Somerville, MA (about 4-5 miles from Boston)
The good
1. In Somerville, Cambridge, reasonable attention paid to cyclists when planning. Also excellent for walking
2. Outside areas (Concord, Befdford, Littleton, Arlington, Carlisle), good roads for riding. You can spend forever exploring them.
3. Lots of cyclists and lots of group rides.
4. The Minuteman trail (if I don't want to deal with traffic getting to Bedford, I can ride 11 miles on this and be in much lower traffic areas.
5. Commuter rail,if you don't feel like driving you can take the commuter rail with your bike to some amazing riding further out.
The bad
1. Boston drivers (hyper-aggressive, rude, inattentive, unpredictable), seems to get better the further you move away from Boston
2. The occasional psychotic or homicidal driver (few and far in between).
3. Winter, winter, winter
4. Unfriendly cyclists (sometimes), could be the New England 'reserved thing'.
I like where I live because it is closer to Boston and Cambridge (I have a 3 mile commute). I don't like it so much for riding because I have to fight urban roads or take the bike path to really nice riding. However, considering what people post about their areas, if you can deal with the drivers, this place is not too shabby. I used to live near the Massachusetts NH Border and the riding up there was insane! I could be out of my house and in rolling farmlands in about 10 seconds flat. I once got a flat and almost every car stopped to make sure I was okay (that ain't happening anywhere near Boston).
So yeah, this area would be perfect if it wasn't for the damn drivers
