Local club cuesheets: www.freewheelers.org/cues.htm

A century ride in early September: www.amherstrotaryclub.org/covac/

I did the COVAC (Connecticut Valley Century) last year, and it was a very pleasant, well organized and supported event. Evidently there are plenty of cyclists in the area and no shortage of good places to ride, whether you like flat rides (the valley) or hills (everywhere else.)