For the hilliest ride you could ever imagine, ride north on 202 out of Belchertown, along the west side of the Quabbin. Take the left turn that brings you up a killer hill into the center of Shutesbury. What makes it all worth it is following the road on the west side of the town, as it snakes it's way back down towards the U-Mass campus. Pick up Pelham road back to Rt. 202 and back home again! Close to 40 miles...here's one option!
http://www.gmap-pedometer.com/?r=2094330