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For college students, Tom and Marty's (on Thursdays) and Dillingers are usual favorites. A bunch of the local bars have good food/drink specials throughout the week. The Belmar has Taco Tuesdays, Fitzie's has karaoke on Thursdays, and Sundays at Nips have Trivia and 50-cent wings.
Not many bars for college students in the Caldwell area. Montclair has a few good bars, but is a drive from Caldwell.
Pepe's and Grottas are only good if you're blackout drunk.
New York Pizzeria on N. State Street
Old World Deli is really good, it's on Court Street just over the bridge. Only drawback, it's not open on the weekend.
It's called Cafe Oasis, it's a block from the bars (on Washington Street), and in addition to having a ton of great hookah flavors to choose from, also has a mean sangria.