By Tracy Morin
With more than a century of craftsmanship—centered around Wooster Street—cementing New Haven, Connecticut, as an international pizza hot spot, traditional New Haven-style pizza deserves its legendary status. But another player entered the space in late 2023 and is hoping to make its own mark on the history books with a different spin on local pies, dubbed “Wooster Squares.”
Avi Szapiro and Tim Cabral, the owners and masterminds behind Gioia, not only opened a full-service Italian restaurant, the concept also includes a market, gelateria and rooftop space. Offering pizza on Wooster Street, they knew, would require a delicate balance—so they did something completely different from their neighbors. Rather than trying to compete with the traditional New Haven-style pies made famous by icons like Frank Pepe and Sally’s, they crafted thicker-crust square pies with unique toppings.
These Wooster Squares include creative options such as Goat Cheese (with truffled ricotta, Parmesan, red onion, pistachio and honey), Mashed Potato (ricotta, Taleggio, rosemary and crispy garlic) and Pepperoni (tomato, mozzarella and pickled jalapeño). Meanwhile, the rooftop menu differs from the main restaurant, offering the Goombah (steak, whipped ricotta, American cheese and caramelized onion) and the Mushroom (whipped ricotta, spinach, Parmesan and garlic aioli). Slices are also available via a streetside window, where Gioia’s sells its gelato.
Szapiro, executive chef and co-founder of Gioia, recently told PMQ more about the concept—its inspiration, how it stands out among world-famous local competition, and how guests are responding.
PMQ: How did the Gioia concept begin?
Avi Szapiro: Tim and I met while operating from the same building at The Taft in New Haven. Tim’s bar, Ordinary, was on one side, and my restaurant, Roia, was on the other. We shared similar values about quality of product, hospitality and the passion we have for the industry. That’s what got us wanting to work together.
Then COVID hit. We both had to shut our establishments down, and it provided the opportunity to do something together. That’s how we landed on Wooster Street.
We have both spent our lives in hospitality—restaurants, bars, building teams, opening concepts. Gioia came from a shared desire to create a place that’s fun, with great food and drinks, great energy, and many options—including the market, the gelateria, the rooftop and the main dining room.
PMQ: How did you have the confidence to open a pizzeria on Wooster Street?
Szapiro: Confidence is a strong word. We didn’t come in thinking we were going to compete with institutions; we came in wanting to contribute to the neighborhood. We saw an opportunity beyond just pizza—a market, a serious bar program, gelato, a rooftop—and believed we could build something that adds to Wooster Street in a different way.
PMQ: Is that why you decided not to offer the typical New Haven-style pizza?
Szapiro: How would you even begin to compete with Pepe’s or Sally’s? A) We’re not that smart, and B) we’re not crazy, either!
So the starting point was simple: We had to be different. We explored every style of pizza—Roman, Detroit, Sicilian—and landed on something that felt right for us: an airy, thicker dough with a real crunch on the crust. It took months of testing and help from a great baker friend from New Haven, but we knew we had something once it felt like its own thing—not a copy, and more grandma-style than anything else.
PMQ: Tell us about the menu development and creative topping combinations.
Szapiro: We see pizza as a great vehicle for flavor; it’s super versatile and dynamic, and a good dough is a delicious thing. Some ideas work, some don’t, and we’re OK with that. We’ve messed up plenty of times, but every miss teaches us. The menu pulls from everywhere—Italian tradition, Italian-American nostalgia, the seasons and our team’s creativity. At the end of the day, the guest decides if we got it right.
PMQ: And what has the guest response been like?
Szapiro: We didn’t know how people would respond, but we’ve been pleasantly surprised and utterly grateful. Our pizza has become a great-performing item for us, both in the restaurant and at the gelato window. A lot of people doing the New Haven pizza tour come in skeptical and leave as fans. Being the only spot on Wooster selling slices (at the gelato window) has also helped us contribute to the neighborhood.
Pizza fits naturally into Gioia because it’s approachable—it brings people in. Whether you’re grabbing a quick slice at the window, sitting down for dinner or heading up to the rooftop, pizza connects all parts of the experience. It’s familiar, but it also gives us room to be creative. Plus, who doesn’t love pizza?
PMQ: How does the rooftop menu differ from the main dining room, and why did you decide on that two-menu approach?
Szapiro: The rooftop is more casual, more playful—we take bigger risks up there. Downstairs leans a bit more restrained, while upstairs gives us freedom to experiment. Since the rooftop changes concept a few times a year (such as our winter activation, The Red Sauce Joint), the menu evolves with it. It keeps things fresh for us and for the guests.
PMQ: What is The Red Sauce Joint?
Szapiro: In addition to the summer rooftop experience, we run two (now annual) activations each year. “The Red Sauce Joint by Gioia,” running from January 16 to April 26, 2026, on its fully enclosed and heated rooftop space overlooking Wooster Street, offers an inviting, nostalgic space inspired by classic and beloved Italian-American eateries. The activation blends this timeless culture and treasured environment—including red and white checkered tables, warm string lights, classic Italian greenery, wicker-wrapped Chianti bottles, old-school photos on the walls of regular guests and cured Italian food products—with Gioia’s signature charm, warmth and fun, with a menu featuring classic and familiar Italian-American cuisine and beverages.
The “Joy-ah for the Holidays! A Winter Wonderland” activation runs through the holiday season. The rooftop space, which is heated and enclosed for the cooler weather, is transformed into a winter wonderland through December 28. The space features holiday decorations everywhere the eye can spy, including holiday lights, wreaths, Christmas trees, ornaments, inflatables, garland and more, creating a playful and festive space to celebrate the holiday season. In 2025, the special pop-up food and beverage menu included White Christmas Mojito, Mule Ride, Peppermintini and Santa’s Cookie Old Fashioned cocktails, as well as Chicken & Dumplings, Ossobuco Milanese, and Mac and Cheese, among other items, on the food menu.
PMQ: What are your plans for the future of Gioia?
Szapiro: We focus on the guest today—how do we make their experience better, right now? If that ends up contributing to New Haven’s pizza story, we’re honored. But we’re not trying to define that story—we’re just happy to be part of it, doing what we love.
Tracy Morin is PMQ’s associate editor.
