Why not 

Best contemporary art museum in NY, have to take a train that goes along the Hudson river (best views during fall season!) / rent a car. This museum only uses natural light, and has pieces from Richard Serra, Judd, Sol Lewitt, Walter de Maria, Robert Smithson, Flavin, all best of the best!

This is my go-to spot in my neighborhood. The food is fantastic. They have an ever changing selection of beers and the staff is friendly, attentive and down to earth. Love this place.

Within an couple hours' drive of NYC, you can find lots of sleepy seaside towns. Not only can you get your soft ice cream and salt water taffy on, but you can still spot cool, hand-lettered signs and other relics of a past generation's amusements.

One of my all time favorite shops. They have amazing succulents at reasonable prices. It's always a pleasure to stop in and see what they've got that day. Ched, the owner, is not only extremely knowledgeable but totally hilarious. Every plant has been personalized and anthropomorphized.