Dia:Beacon is a short train ride from the city in a former Nabisco box printing factory. This art foundation has 240,000 square feet of art from the 1960s to the present. Dia features the work of Sol LeWitt, Imi Knoebel, Andy Warhol, Dan Flavin, Agnes Martin, On Kawara, Bruce Nauman, and many others. I love going during the summer to enjoy the gardens surronding the building.

This burlesque club contains a stripper pole, but is hardly worth it unless you know someone who will hook up drinks.

Webster Hall is a solid venue, and a frequent stop for many great bands on their rise to glory. If you've only got a few nights in the city, chances are a great act will be playing here.

Part of the Marlow restaurant group, Diner is one of the more casual / rustic options. The menu changes daily and is written out (most likely upside down by the wait staff) on your table or the back of a receipt. The only constant item is the burger, which to be honest, is one of the best in the neighborhood. If they have a breakfast sandwich for brunch, get that. The fried chicken sandwich (with dark meat) is also a favorite. They make scrambled egg dishes better than most. Dinner is solid all around (they crush a steak for two). Homemade ketchup and dijon mustard are on every table, so regardless of what you get, these two condiments are worth the visit. 

I buy gigantic dry-aged steaks and 1.5-inch pork chops here. The staff is really friendly and helpful.