Rocco DePasquale left Italy for America in 1914. He made his way to Boston and settled in the North End where he worked as a baker for the people who opened Pizzeria Regina. When he married, he moved to East Boston and opened a bakery which is now called Tony's, and is still open today.

On July 4, 1940, Rocco opened the doors of Rocco's Restaurant with his wife, Angela, and their children, Tony, Jo-Jo, Phil, Rocco, and Rose. They served spaghetti and meatballs for years. They baked their pizzas in a coal-fire hearth until the early 1960's. A cheese pizza cost $1.00.

In 1963, Rocco V. DePasquale took over Rocco's, his brothers all having their own businesses as bakers or running DePasquale Brothers. In addition to their Italian meals, Rocco made downy-flake doughnuts and served ice cream from their soda fountain. He added a glass atrium to the restaurant as well as a Groceria from which he sold cold cuts, take-out items, and rotisserie chicken. He introduced dishes such as Chicken, Broccoli, and Penne and Fettuccine Alfredo to the menu.

Rocco fought for a liquor license in the 1970s. Before 1974, customers had to bring their own beer and wine with them. The actual bar that is in the restaurant today was built in 1996. In 1997, Rocco turned the restaurant over to two of his sons. Rocco Jr., "Chuck," as everyone calls him, and Matt recently updated the restaurant, exposing the original stonework their grandfather built and giving the place a Tuscan feel complete with a mural of a Tuscan countryside and an indoor water fountain. They have added to the menu favorites such as Buffalo Chicken, Rattlesnake Pasta, and Chicken Florentine while keeping all the traditional favorites that have made them famous over the years: Eggplant Parmigiana, Chicken Marsala, and of course, pizza and calzones.