Hello,
I've got a question for all you New England folks...I'm going to be taking a daytrip to the Berkshires in October (probably a Saturday, to be specific). What are the do-not-miss locations of this region? I was anticipating finding a couple of not-extreme hiking trails that had really nice overlook views (looking for a nice walk, not a survival test, here).

Scenic drives would be good too, as would be places to eat that are different, and fairly reasonable.
For reference, my friends and I will be driving from Framingham, MA, and returning there for the night after our trip. We were anticipating a solid 2 hours trip each way.