Probably a stupid question but how cold does it get in NYC area in December? I've never been to the North East in the winter, besides Boston last year at the end of February (was like 32 degrees, I remember being miserable waiting in line for a concert lol).

There's a play going on and I can only make it in December, or wait until March, as I assume January/February are the coldest months?

Would be in and out really. Land, go see the play, way by stage door, sleep, fly back.

We were there last December, and the weather went from "comfortable" - which was probably highs in the 40s (warm enough for teenage boys to take their coats off and complain about being hot) to absolutely frigid cold (single digits, maybe even negative at night) when a front came through.

We were in the city as the front came, and it brought rain and wind with it, which made it feel colder. We were wrapping up our visit anyway and heading back to family, and we stayed inside for the next few days, while it was really cold.

Pack accessories like warm socks, hats, gloves, and scarves to keep the extremities warm. Dress in layers. I really hate the cold, so my BF bought me a heated vest. It worked great until it didn't, but I didn't need it except for that one day (and it wasn't working).

My wife and I go the first week of December every year, have been doing this for about a dozen years now.

I've been snowed on, had it get in the 20's, windy and rainy.

I've also gotten a lot of days in the 40s that were absolutely beautiful.

One year it got so warm I was wishing I had brought some shorts.

Bottom line, I've never had weather so terrible that I thought about not going again or changing dates in the future. Look at the forecast and pack accordingly.