Winter planning depends on the weather.
Hi, and Welcome to the Great American Roadtrip Forum.
Your trip at that time of the year will be dependent almost completely on the weather. Whichever route you decide to take, after checking good maps and attractions, you will need to keep an eye on the weather, and then keep your route flexible. If you want to be back in NYC for New Year, keep a day or two up your sleeve, lest you get caught in a storm, and need to take time to sit it out in a nearby hotel.
Also be aware that Niagara Falls, although not frozen over by then, will be in winter mode. None of the services will be open and tours will not be operating. Only the visitor centre on Goat Island will be open. You can't drive up to it, but it is a short walk from the car park. If you want to see the Canadian side of the falls as well (said by most to be the better side), be sure that you can take the rental car into Canada... and that you have the appropriate visas - if applicable.
Lifey