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, instead of contemplating the broken nature of urban life and the crime it breeds, you’d rather sip on a cocktail and get some sun, then you need to do some research, because the typical characteristics of a good brooding roof - cooing pigeons, shattered glass, and clouds of steam - don’t really make for a good eating and drinking roof. Luckily, we’ve done the work for you. These are the 10 best rooftops in Boston.
The outdoor spots
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.
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.
Lookout Rooftop and Bar
The cocktails at theLookout Rooftop in the Seaport are just OK and they don’t serve food. But the view of Fort Point Channel, the harbor, and the downtown skyline is more than worth drinking some OK cocktails. If the city of Boston needed headshots, it would take them here at this loungy spot with couches, fruity drinks, and lots of people wearing club gear and taking selfies.
Catching a game from the rooftop of the Baseball Tavern is the next best thing to actually going to Fenway. Hell, it may actually be better than being at Fenway if you’re bothered by things like spending lots of money or struggling to walk after you’ve been crammed into a 107-year-old seat for three hours. You can’t see the action on the field from this spot, but you can hear all of it while you’ve got the sun on your face, the game on a TV, and a full bar at your disposal in a place that feels more like a neighborhood pub than a sports bar.
If you can’t get into Lookout, head to the 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.
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 lot better than a Chipotle, 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. It gets pretty busy with the Harvard crowd at night, but it’s worth leaving work early to grab a table.
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 Senor Frogs. But with cabanas, a pool, and cream-colored lounge chairs, the roof at the Revere Hotel in the Theater District comes close to feeling like South Beach (sort of). After 5pm, you can get up here for free (before 5 it’s $20 during the week, $30 on the weekend) and the lobster rolls, sushi, and sandwiches will keep you happy as you get another drink.
How did they get that vintage, ’50s style RV onto 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 enough room to play cornhole, picnic tables, and interesting pub food dishes like chorizo-crusted salmon, this is a great place to spend a Saturday afternoon.
There’s nothing extravagant about the rooftop at the Sinclair - no cabanas, $20 cocktails, or pools that people only dip their legs into instead of actually swim in. But sometimes all you want is a place to sip drinks, share a few bites to eat, and catch the sunset. At the Sinclair, which faces west towards the river, that’s exactly what you can do.
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, umbrellas, and sunshine on the roof.