Find It Just east of downtown, Wooster Square is easily accessible by foot, car, or public transit. Follow Chapel Street from downtown into the heart of New Haven’s Little Italy.

Dog It Downtown New Haven is going to the dogs. Convenient to Wooster Square and downtown, Union Square is a selling point for people with dogs looking to move to New Haven. Easy parking, great open space, and lots of friends for your best friend! Union Street between Chapel and Fair Streets.

Wrap It A rich European and Italian heritage and influence, narrow quiet streets, and historic buildings contribute to Wooster Square’s distinctive traits. The neighborhood has a character that is uniquely its own, but is unmistakably New Haven.

NEW HAVEN || EXCEEDING EXPECTATIONS

Wooster Square is a wonderful atmosphere for artists, students, and young professionals.

Visit It

If aromas defined a neighborhood, Wooster Square would be an Italian grandmother’s kitchen. When the local pizza shops light up their coal and wood-fired brick ovens each day, a smoky appetizer drifts through the neighborhood. Towards evening, the smell blends with the garlic and spices from other Italian restaurants and private kitchens. When the breeze is just right, the scent of salty seawater blows in from Long Island to create a bouquet that is distinctly Wooster Square.

Close enough to walk to downtown; Wooster Square is a quiet neighborhood attracting younger residents seeking privacy and convenience. From recent graduates to established professionals, a wide variety of newcomers is introducing a fresh energy to the once predominantly Italian-American Wooster Square area.

The Wooster Square Historic District is an attractive place to visit or call home, thanks to its unique style and character. A number of architectural features grace the narrow streets around Wooster Park. Some of the most stunning homes are an easy walk around the neighborhood:

  • Built in the 1870s, Brownstone Row is an imposing, yet elegant block of Italianate construction that looks like it a crane lifted it right out of New York’s Upper East Side and dropped in New Haven. 552-562 Chapel Street.
  • Also on Chapel Street, the Italian Villa style Oliver North House (c. 1865) wraps around a three-story tower that calls to mind a traditional Italian piazza or castello. 604 Chapel Street.
  • The Reverend Stephen Jewett House (c. 1833) with its austere brick façade and precise structural presentation is one of the oldest homes in Wooster Square and a lasting example of the Second Empire style. 9 Wooster Place.

Throughout the neighborhood, visitors will discover many architectural styles, including Queen Anne, Greek Revival, Federal, and Islamic Revival mixed among more modern New England homes. Each adds its individual flair to Wooster Square’s eclectic mix of structures.

Live It

Wooster Square is a wonderful atmosphere for artists, students, and young professionals. It’s a quiet city neighborhood that would be good for families, too, but kids might find themselves with Wooster Park entirely to themselves on some sunny days.

A compact area with stately stone row homes, multistory conversions, and modern construction, Wooster Square has the character of a New York City block ten times its size and price. It also has a safe homey feel that’s difficult to find in other larger city neighborhoods. The feel and value make it a great alternative for anyone searching for a new home in New Haven.

Wooster Square has a high renter population and its value makes it a delightful stepping-stone to East Rock or Westville. For those starting out in the neighborhood, rents along Chapel Street will approach $1,650 per month for charming apartments with rich wood accents and large windows. For the price, Yale and downtown are a convenient few minute walk or ride. Parking in Wooster Square is a premium, so it is a good neighborhood for walkers and cyclists.

For those who want to call Wooster Square home, buying is a better value than renting. The neighborhood’s real estate cannot be matched when contrasted with similar homes in either New York City or its Connecticut suburbs. Elegant homes in the mid-$300s come with charm, style, and a little bit of New Haven history.

Walk It

New Haven Green A vigorous fifteen-minute walk from most places in Wooster Square, the Green is a gathering place for everyone from students to tourists. Home to summer concerts, impromptu speakers, festivals, and markets, New Haven Green is a favorite destination for locals. Church Street between Chapel and Elm Streets

Knights of Columbus Museum Admission is free to the K. of C. museum and it is an easy walk from Wooster Square. The museum focuses on the history and contributions of the largest lay Catholic organization in the world. 1 State Street (203) 865-0400 kofcmuseum.org

Drive It

Farmington Canal Greenway & Heritage Trail With plenty of free parking, enter the trail at a variety of points along its 84 miles between New Haven and the Massachusetts border. Bring a bike, walk, rollerblade, or cross-country ski through some of Connecticut’s most scenic pedestrian greenways. farmingtoncanal.org

Eat It

Consiglio’s Four generations of the Consiglio family have been bringing traditional delicious and affordable Italian meals to the table since 1938. Make a reservation and go with a group for Sunday Cucina, a family-style four-course meal for everyone because sharing is good! 165 Wooster Street (203) 865-4489 consigliosrestaurant.com

Frank Pepe Pizzeria and Sally’s Apizza While Pepe’s has become an internationally famous destination, Sally’s remains a neighborhood staple with a loyal local fan base. Pepe’s has been making tomato pies since 1925 and Sally’s began making their version in 1938. Try both — eat at Pepe’s original restaurant rather than a franchise knockoff — and decide for yourself. Order a tomato pie with mozzarella and host a Yale-style debate for the best pizza.

