Wooster Square Historic District, Historic district in Wooster Square, New Haven, US.

Wooster Square Historic District is a neighborhood in New Haven containing buildings from multiple architectural periods, ranging from Federal style to Victorian brick villas. The streets are defined by closely built residential houses that cluster around a central park.

Development began in the 1820s when sea captains and merchant traders built homes near their commercial operations, converting farmland into residential neighborhoods. This early settlement by prosperous businessmen shaped the area's architectural growth for generations to come.

Wooster Square is known as Little Italy for its Italian American food culture, including the apizza bakeries Frank Pepe Pizzeria Napoletana and Sally's Apizza. A weekly farmer's market, City Seed, runs in the neighborhood, and the Historic Wooster Square Association organizes the annual Cherry Blossom Festival, which drew over 10,000 visitors in 2016.

The neighborhood sits east of downtown New Haven and is bordered by State Street and railroad tracks, making it straightforward to explore on foot. Visitors should expect uneven sidewalks and older streets that reflect the area's age and character.

In the mid-1950s plans called for routing Interstate 91 through Wooster Square Park itself. The Wooster Square Project, begun in 1958 with Yale architecture students, drove a neighborhood revival and the highway was rerouted around the district instead. The rehabilitation was achieved when historic preservation grants and loans were not generally available to homeowners.