One of America’s oldest operating pizzerias and fresh off its latest expansion, this Connecticut institution has been welcoming generations of families since 1935.

In 1918, Neapolitan immigrants Alfonso DeSimone Sr. and his wife, Assunta, were earning local approval with their Savoy Bakery business, operated out of the back of their three-family home in Bridgeport, Connecticut. But they grabbed a chance to enter the pizza biz in 1945 when a friend, Jerry Curcurello, who’d opened Jennie’s Pizzeria (named after his wife) 10 years earlier, offered to sell to Alfonso Sr.

His son, Alfonso Jr., and his two sons-in-law assumed ownership of the pizzeria—and today, the third and fourth generations continue the operation: Al and Richard DeSimone (sons of Alfonso Jr.) and their wives, Regina and Eva, own the still-thriving business. Their kids also pitch in to help with modern-day demands, like social media and graphic design. “We’re all bakers, our whole family—we learned from my grandfather,” Al says, calling Jennie’s pizzas a cross between New York and New Haven styles. “The original dough recipe we still use today was the one my grandfather developed back in Italy.”

Al notes that Jennie’s is now the second-oldest pizzeria in Connecticut and the 17th-oldest in the country. Thanks to its enduring success, there have been a few moves to expand operations over the years—three within Bridgeport before taking its current spot in Monroe in 1998. Jennie’s was again renovated and expanded in 2021 and now offers a 6,800-square-foot space with a separate room for private parties, plus full bar and lounge. “My grandfather had a slogan from his bakery: Taste proves quality,” Al says. “That’s what we’ve followed ever since. Give ’em a good product and a reasonable price, and you’ll never go wrong. There must be something to it!”

Alfonso Sr. also taught the next generations to treat people the way they want to be treated—and that extends to relentless community give-back efforts, as well as employees and customers. “We consider a lot of our customers like family, and they consider us family,” Al says. “That’s how far back it goes—we have customers now whose parents and grandparents took them to Jennie’s when they were small. We’ve had dishwashers and waitresses work for us 35, 40 years. You don’t find that in the restaurant business. With us, it’s not about the bottom line at all. When people tell us how much they enjoy our food, ambience and employees, that makes it all worthwhile. It’s really close to home, close to our heart, and we put a lot into it.”  

Tracy Morin is PMQ’s senior copy editor and the editor of PizzaVegan.com.