An easy 2.5 hours drive from the city, Hunter is a great ski destination for the entire family. You have the option to make it a day trip or stay overnight at the wonderful Kaatskill Mountain Club. I would give it an A+ for skiing, an B for overnight stay, B+ for rental gear and a C for food.
I would suggest you pre-rent ski’s, pre purchase your ski pass prior to arrival at Hunter. It is fast to get your rentals if you contracts are printed and ready. If traveling with a tot I suggest you start skiing early in the morning and then take a breakfast break at 10:00AM at the Main Lodge. I would even recommend bringing your entire days food rather than eating here. While there are plenty of food options they are somewhat unhealthy and food courts get very busy at lunch time. Get back on the slopes and enjoy till 2:00PM. Grab a quick snack and hit the mountains till 4.00PM. If you can stay till 6:00pm, you can enjoy snow tubing outside the Kaatskill Mountain Club. They have long runs, fast runs, fun runs and runs for toddlers. After all the fun drive out to the town center – enjoy a somewhat healthy dinner and head back to NYC.