One of the most fun things to do on a rooftop is to broodingly stare out at the city like you’re Batman. But if you’d rather sip on a cocktail and get some sun, instead of contemplating the broken nature of urban life and the crime it breeds, then you need to do some research, because there just aren’t that many rooftops in Boston where you can eat or drink. Luckily, we’ve done the work for you. Here are all the rooftop patios open right now.
When it built its new complex in Fort Point, Trillium already had a reputation for making the best beer in the city (granted, that’s a statement that would start a lot of arguments). Now it also has a spacious rooftop bar and great food. Order the roasted oysters and one of their approximately 804 New England IPAs, sit in the sun, and know that there are few people in the world enjoying a better beer-drinking experience than you at that precise moment in time.
Does the second floor count as a “rooftop”? Batman would probably find it hard to see the bat signal from there, and all of his fights would draw a crowd of passer-bys, but since those sound like great plot twists for a satirical film, we’ll let it slide. Plus, you can almost see the Chestnut Hill reservoir from the deck at Cityside Tavern, so really, you could also say you spent your weekend sipping Mai Tais “by the water.”
Technically, House of Blues is not open, but the same kitchen crew just opened The Deck on Landsdowne, a rooftop bar on top of the adjacent parking lot. Here you’ll get to sit right under the Green Monster and listen to the sound of baseball, even if you can’t watch it in person (there are also no TV screens here). Eating po-boys on top of a parking garage while listening to baseball - welcome to 2020.
Lookout Rooftop and Bar
The cocktails and food at the Lookout Rooftop in the Seaport are just OK. But the view of Fort Point Channel, the harbor, and the downtown skyline is more than worth eating some just OK food. If the city of Boston needed headshots, it would take them here at this loungy spot with couches, fruity drinks, and lots of people taking selfies.
You may be tempted to swan dive into the harbor from the roof of Legal’s in the Seaport. That’s illegal, dangerous, and gross, so you shouldn’t do it, but nevertheless, that’s how close you are to the water here. The menu features a couple of Legal’s standards like the chowder and lobster roll, but is mostly focused on some decent sushi rolls to go along with raw bar items.
If you can’t get into Lookout, head to the Deck12 at Yotel a block away. You won’t be directly on the channel like you are at Lookout, but you get the same skyline views, the same loungy couch atmosphere, and unlike Lookout, you can even come here for brunch on the weekend.
When you make a reservation at Earl’s, you can request a seat on the patio, but there’s no guarantee of sunshine on your face during the meal. It’s a bit like requesting an empty seat next to you while flying during a pandemic - some companies just shrug and say, “Better luck next time!” At least there are comfortable seats and lobster tostadas at Earls, which we usually prefer to Biscoff cookies.
How did they get that vintage airstream on top of the roof at Coppersmith in Southie? We have no idea, go ask the engineers/wizards who made it happen. All we know is that with picnic tables, a decent draft list, and interesting pub food like crab cake sliders, this is a great place to spend a Saturday afternoon.
Much like a grammarian who looks for mistakes on Twitter, you’ll be equally spoilt for choice at Dorchester Brewing. Their rooftop has high-tops on the deck, picnic tables under a tent, and even more picnic tables in a glass-covered greenhouse, all of which overlook the Boston skyline. There are also 20 beers on tap and M&M BBQ on-site, which means paying attention in English class wasn’t that important after all.
From the street level, Felipe’s in Harvard Square just looks like a standard fast-casual taco place. But if you’ve eaten there, you know that it’s a much better option, and if you’ve gone up to the roof, you know that it’s a great place to spend a couple of hours drinking some strong margaritas and eating big burritos.
There aren’t a lot of things in Boston that could be described as Miami-esque, which we’re mostly fine with. Drinks on the beach would be nice, but we’re good without a bunch of middle-aged men in Guy Fieri shirts trying to find the foam party at Señor Frogs. But with cabanas, a (kiddie) pool, and cream-colored lounge chairs, the roof at the Revere Hotel in the Theater District comes close to approximating South Beach (sort of). The lobster rolls, sandwiches, and churros will keep you happy as you get another drink.
If a great view, space to spread out, and a lot of flowers are not items you require in a rooftop patio, then Cunard Tavern should suit you just fine. While the minimalist patio might not garner the most enthusiastic endorsement from us, at least there are spicy frozen palomas here, which are really all you need on a Friday evening anyway.
For most of the year, Daedalus in Harvard Square is the type of quiet pub where you might see someone reading Shakespeare while eating a burger at the bar. During the summer, it’s the type of place where you might see someone reading Shakespeare while eating a burger surrounded by flower boxes, shade umbrellas, and sunshine. Man, summer’s the freaking best.
So, you really want to go to the North End for a meal. We swear we’ve heard that one before, somewhere. If you’re looking for a rooftop patio as well, then Ristorante Fiore is your only choice. Let’s start with the good news - this patio can be fully covered, if your lunch or dinner happens to be interrupted by an afternoon thunderstorm. The bad news? It’s a fully enclosed space surrounded by brick walls, so you won’t have anything to look out at. But hey, look, there’s some bombolotti on the table!
The view at Pier 6, just like the food, is above average - certainly nothing you’d complain about if you have, hypothetically, spent the last six months quarantined in a tiny apartment. But really the best part about Pier 6 is the free boat ride that you can take over to ReelHouse, which does have the best view of the city. So grab a drink at Pier 6, then scuttle over to ReelHouse for a snack. Rinse and repeat until the sun sets, or at least until the captain catches on.
The beauty of marketing is that you can pretty much say whatever you want. The Colonnade, for example, claims to have Boston’s only rooftop pool. What they mean is that it’s the only rooftop pool for those who don’t have friends residing in the 72 new condo buildings around town with rooftop pools. So you can either make new friends or reserve a spot at The Colonnade for $45 (with an additional $20 minimum food and drink order). The choice is probably dependent on how much your social skills have declined during quarantine.