof deck capacity to below 50 percent, temperature checks, and masks when not in a lounge chair. Entrance will cost you $45, and reservations required by calling 617-425-3408 no more than 48 hours in advance.
When this eighth-floor space opened a few years ago, the competition to nab entry was downright fierce. We’re talking Boston Harbor and skyline views, many a refreshing cocktail made with locally produced spirits (including several large-format cocktails), and an exclusive-yet-chill vibe. An additional renovation a couple of years ago netted us 2,500 additional square feet. The deck is now open Thursdays through Sundays, and reservations are required and can be made on the site.
If you’ve never seen Boston and the harbor from Pier 6’s roof deck, then you’re missing out big time. The chic terrace’s seafood-heavy menu includes a raw bar, steamed mussels, and baked crab cakes, and for your summer sipper, indulge in the house Mai Tai made with Gosling’s and Real McCoy rums. You’re best served by making a reservation ahead of time; visits are maxed out at either 90 minutes or two hours, depending on party size (maxed out at six people).
Daedalus’ sleek upper deck has plenty of tables, shade, twinkly lights, and a fully stocked upstairs bar so you won’t go thirsty. Start your week off or end your weekend right with Sunday brunch (get the stuffed French toast), or show up for an afternoon fueled by mojitos and seasonal beers. To secure your spot, you’re best served by making a reservation on OpenTable.
Legal’s flagship by-the-sea goes overboard with its posh indoor/outdoor rooftop lounge and appropriately named Promenade Deck. And it’s under full sail all four seasons thanks to a retractable glass roof and movable walls. Catch the sunset while slurping infinity oysters, and treat your quaranteam friends to pitchers of punch. Yes, pitchers. There’s also a full sushi menu of refreshing bites, perfect for summertime feasting. Reservations are strongly encouraged.
Felipe’s christened its roof a few years ago, and it’s been a non-stop fiesta ever since (weather permitting). With a ton of tables and umbrellas, it’s the perfect place to knock back a margarita or cerveza, chow down on baja tacos, and mock people in the square who wish they were you. You just might have to wait a bit for that privilege, as the restaurant doesn’t take reservations.
Keeping watch over Cleveland Circle, Cityside’s cozy roof deck is an urban oasis stocked with shady umbrellas and summery beverages. In addition to a lengthy beer list and six kinds of mules, this spot pours an array of thirst-quenching cocktails, like the John Daly (sweet tea vodka, lemonade, iced tea) and a classic mojito. You can make a reservation ahead of time on the restaurant’s website.
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