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Italian Neighborhood Guide: Little Italy New Haven, CT

Rich in culture, pastries, and some of the country’s best pizza, Wooster Street in New Haven is a must-visit.

A state of 3.5 million residents situated between New York City and Boston, Connecticut is rich in Italian tradition in many of its cities, but none has a wider national influence than New Haven. In fact, some in “the nutmeg state” say that “Elm City” is home to the best pizza in America. Most of New Haven’s Little Italy encompasses Wooster Square and the area east of downtown. According to Marc D’Angelo, great-grandson of the founder Libby’s Italian Pastry Shop, and current co-owner of the iconic New Haven establishment, the neighborhood has stayed true to its Italian traditions.

America Domani spoke with D’Angelo about his family’s pastry shop and the Little Italy community centered around Wooster Square in New Haven. “It’s a really cool place because even though it’s dominated by Italian Heritage, you’ll get every race and nationality here,” says D’Angelo. “It’s a very welcoming community.”

HISTORY

Wooster Square, named after David Wooster, a hero of the American Revolutionary War, has been home to many Italian immigrants since the early 1900s. Wooster, a Stratford, CT native, died during the Battle of Ridgefield. Many public places were named to honor his heroic life, most notably, the street that encompasses almost the entirety of New Haven’s Little Italy. 

A plaque telling the History of David Wooster is located in the Middle of Wooster Square Park (Photo Credit: AJ Forrisi)

By the early 1900s, Wooster Street saw an influx of immigrants from Southern Italy in search of the “American Dream.” For Italian immigrants, Wooster Square was essentially a village where everything one needed was within walking distance. 

FOOD AND DRINK

If you’re a fan of thin-crust pizza, you’ll feel at home in Wooster Square. “Pick any of the pizza places, you can’t go wrong,” D’Angelo says with confidence. 

Residents of the New Haven area refer to it as “apizza,” pronounced “ah-beetz.”  The nickname was forged in the late 1800s and early 1900s. The colloquial spelling has long paid tribute to those early Italian settlers in Elm City.

You’ll want to stop at Sally's Apizza on your pizza tour. Established in 1938, their tomato pie is a consistent crowd-pleaser, unlike the notoriously long lines to get into the no-frills pizza shop. This corner restaurant has a strict menu of only pizza, and pizza only, but the limited offerings are worth the wait. 

Located on the corner of Wooster Street and Olive Street, this Apizza place has been serving fine Apizza since 1938 (Photo Credit: AJ Forrisi)

Established in 1925, it’s safe to say that Frank Pepe’s Pizzeria Napoletana is the original pizzeria in Wooster Square. The 2,000-degree coal ovens have been serving Little Italy for a century now, and if you’re a seafood lover you’re going to dig the world-famous clam pizza they have served since the 1930s. A white base consisting of layers of grated cheese, fresh garlic, oregano, olive oil, and New England clams is what makes up this epic pizza. 

The original Frank Pepe's located in between the larger Frank Pepe's and Consiglio's (Photo Credit: AJ Forrisi)

The modern and current Frank Pepe's Restaurant is located in the heart of Wooster Street (Photo Credit: AJ Forrisi)

Modern Apizza is also part of the New Haven pizza “big three.” Located on State Street, Modern is known for its welcoming staff and its famous “Italian Bomb” pie. It’s loaded with bacon, sausage, pepperoni, onions, peppers, and garlic. 

If you’re looking to try any (or all) of these big three pizza places, make sure to give yourself plenty of time as the lines can sometimes be out to the parking lot. If you’re not keen on waiting in line, visit Pepe’s and Sally’s at their other locations around Connecticut and beyond. 

Consiglio’s has been family-operated since 1938 and is considered by many to be the best Italian restaurant in New Haven that isn’t a pizzeria. Eaters rave over the house-made cavatelli and braciola, penne vodka, spicy chicken gorgonzola, and pappardelle.

One of the oldest Italian restaurants in New Haven, opened in 1938 (Photo Credit: AJ Forrisi)

Save room for a pastry from Libby’s, which Liberato and Giuseppina Dell’Amura opened their bakery in 1922. A short walk down the block from Pepe’s on Wooster Street, the family-owned bakery is stocked with traditional Italian cookies, such as biscotti, cannoli, gelato, and more. 

“Liberato was my great grandfather, but they called him ‘Libby’ and that’s where the bakery’s name came from,” D’Angelo says. “We used to be located right across the street, but now we’re in this location which we’ve renovated a lot. We’re going on a hundred years strong.”

Libby's on Wooster Street offers many freshly made Italian pastry's and cookies (Photo Credit: AJ Forrisi)

Over the years, Libby’s has evolved. D’Angelo’s father added the café to the shop in the 70s where customers could grab an espresso or a cappuccino and their signature Italian dessert. 

“I couldn’t give you (a single) most popular menu item because we’ve added so much over the years,” D’Angelo says. “We used to be just cookies, but we’ve added a café and some great pastry as well. The pignoli cookies are a favorite. We also do gelato, and the lemon flavor has been a hit. And of course, our customers love the cannoli.” 

EXPERIENCE

Wooster Square isn’t just pizza and pastries. Yoshino Japanese Cherry Blossom trees were planted in Wooster Square in 1972 and 1973. Wooster Street’s archway is adorned with cherry blossom trees that have evolved into a symbol of the area. The Wooster Square Historic Association holds an annual festival celebrating the cherry blossoms each spring. The trees are in bloom from late March until early May, so a visit during this time will offer a glimpse of the cherry blossoms at their most picturesque time. 

Wooster Square Park is an open park in the heart of Little Italy New Haven, it is the perfect place to have a picnic, take a walk, and enjoy the open air. (Photo Credit: AJ Forrisi)

In 1889, Saint Michael’s Church in Wooster Square was established so that the newly settled Italian immigrants could practice their faith. Bishop Lawrence McMahon spearheaded the process of establishing the parish and nearby temporary places of worship, which for the Italian immigrants at the time were Saint Patrick Hall, The Union Army, and the Boardman Building. Father Vincent Astorri was designated the first pastor of Saint Michael the Archangel parish. Later, he bought and helped develop other churches in the area as the population of Italians began to increase. 

Established as a church for the newly settled Italian immigrants, it helped start the foundation for many other churches in the area (Photo Credit: AJ Forrisi)

There are plenty of annual festivals and markets that help the area maintain its popular tourism. Every June, to celebrate Saint Anthony of Padua, Wooster Square holds a Saint Anthony’s feast which includes a procession and ends with a mass. 

LEGACY

New Haven’s Little Italy sustains the small village vibe that Italian settlers brought with them in the late 1800s. “There are a lot of family-owned businesses here and it’s got that old-school Italian neighborhood feel that’s also very welcoming to tourists,” D’Angelo notes.

New Haven’s Italian community is kept active by the Historic Wooster Square Association, the Wooster Square Cherry Blossom Committee, and the Wooster Square Monument Committee. For foodies traveling through New England, New Haven is a necessary lunch stop. The neighborhood is in good hands with world-class pizza, delicious pastries, weekly markets, and historic catholic churches that have served the community for over a century.  

Marc Stacey

Marc Stacey spent most of his life growing up with his grandparents who immigrated from Calabria. Originally from Bayonne, NJ, Stacey currently works as an Admission Counselor at his alma mater, Fairfield University, where he studied Digital Journalism. He has previous experience as an intern for Outside magazine and as a freelance reporter for the Jersey Journal. 

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