Everyone who is familiar with Hoboken knows about Leo’s Grandevous on 200 Grand Street. Founded in 1939 by an old pal of Frank Sinatra, Leo DiTerrlizzi, Leo’s is still family-owned and is still very much a restaurant of the past (in a good way). Anyone who grew up in this area going to the old-school restaurants in Jersey City, Bayonne, and Hoboken will find the layout and decor of Leo’s pretty familiar (even after a relatively recent remodel at Leo’s). The food, of course, is still famous—classic red sauce Italian fare directly from Tessie DiTerrlizzi’s recipe book. There’s nothing revelatory on the menu, but it’s solid, well-made, and delicious stuff and something of a tradition in the Mile Square (and rightly so). Any night of the week that you’re itching for some great Italian food, Leo’s is a fine choice. Slightly less obvious is the fact that Leo’s is a great bar for meeting up for some cocktails, snacks, and conversation.

Old School Cool

The bar hasn’t changed much in nearly eight decades. It’s still the same semi-circle, with some additional seating space. It’s actually kind of refreshing how simple it is: You walk in, there’s this big spacious bar, lots of light and elbow room. It’s one of those spots where people still sit down in order to chat with whoever happens to walk in, not scream over pounding club beats and order sixteen variations on vodka cranberry. In fact, Leo’s claims to be the oldest restaurant in Hoboken, and we can’t argue, and their web site reports that Men’s Journal once named Leo’s one of the 50 greatest bars in the United States, though we can’t find a link to support that. No reason to doubt it, though; while Leo’s wine list and liquor stocks aren’t filled with unusual choices, it’s one of the most comfortable and reliable spots for a drink in town. The bartenders are friendly without being intrusive, and are happy to offer advice on wines and cocktails. What’s truly remarkable about sitting at the bar at Leo’s is the sense of connection to an earlier age; the photos of Leo and his family, of Sinatra, of other Hoboken notables throughout the years all serve to remind you that this is a place that generations of Hoboken residents have discovered, loved, and enjoyed—a place where the seat you’re occupying as you sip your beer or glass of wine was occupied decades ago by someone else making their way through Hoboken Life. Bottom line: Next time you’ve got a date night, a meeting over drinks, or just some time to kill, stop by Leo’s whether you’re hungry or not. An hour spent sitting at the half-moon bar listening to Sinatra tunes and sipping a drink won’t be wasted.

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