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The Oldest Italian Establishments in Boston

It’s no secret Boston is a hotspot for Italians. It was once home to a major enclave of southern Italian immigrants in the 19th and 20th centuries who fled famine, disease, and high mortality rates in the hopes of cashing in on the sogno Americano, the American dream. Drawn to the city’s close proximity to the ocean and the opportunities that could be found as commercial fishermen, many of these Italians eventually settled into what is today known as the North End, a one-square-mile neighborhood hovering on the edge of the city’s waterfront. Packed with Italian restaurants, delis, coffee and pastry shops, it’s one of the country’s most vibrant and enduring Little Italys. 

Take a look at the city’s four oldest Italian establishments for your next trip to Boston.

Pizzeria Regina (1926)

Located on Thacher Street in Boston’s North End, Pizzeria Regina is Boston’s oldest pizzeria, serving up brick-oven, thin-crust pizza since 1926. Opened by Luigi D’Auria, the iconic, no-frills joint has been run by the Polcari family since 1956 and is famous for its crunchy crust, which derives from a secret, century-old family recipe. While its North End location remains its most popular, the pizzeria has several outposts across Massachusetts and New England.

Caffe Vittoria (1929)

This old-school coffee shop positioned on Hanover Street in the North End has been open since 1929. The cash-only establishment has four floors decorated with simple, metal-rimmed chairs and tables, worn marble floors, and dozens of old-school coffee machines and espresso makers stretching as far back as the early 1900s. Famous for its coffee, pastries, and hot chocolates, Caffe Vittoria also sells ice cream and a wide range of beers, wines, and cocktails.

Santarpio’s Pizza (1930s)

Originally opened as a bakery in 1903 by Frank Santarpio, the East Boston establishment was converted into a pizzeria in the 1930s. Here, the neighborhood institution makes New York-style pies with a twist: the toppings are baked beneath the sauce, which supposedly packs the dough with more flavor. Santarpio’s Pizza has an additional location in Peabody, MA.

Cantina Italiana (1931)

Also located on Hanover Street in the North End, Cantina Italiana ranks as the neighborhood’s oldest restaurant. Open since 1931, it serves hearty portions of old-school classics like spaghetti aglio e olio, parmigiana, and veal chop Milanese. The restaurant also boasts an extensive wine, cocktail, and beer list for a perfect pairing to any dish.

Asia London Palomba

Asia London Palomba is a trilingual freelance journalist from Rome, Italy. In the past, her work on culture, travel, and history has been published in The Boston Globe, Atlas Obscura, The Christian Science Monitor, and Grub Street, New York Magazine's food section. In her free time, Asia enjoys traveling home to Italy to spend time with family and friends, drinking Hugo Spritzes, and making her nonna's homemade cavatelli.