The Christmas light House in the Bronx is a neighborhood fixture that is hard to miss. It is decorated year round with life size statues and is painted bright pink. Though it draws most of its audience during the holidays it is an anomaly throughout the seasons. Such a bizarre place with such exuberant colors and vibrancy attracts an artists eye and will draw you in.
This is one of my favorite bars in Manhattan. It has a courtyard in the middle and they only serve a large selection of Belgian beer. It's always dark with red lights so it's like a giant darkroom with everyone developing hangovers instead of film. The courtyard creates a front bar that is open on the weekends, so if you get cornered talking about architecture you can escape over to the front bar and watch people walk down 4th street.
I'm a huge Japanophile: if there's one other place I'd like to live, it's Tokyo. I must have been there seven or eight times, most recently just after the Tohoku earthquake and tsunami. Anyway, EN is a gem on Hudson Street, serving real Japanese cuisine. It turns out that EN is a chain in Japan; there are a lot of branches making lovely bosky food in cosy neighbourhood locations. But their New York incarnation is grand in scale and ambition, with solid, warm interiors (not unlike if the Whitney were a Japanese restaurant, oddly) - a remarkable hybrid of this city, and the other one that I'd love to live in.
The best underground shows you will find will have free pbr and models as far as the eye can see. They are rarely announced, so keep your eyes out for promising openings, especially with Milk Underground coming up.