Footwear for winter hiking in western Massachusetts?

REI can set you up with boots- but since you are not "from here", you're going to really want to experience a winter first. You could find yourself tramping through a foot of snow, or several- hiking tends to stop when the snow starts flying, and then it's on to snowmobiles, cross country skiing, and snowboarding. You can actually get stuck in deep snow, and need to be rescued. Be careful. And while you're shopping, get some Wintersilks silk long johns, whether you go hiking or not. You're definitely going to need them!

I'm an old school hiker that has done a lot of winter hiking in New England

My boot choice would be an all leather 8" medium weight ( about 3lbs per pair)

Gaiters are mandatory as are 2 pairs of sox ( a light liner sock and a ragg wool outer sock

Walk 2 miles and then try on your boots

http://www.ems.com/shoes/shoe-accessories/gaiters/

Eastern Mountain Sports is the traditional old school retailer in the area

If you're driving up from GA see if you can stop in and visit Campmor in Paramus NJ - nice people

New England trails tend to be rocky and steep and in winter breaking a leg bc of postholing is a real threat especially on downhill trips

We all have our favorite winter walking sticks ; Mine is a 85 cm ice axe bc I can put all of my weight on it

Depends on how much snow is on the ground. If a lot, which is possible, you want snow shoes. Trudging through deep snow is exhausting. If there isn't a lot snow you will want some flavor of water proof hiking shoe.

You need a waterproof hiking boot. Go to any outdoor outfitter like REI and they can show you options.