Some highlights during my visit to the Berkshires in the autumn of 2010:
The Cascade (map): Trail head begins at the end of a very suburban road. Very limited street parking (think 2-3 spaces, depending on the skills of the driver). A short hike takes you over a nice wooden bridge as well as a fallen log-bridge. The waterfalls drops into a shallow pool at the trail.
Mount Greylock summit (map): The foliage on Mount Greylock was past-peak when we were there. Yet the view from the summit was still to-die-for. Climb to the top of the memorial for an even better look. The tower features a lighthouse beacon originally intended for Boston Harbor, but which somehow ended up atop a mountain.
Lenox: Home to Tanglewood and beautiful drives under the arbor of giant trees.