I'm a couple of towns east of Winchester. The CT river is great for fishing. There are a lot of snowmobile trails in the area and hunting isn't bad either.
Looks like a I 91 commute. I've only driven it on my way to a hunting club in MA on the weekends. I can't imagine it would be a bad drive, hopefully someone with weekday experience will chime in.
Hope your move goes well, and I hope you ice fish.