Northern New England is already fairly cold, and getting colder every day (and night!). You have about a month til heavy snow starts, which will last no longer than March or April (or late May in a cold year).
You say you have winter gear, but many roads may not be very rideable for months at a time. Even with very fat studded tires, riding a loaded bike in snow/ice is very very difficult, and no fun at all. Without very fat studded tires, it will probably not even be possible. Schwalbe makes good snow tires in most sizes if you decide to give it a go.
Heading south down the coast from WV might be a better option at this time of year. As Jonathan Richman said, "I love New England", but spring aka mud season, or better yet summer (basically July and August (in a good year)), or early fall are much better times of year than now.
Also, coastal areas are much flatter. Upstate NY -> Maine involves traversing some pretty big mountains- nothing compared to the Rockies of course, but you may get a bit winded at times. The mountains start in NY and end at the Maine coast, so your whole trip will be steep.
I list my location as "Upstate" but that is a joke- on the streets of NYC, "to be upstate" means "to be in prison". I'm really only 90 minutes north of NYC. If you are that far south in NY, PM me for shower food place to crash etc.