I went for Christmas and New Year of 1995 into 1996
That was just when "The Blizzard of 96" hit North America so snow was insane, cars were trapped, sidewalks could not be used so you had to walk down the middle of the street, all flights were cancelled for 2 weeks so we got stuck there and had to eke out our meagre cash!
Yes, it was cold cold cold cold cold cold cold
The first thing you will do on your first day is go to a department store and buy a bigger coat and boots and hat and gloves and scarf and thermals and cry a little bit
Then you will go enjoy yourself
To be honest I was a bit of a wuss because it gets dark early (like the UK) so mid afternoon it started to get pretty dark on the main streets and totally dark on the side streets, just felt really unsafe to me going down a side street, you couldn't see the shadows and there were lots of potentially crazy people about.
So on the main street it would be all neon and people and then 30 yards away it was a dark alley with tinkling glass and all those old film scenes play through your mind.
Nothing really happened, we were fine, I just felt like a right country bumpkin transported to the big city with bad a$$ city boys hustling and trying to sell tickets and drugs and stuff... bit of an eye-opener for a young country lad.
E.g. going to Central Park was nice, then it gets dark and you have to walk out of the underpass to get out but there are a few people down there and you're thinking "just keep walking, please don't stab me!" but they were probably totally normal people
This is just like all big cities though, depends what you are used to. I'm used to a nice village, not The Village.
The other thing I remember being surprised about was the ****roaches and mice in the apartment - we stayed with a friend of a friend of a friend of a friend and there were probably 10 roaches walking round the room at any one time, and mice running for cover when you opened the door.
I enjoyed it though, don't want to make it sound bad, just pointing out some things to consider.