New Hampshire and Vermont do a great job of keeping their roads clear. In the heart of a storm it can be treacherous, but they get the roads clear very quickly once the storm ends.
The food in general in Brat is not spectacular. I've enjoyed the Blue Moose Bistro. Whetstone Station is decent (but not great) for a casual meal. Brattleburger is good for a better-than-fast-food burger and fries. Mocha Joe is the local coffee joint, and is decent. The Brattleboro Food Co-op has a great beer selection, decent wines, and a good selection of other local food and craft products.
In Putney, VT, the next town north of Brat, the Gleanery offers the best food I've found in the area, Hidden Springs Maple has a great selection of maple syrups of differing grades (which I believe you can sample before you buy), and the Putney Food Co-op, although much smaller than the Brat Food Co-op, is perhaps even funkier and more interesting. They also offer decent sandwiches to go or to eat at one of their couple of tables.