There's a lot of great riding around Springfeild. The city is on the Connecticut River, the valley of which runs all the way through Massachusetts and up into Vermont. There are a lot of nice, flat roads in the valley. You can also head into the Berkshire Hills to the west and find a lot of climbing, some of the climbs being pretty long (Rt 9 out of Northampton into Goshen, for example). Lots of good, quiet roads in the hills.
There are quite a few colleges with cycling teams in the area, and cyclists are a regular sight.
As for the winters, they can run the gamut from mild to bitterly cold. Here in new England, you never know what you're in for until it gets here. Last winter was one of the mildest on record, you could ride comfortably on the road all through the winter season. The winter before, however, was cold and snowy, forcing you to find alternative forms of excersize. During such winters you switch to skiing, snow shoeing, join a gym, do roller rides, etc.
Over the past few years, we've been getting more of the cold, snowy winters and fewer of the mild ones.
