First, there was the close call with the Andrea Doria. Apparently, Alessandro Milanese’s family was supposed to have left Italy, ultimately bound for Poughkeepsie, on the infamous July 1956 trip when the grand Italian ocean liner hit another boat and sank. It was only his grandfather’s lack of correct documents that kept the family from boarding the ship at the very last minute. The family did arrive in Dutchess County a few weeks later, and 15 years after that, Alessandro’s father, Santino, opened the Milanese Italian Restaurant on Poughkeepsie’s Main Street.
The date was November 13, 1971, and as family legend holds, there was only one customer that night: a truck driver who stopped to ask for directions. It seemed like an ominous sign for a new business, but clearly, the Milanese Italian Restaurant was meant to be. Because while the family watched Poughkeepsie fall into urban blight, then climb back up again; and while other restaurants have come and gone, Milanese — with its telltale neon sign lighting up the western end of Main Street — remains one of the city’s most enduring landmarks 40 years later.
It was a family affair from the get-go. Santino’s wife, Rita, manned the kitchen, while other extended family members acted as waiters. Young Alessandro and his brother, Aldo, lived with their family upstairs and spent their childhoods romping around the city’s Little Italy section, as well as in a fenced-in yard out back. They, too, learned the tricks of the restaurant trade. Not all that much has changed in the past four decades; the building was expanded a bit, the menu tinkered with here and there, and eventually Alessandro and Aldo took over from their parents. “But they are still here almost every night,” says Alessandro. “They sit in the corner of the bar and play cards with their friends; they go around and greet people. My father still comes in and butchers the veal and the chicken himself.”
The food quality hasn’t changed either. “Everything is still homemade,” says Alessandro, noting that classics like veal or chicken parmigiana remain the most popular items on the extensive menu, which includes a traditional selection of pastas, chicken, veal, beef, and fish. Alessandro also credits the bolognese sauce with keeping their customers content. “The secret is to keep it simple and use really good tomatoes; don’t skimp on the tomatoes. But you don’t want to over-spice and use too much oregano or too much black pepper. If you have good tomatoes they’ll do a lot of the work. After that, I don’t think I should share any other secrets.” These days, the next generation buses and waits tables, and an endless stream of chatter — both in Italian and English — fills the eatery’s three rooms. The restaurant’s most popular days remain Easter Sunday and Christmas Eve, but regulars continue to come all year-round, including a group of judges from up the road every Thursday. A $18.95 three-course special on Tuesdays, Wednesdays, and Thursdays also helps to attract diners, and parties — communions, birthdays, retirements — are regularly accommodated here. And while the menus and the restaurant itself — which seats almost 200 people — seem a bit dated, it’s exactly that old-fashioned family feeling that seems to work so well. Says regular Mick Feola, “I come here all the time because the food is good, the prices are right, and it feels like I’m eating at my grandmother’s house.”