I am from missouri and go to school about 90min north of columbia, MO (where mizzou is). IMO it is a great cycling town with 3 solid bike shops and a pretty decent college team. Columbia was recently awarded some sort of national award for being an eco friendly/bike town. There are tons of people who ride in columbia. Also there are some good trails out there. The bar scene is awesome. The girls are incredibly attractive. What else could you want in a college town?!...Good bars! Hot Girls! And most importantly, plenty of places to enjoy on two wheels. Can't comment on Boston...never been.
~Nick