Where To Eat And Drink In Jamaica PlainOur 15 favorite spots in the neighborhood.
Every Boston neighborhood has its stereotypes, but JP seems to have 18 of them. But somehow, all of them make sense, because this neighborhood really does seem to offer something for everyone. When it comes to eating and drinking, it’s all here - restaurants that use the word “seasonal” with near-religious reverence, cafes where everyone looks like they play bass, Caribbean places with pictures of David Ortiz on the wall, sandwich shops that host fundraisers for LGBTQ advocacy, and low-key bars where construction workers drink next to the doctors. Jamaica Plain is a hard place to define, but a great place to hang out in. Start with these 15 restaurants and bars.
There are a few things we can’t figure out about Yely's Coffee Shop. We can’t figure out how much anything costs, because there isn’t really a menu - you just point to a bunch of stuff under glass, and it almost always comes to about $10. We can’t figure out why they have a poster of sandwiches on the wall despite the fact that they don’t appear to serve sandwiches. And we don’t know why it’s called a coffee shop when we’ve never seen anyone order coffee here. But we do know that the Dominican food is outstanding - we’d pay way more than $10 for the ribs alone, and have enjoyed everything we’ve ever ordered here. If you commute via the Jackson Square T stop and don’t stop at Yely’s on your way home at least once a week, then you could medal in the Self-Restraint Olympics.
There are thousands of Irish pubs in Boston, and the Behan is better than every one of them. It’s comfortable, has an extensive selection of craft beer, and it makes you wish you were an Irish poet writing in a leather-bound notebook that smells of whiskey and rain. There’s no food here (though occasionally someone might pop-in to sell empanadas) but you don’t need it. This is the perfect place to get a few drinks with friends - and it’s one of the only indoor places in Boston where some of those friends can have four legs.
Brassica is the type of small plates place where you’ll wish you could eat through the entire menu. And here, you can actually do that, because $100 gets you all 19 dishes they serve. The menu changes with the seasons (as you’d expect from a place in JP that displays works by local artists on the wall). What makes the place even better is that it serves an excellent brunch on Saturdays and Sundays. This place is awesome.
Turtle Swamp is smaller than a lot of other Boston breweries that could host adult dodgeball leagues, but that just makes the atmosphere in this converted mechanic’s garage that much more chill. It has a great courtyard that’s set back off Washington, a space with a ton of natural light thanks to those old garage doors, and the Orange Line is an excellent New England IPA. For an even cooler experience, head upstairs to the semi-hidden room with bench seating and board games.
Tres Gatos doesn’t have the best food of the restaurants on this list. While there are a few dishes at this tapas place that we love, there are just as many that don’t really hit their mark (the patatas bravas). And yet, it’s the first place we take people to when we want to show them JP, because it’s a tiny little cabin that is equal parts restaurant, bookstore, and record store where everyone’s always having fun. The cocktails are great, and drinking them on the shaded patio overlooking Centre Street is a perfect way to spend a warm night.
Ten Tables is close to the ideal neighborhood restaurant, a place with a seasonal menu where just about everyone who comes in seems to be familiar with the staff. It’s tiny, with only a handful of tables on one side of the dining room, and a small bar on the other. But it doesn’t get claustrophobic and that bar is the kind where you’d consider bringing a book. And the monthly themed wine dinners are a good excuse to keep coming. You won’t really need an excuse, though - it’s the type of place that, if someone suggests going to, you’ll agree without needing to think about it.
You hear Alex’s Chimis before you see it, thanks to the guy behind the counter who spends all day taking a giant cleaver to the perfectly roasted chicken at this counter-service spot in Hyde Square. There’s a decent-sized Dominican menu of things like pork ears and chimichurri burgers here, but it’s that chicken that will keep you coming back (and make you want to get a meat cleaver, because man, that looks fun).
A burger and a beer is one of humanity’s most perfect combinations, right in between day drinking on a day-off, and Pedro and David Ortiz. And that's what you'll want at this tiny corner spot on Centre Street. They've got a selection of other sandwiches, pizzas, and salads on the menu along with wine and cocktails - but the wine list is small, the cocktails are only made with cordials, and the sandwiches aren’t as good as the juicy, nicely cooked burgers that come topped with things like onion rings and homemade BBQ sauce.
Keep The Haven in mind the next time we get a snowstorm during that early part of winter, when the sight of snow makes you want to sit next to a fire and watch the Hallmark Channel, instead of contemplating how to single-handedly punch another hole in the ozone layer so that you never have to shovel your car out again. This little Scottish hunting lodge of a pub in Hyde Square unsurprisingly has one of the best Scotch menus in the city, along with a good menu of things that Scottish lords probably hunt on whatever a moor is, like the white pudding sassitch and mash.
Everything about Vee Vee is tiny. It seats fewer people than you need to get a pick-up soccer game going, the wine list fits on an index card, and if you went two or three times you’d probably feel like you ate your way through the entire menu. The effect is that it feels like a friend’s living room, but the menu changes with the seasons to keep you interested with things like potato-crusted pollock and crispy mushrooms with sriracha soy sauce. There are a lot of JP restaurants that love to use the word “farm” a ton, and while Vee Vee can sometimes get lost in the crowd, we never regret coming here.
The first thing you may notice when you walk into El Oriental de Cuba are the button-down shirts hanging in dry-cleaner plastic towards the back. We have no idea why they’re there, but it’s not important, because the second thing you’ll notice is a menu of big Cuban specialties. The empanadas are among our favorite in the city thanks to perfectly flaky crusts and meaty fillings, and the Cuban sandwich is excellent. They don’t have a liquor license and not everything on the menu is a hit (the mofongo is a little dry), but this is a great option when you want some big plates of pork or chicken.
The fact that Canary Square is one of the only places in Boston where you can reliably find multiple varieties of Trillium on tap (other than the brewery, of course) is reason enough to come here. But if that’s not enough, it’s also the type of all-around solid restaurant that works when you just can’t figure out where to go. Its big space and gastropub-type menu makes it ideal for groups, and the patio overlooking Hyde Square is great when the weather’s nice.
On a per capita basis, JP seems to have more coffee shops filled with people whose jobs somehow allow them to hang out in coffee shops all day than any other Boston neighborhood. Our favorite, though, is Ula Cafe in the brewery complex on Armory. The sandwiches here are legitimately good - not just good in the sense that they get the job done so you don’t feel bad about using their wifi for three hours - and there are a ton of vegan options that anyone would enjoy, like the curried tofu. It also helps that this place is a little less polished than the Neros of the world, making it feel more like a place run by a bunch of friends than a place run by people in boardrooms trying to figure out what the kids are into these days.
Sweet Rice probably makes a killing delivering both Thai and sushi every night, but it’s worth dining in at this colorful spot with a bar and a bunch of countertop tables overlooking Centre Street. We like the Thai food slightly more than the sushi (you’ll be tempted to order the pineapple fried rice every time you come) but both are worth your time and money.
The Midway Cafe is what every new bar hopes it will be like in 30 years - a place with more worn-in character than your grandfather’s favorite hat. Part punk bar, part union hall, part after-work drinking spot for the overworked and underpaid teachers from Boston English across the street, it’s one of the realest places in the city. The drinks aren’t really anything special and there’s no food, but it’s a hell of a lot of fun thanks to live music almost every night, and Queeraoke on Thursday is something everyone who lives in JP should experience at least once.