We should all get some kind of financial reward for surviving a bitterly cold Boston winter and a spring that has serious commitment issues. But since we don’t live in a wealthy Gulf oil state where the government can give each citizen an annual stipend, we’ll have to settle for the next best thing: our Outdoor Greatest Hits. These are our all-time favorite places for eating and drinking outside, and they’re where you’ll want to be during those few weeks of the year when the outside world is exceedingly pleasant.
the outdoor spots
The patio at Oleana in the Port is what you imagine your backyard is going to look like when you make that first trip to Home Depot in the Spring. But whereas you will inevitably end up with mismatched plastic chairs, a broken grill, and a weed-strewn vegetable patch, Oleana’s patio is nothing but rock gardens, hanging lanterns, and ornamental trees that look like they house magical forest elves. The fact that it’s hidden from the street to give you a quiet spot to enjoy the great meze menu makes it all the better.
Planting yourself at a bar to watch the game and to use the bartender as a cheaper alternative to therapy is always fun. But planting yourself at a bar to stare out over the rooftops of Fort Point is even better. That’s what you can do at Trillium, which not only has tables on its rooftop, but also a long countertop with barstools on the ledge. You probably already know how great Trilllium’s beer is, but if you haven’t been here yet, know that the American menu is excellent too (start with the baked oysters). And if you’re afraid of heights, they’ve also got a patio on the ground floor courtyard.
Not all of us can be a former US Secretary of State who lives with a ketchup heiress in a Beacon Hill mansion. But at the Hungry I, we can pretend to be one for a night. The hidden patio behind this restaurant housed in a 19th-century townhouse looks like a private sculpture garden, and the fact that there are only a few tables out here keeps it quiet, romantic, and makes it one of the best places in the city to propose to someone (or at least offer to share an Amazon Prime account). Order a bottle of wine, get the duck l’orange or the venison, and feel like the invited guest of an old-world aristocrat.
Reelhouse on the Eastie waterfront is a great place to go if you have pinkeye or a really bad haircut. That’s because the wide views of the harbor and the downtown skyline are so stunning that no one at the table will be looking at each other. You’ll all just be staring out at the ferries, sailboats, and glowing Custom House Tower as you split the shellfish platter or Malaysian style chicken wings (though if you have pinkeye, maybe you should skip the communal eating). The patio out back is huge and has an outdoor bar, making the whole place feel like a party - we suspect that the average time spent here by people who get seats a is just under five hours.
We should all know where our food comes from. Whether you’re on the roof deck or at one of the tables on the Harborwalk at Legal Harborside in the Seaport, you’re close enough to the sea to practically see the fish jumping (and if you can’t see the fish in the water, you can definitely see the catches being unloaded on the fish pier next door). Legal’s became a New England institution because the seafood is reliably great, and this location is by far the most fun of them all.
Lookout Rooftop and Bar
At the Lookout Rooftop Bar, you feel like a drone hovering over Fort Point Channel spying on the harbor and downtown skyline. Simply put, it’s got the best views of any rooftop in the city. The fruity cocktails are just OK and there’s no food, but you won’t mind when you’re lounging on a couch and wondering whether you should kickstart your music career for the sole purpose of one day filming a music video up here.
Thankfully, the side of truth and justice is winning the war against beer gardens, which means that Boston will once again have so many this summer that you can practically go to a different one every single weekend between now and Labor Day. Our favorite, though, is Night Shift’s Esplanade location. Even the most devout atheist would admit that drinking New England IPAs under swaying trees and string lights while sailboats gently tack in the Charles is proof that someone, somewhere wants human beings to be happy.
With white lights strung overhead, classy wooden decking, and stone walls filled with planters, the sunken patio at B&G will be a great place for your second or third wedding, the one that’s just you, your adult kids, the nice stable dentist you met at a yoga retreat, and a lot of rosé. Until that day arrives, though, come to this South End spot to have what amounts to close to a perfect summer evening with great seafood that’s better than your local clam shack (think rock shrimp ceviche with huckleberries and whole branzino with fennel).
The eight blocks of Comm Ave that run from the Public Garden to Mass Ave are the prettiest section of any street in any city in America. And Buttermilk and Bourbon, a Southern place on the corner of Dartmouth and Commonwealth, is the only restaurant on the entire stretch. That would be reason enough to grab a table or a seat on one of the couches on their sunken patio, but it’s also got a great menu that works particularly well for Sunday brunch. Unless you’re the greatest football player of all-time and married to a supermodel, you probably can’t afford to live in one of the mansions here. But sit outside with a sazerac and some oysters and you can pretend you do.
Sullivan’s doesn’t technically have any outdoor space of its own. But it’s a clam shack on Castle Island in Southie, which means that you can order a box of fried clam bellies and a lobster roll and go sit down on the sand and eat it with your toes dipped in the water. Frankly, if you want anything more out of summer than that, then you’re being My Super Sweet 16 level needy.