  • What’s the difference between APIZZA and PIZZA? New Haven apizza is a traditional thin-crust Neapolitan pie. Say apizza like a local or pizza at either Sally’s or Pepe’s and you’ll get the same thing: crispy chewy charred crust with a thin smear of tomato and a salty sprinkle of pecorino romano.

Pepe’s Arrive early (before 3pm) to beat the lines for a table. 157 Wooster Square (203) 865-5762 pepespizzeria.com

Sally’s Remember, Sally’s only accepts cash, so leave the phones and plastic behind. 237 Wooster Square (203) 624-5271 sallysapizza.com

Abate Restaurant The only complaint about Abate’s pizzas is that they are usually too large! Go hungry and order the Abate Special…it’s not just a big pizza, it’s a big meal on a crust with meatballs, pepperoni, sausage, bacon, and vegetables. 129 Wooster Street (203) 776-4334 abate-restaurant.com.

Tre Scalini Enjoy a touch of elegance and the traditional trattoria style of Wooster Square’s more upscale TreScalini. Start with a melanaze rollatini and then spice it up with pollo scarpiello (chicken with hot cherry peppers). 100 Wooster Square (203) 777-3373 trescalinirestaurant.com

* MUST DO IT!* Modern Apizza Slightly off Wooster Square’s more beaten tourist paths, locals swear by Modern Apizza’s 80-year-old take on the traditional brick-oven thin-crust pie. Purists may disagree, but Modern is the upper-crust of New Haven apizza society. 874 State Street (203) 776-5306 modernapizza.com

Libby’s Italian Pastry Shop Almost on Pepe’s doorstep, Libby’s is the perfect place to take the kids after midday slices and sodas. Treat them to a cookie or Italian ice and then let them run it off in Wooster Square Park. 139 Wooster Square (203) 772-0380 libbyscookies.com

Lucibello’s Italian Pastries Since 1929, Lucibello’s collection of classic old-world pastries remains unrivaled in New Haven. Sicilian and Napoleon cannoli, eclairs, pasticiotti, zeppole, and cream puffs are sure to bring out the sweet tooth and child in anyone. 935 Grand Avenue (203) 562-4083 lucibellospastry.com

Shop It

The Wooster Square Farmer’s Market Over 30 vendors attract neighborhood buyers with locally grown fruits and vegetables, home baked goods, and regional crafts. Look for the Savor tent where they give away incredibly tasty and unusual shortbread cookie samples. Spend a Saturday morning mingling with Wooster Square locals in Russo Park and get to know the neighborhood from the people who live and breathe the area’s history. Russo Park at Chapel Street & DePalma Court cityseed.org

American Memories Browse an extensive collection of collectibles, antiques, and memorabilia. Wooster Square & Chestnut Street (203) 781-6051 americanmemories.com

Atticus Bookstore Café For over 40 years, this independent bookseller has been a staple gathering spot for Yale students and New Haven readers, thinkers, and snackers. While your brain digests the latest publications, let your taste buds enjoy the fresh baked desserts. Your whole body will be happy! 1082 Chapel Street (203) 776-4040 atticusbookstorecafe.com

Chapel Street at the Green Browse the fashion boutiques, jewelry stores, galleries, and curio shops along downtown New Haven’s Chapel Street. A short drive or moderate walk from Wooster Square, Chapel Street is where New Haven meets Yale, new meets old, and fun meets intellect.

See It

Wooster Square Park A small park in the Historic District with access to some water-side trails. Help protect nearby sensitive ecosystems and keep your best friend on a leash. 6th Street and Hallock Avenue. The namesake of the neighborhood, Wooster Square Park is surrounded by historic homes and splendid tree lined streets. Relax in the park with an Italian ice on a hot day or a rich espresso on a cool afternoon. Visit one of the neighborhood’s unique festivals to experience the best of Wooster Square. historicwoostersquare.org

  • St. Andrew the Apostle Annual Italian Festival Every June for the past 117 years, historic Wooster Square comes alive to celebrate Amalfi heritage and traditions. Enjoy free live entertainment, craft vendors, and Italian food.
  • Wooster Square Cherry Blossom Festival Over 10,000 visitors throng Wooster Square’s narrow streets to appreciate nature’s beauty in April. The festival usually features live music, local vendors, and activities for children.

The Old Campus at Yale Walk through Phelps Gate and enter 300 years of history, ivy-lined courtyards, and tradition. Wander the campus or join a student-led tour to learn notable facts about Yale and earn a degree in local history and lore. 344 College Street (203) 432-4771 yale.edu

Yale University Art Gallery A few minutes’ walk up Chapel Street, the Gallery is free to the public and houses regular and travelling collections from around the world. Visit the sculpture garden in the courtyard or the permanent collection Art of the Ancient Americas. 1111 Chapel Street (203) 432-0600 artgallery.yale.edu