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What to do in Boston’s Little Italy

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It sounds like something a drunk Red Sox fan would scream outside Yankee Stadium to incite a riot. “The best Little Italy is in Boston” isn’t just an inflammatory remark meant to piss off New Yorkers — it’s a sentiment familiar to many who have visited the small neighborhood in Boston’s North End and enjoyed its unique character, cuisine, and aesthetic.

Chances are, when you think of Boston, you’re thinking of Little Italy. Cobbled streets, waterfront promenades, and historic churches define the North End, which was the first neighborhood in the city. Formerly a bastion of Revolutionary War soldiers, then an Irish district, and a center of Italian culture and cuisine since the early 1900s, the North End isn’t just about spaghetti and meatballs but delicious pastry shops, dozens of festivals, and some of the city’s best nightlife. Sorry, New York. Boston’s Little Italy is the best in the country, and here’s why.

Food like your grandma used to make

Photo: cdrin/Shutterstock

There’s a time and place for cheeseburgers and quesadillas, and the North End isn’t it. When it comes to dining in Little Italy, it’s all about pappardelle, meatballs, fish, and, of course, pizza. If you’re looking for a blend of atmosphere and flavor, it’s tough to go wrong here. To dive right into the Boston Italian culinary experience — and for a pretty good date spot, too — check out Mamma Maria in North Square. Housed in a 19th-century rowhouse, this restaurant has five private dining rooms, a pasta-heavy menu, and panoramic views of the North End.

To take in New England’s fresh seafood tradition with Italian cuisine, head to Rabias Seafood on Salem Street. Try the fra diavolo alla Mediterranea (octopus, shrimp, calamari, clams, mussels, linguine, and tomato sauce) or the gamberi dorati (shrimp, lobster ravioli, roasted red peppers, artichoke hearts, scampi sauce).

Photo: Ernestos Pizza North End/Facebook

No matter how full you may be from dinner, there’s always room for pizza. Take a walk through North Square, check out the waterfront, and before you know it you’ll be ready for second dinner. There’s a hot debate over Boston’s best pizza, with Regina’s (North End) and Santarpio’s (East Boston) regularly winning out, but if you only have one slice in Boston’s Little Italy, make it from Ernesto’s on Salem Street. This little eatery has been a neighborhood favorite for over 30 years and somehow manages to avoid the hype that plagues its competitors.

Leave the gun, take the cannoli

Photo: Joseph Sohm/Shutterstock

Unlike some of its pizza joints, the North End’s more notable dessert spots definitely live up to the hype. Mike’s Pastry on Hanover Street is the most famous pastry shop in Boston, with people regularly coming from outside the city just for a box of their cannolis. Indeed, the “Home of the Cannoli” moniker is well-earned. Since 1946, Mike’s has been a staple of the community, offering up dozens of varieties of cannolis, cookies, pies, and cakes. Just be prepared for a solid 15 minutes of indecision while you figure out which cannoli you want. The options are seemingly endless and include espresso, chocolate mousse, oreo, hazelnut, peanut butter, limoncello, and pecan caramel cannolis.

Photo: Bova’s Bakery/Facebook

Bova’s Bakery on Salem Street is another Boston classic, and it dates even farther back than Mike’s. Since 1926, Bova’s has served the local community homemade Italian cookies, pastries, pies, baked bread, and even sicilian pizza. Between these two pastry shops, you should be able to find any Italian dessert your sweet-tooth desires.

Eat like the Italians, but party like the Irish

Photo: m_sovinskii/Shutterstock

The best part about the North End is that you can pretty much spend the entire day in this part of the city and have a complete Boston experience without needing to venture anywhere else. It’s a given that Little Italy will have an abundance of delicious food, but when Happy Hour rolls around and you start getting thirsty, look no further than North End nightlife.

If you’re someone whose friends are always telling you, “You’re really funny; you should take improv,” then you’re in luck. Assuming they’re not just being sarcastic, the Improv Asylum on Hanover St. is a unique venue that’s probably right up your alley. This improvisational comedy theater puts on several shows every week, which blend sketch comedy and improv scenes. And if you’ve always wanted to try your own hand at improv, they even offer classes in comedy writing, improv, and musical improv.

For those looking for a more fist-bumping nightlife experience, Bell in Hand Tavern is your spot. Claiming to be the oldest bar in Boston — it opened in 1795 — Bell in Hand has something for everyone. The downstairs has live music, a bar, and a dance floor while the upstairs has DJ music, two dancefloors, and two bars. If you tell someone in their 30s you’re going to Bell in Hand, they’ll probably reply with a hint of condescension, “What is it, your 21st birthday?” It’s true, the crowd here is pretty young, but if you’d rather party like a 21-year-old than sip craft beers next to suited young professionals, this is the place for you.

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Written by Anshika

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