I live in Florida now but I grew up in New York and I remember the winters. The hardest part was getting out of the driveway. A path to the driveway and the driveway had to be shoveled right down to the ground or pavement so my feet wouldn’t slide when I tried to pedal or stand (I am in a wheelchair). As long as the driveway was cleared I could get myself out to the road for an accessible bus with a lift and go out myself. When I had to get in and out of a car I would take a throw rug with a good latex backing to step on because parking lots aren’t plowed clear.
I was in a power chair for 3 years, have been out of it now since the summer of 2004. But when we went out (we live in northern MN, lots of snow), we would take my manual chair & my husband would push me, as I had no strength in my arms or hands. But my son is 29 & has been in a manual sports wheelchair all of his life. He works fulltime, drives with hand controls & manages to push himself wherever he needs to go. He is a sports writer, so he has to go out often to cover high school basketball, hockey & swim meets for both boys & girls. I still don’t know how he has done it all the past 7 years, but he does have great upper body strength. Look into public transportation, we have a program called Dial-arid which picks people up anywhere & transports them for $1.50.