Wooster Square - New Haven, CT

 Immediately east of downtown, New Haven’s “Little Italy” is anchored by a vibrant park bordered by the mansions owned by ship captains during the city’s shipping era. The Italian residents who made the neighborhood home in the 20th century rallied to save that and other beautiful architecture, including numerous elegant brownstones, from the wrecking ball.

The community activism and neighborliness they brought to the area survives today. Residents organize an annual festival to celebrate the blossoming of the park’s cherry trees. Artists in the neighborhood use coffee shops like Fuel as a gathering spot. A lively farmer’s market sets up on Saturdays during the growing season. And this may be the most dog-friendly neighborhood in the city, right down to the doggie drinking fountain in the park.

But Wooster Square is best known for its food—specifically for Sally’s and Pepe’s which battle every evening in a decades-long competition for the title of the country’s best pizza. (Legend has it that Frank Pepe introduced the “tomato pie” to America at his original brick oven still operating on Wooster Street.) The city’s best-known Italian restaurants are also here, and no one ever heads home without a stop for pastries at either Libby’s or Lucibello’s.

Nearby schools include Conte Magnet School, High School in the Community and Elm City College Prep-Elementary.