On one auspicious day in April 1939; Leo and Tessie DiTerlizzi opened a tavern on second and Grand Street; “the rest is history”. Leo’s Grandevous, a rendezvous on Grand Street, would become one of Hoboken’s oldest family owned and operated restaurants. Leo & Tessie lived the “American Dream”. Through hard work and perseverance, they managed to build their clientele one customer at a time.

Over the years Tessie began serving dinners prepared from her own kitchen in the apartment above the bar. As additional storefronts became available; Leo and Tessie expanded the Tavern into the restaurant that exists today.

Leo and Tessie also developed an affinity for Hoboken’s favorite son Frank Sinatra. As Sinatra became more famous, he found his place in Leo’s heart as well as the wall’s and jukebox of the restaurant. Sinatra’s music would resonate while dining on Tessie’s homemade favorites. In fact William Bunch author of “Jukebox America” St. Martin’s Press dubbed our jukebox “The Worlds Greatest Frank Sinatra Jukebox”.

“Hoboken’s, little town blues were blown away,” in an article by Sarah Vowel of GQ Magazine, May 1998, in which she celebrated Frank Sinatra’s humble beginning in Hoboken. The town and friends that helped forge his life and career. As well as the friendship Frank Sinatra and Leo maintained as young men.

Over the years Leo’s has survived many generations of families and friends but anyone you speak with has their own favorite “Leo’s” story. We often encounter a member of a third generation whose parents and grand parents had their start in Hoboken and now they have come full circle. Leo’s is one of the only familiar things left in Hoboken that elder generations can associate their younger lives with.

Today Leo’s has maintained itself as a comfortable meeting place where you can find a friendly face, a great meal, and some wonderful music and refreshment. Men’s Journal named Leo’s as one of the “50 Greatest Bars in the United States” in their humble opinion, January 2002.

Well their opinion is unanimous! Leo’s has served Hoboken for 66 years. Our recipe for success has been to serve only the best quality food, with spirits to fill and enhance your mood while listening to timeless music.