Adam: Where in Wisconsin?

...and where in Mass.?

Around Boston, you get less snow than inland and it doesn't get as bitter cold as inland or in the Berkshires.

Milwaukee's winters aren't too different in length from Boston's but it can get colder. Milwaukee and along the lake, you can get "lake effect" snow, but otherwise, most of the weather comes from the northwest and the "Alberta clipper" can bring bitter, bitter cold but perhaps less snow than you might be used to.

Inland from Milwaukee and north of it, the winter lasts maybe a little longer than in Boston, but not that much. Look at a map and note that Milwaukee isn't a lot further north than Boston. Green Bay, on the other hand, is quite far up there.

MM called it pretty well. I've lived in Wisconsin and Masachusetts. Northern Wisconsin gets quite cold. The parts of Wisconsin along Lake Michigan are actually a bit warmer than inland because of the lake effect, but the dampness makes it feel a little worse.
Since most people move to Milwaukee or Madison, you will have some days much colder than the Boston area, especially in Feb. The average days will be a bit colder. If you hate cold weather you may be a little bummed out. Most people would be able to handle the move though.
I did, and I loved Wisconsin. If you're from the Boston area you'll be pleasantly surprised what you get for the $$$.

November and March & April are unpleasant. Dec/Jan/Feb just clear cold..sometimes -30 F. Most cars are equipped with engine heaters. Outdoor sports are "super". Snowmobiles, XC and downhill skiing. Rib Mountain at Wausau is great. Ice fishing. Modern clothing has eliminated cold weather problems. Road conditions are usually safe. Enjoy!

George, you must be really bored. Why are you pulling up posts that are over a year old?