I'll echo Mike Stumpf on Springfield, MA. It's a hell-hole, probably the worst city in Massachusetts and definitely the poorest. There are a lot of nice places in New England, though. I live in the Boston area, although I'm moving to Madison, Wisconsin this summer - Boston's a really nice place to live if you can forget the cost of living is so damn high.
You should visit Portland, ME. I grew up there and will probably move back some day. It's a nice small city, with lots of outdoor opportunities, some nice urban culture and only a two hour train ride/drive to Boston. Portsmouth, NH and Providence, RI are nice, too.