The best drive I think is to go out Route 2, there's tons of conservation land all around it, a bunch of parks and reservations (including Walden Pond and Wachusett) to stop and hike/ walk around at along the way.
Another option is to take the Mass Pike out west, then just after 290, get to Route 20 and then west. Route 20 is the old highway that ran east - west through the state before they built the Pike, so it goes through all the same gorgeous Berkshire hills, just at a slower speed so you can actually enjoy the view. Along 20 or just a quick drive from it, there are several orchards that still have apples to pick. You'll also pass by Northampton, MA which is a great university town, perfect place to get lunch or dinner. And if you drive all the way out to the NY border, Furnace Brook Winery has great wine and they're also an orchard.
If you want to see leaves minus a car, there are a couple of options. One quick option is to just take the commuter rail out to Worcester. Enjoy the view along the way and once you're in Worcester, you can wander around town and have some lunch, and hop a train back.
For a bit longer trip, the Amtrak Lakeshore Limited is a daily train leaving from South Station. If you get off at Pittsfield, you can spend some time in town, get a cab to a B&B in the hills, enjoy. Or you can go to Albany and transfer to the Ethan Allen Express and go all the way up to Rutland, VT for a beautiful weekend.
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