We stopped at Stockbridge, home of the Museum of Norman Rockwell. This picturesque burg is a great place to just wander and look. The Red Lion Inn is old and beautiful, and even if you're not staying the night there, you should try the little restaurant and pub for some food. It's great ambiance.
Another great stop on this trip is Mount Greylock. It's in North Adams, Mass, and it's the highest peak around. There is a road to the top, and when you get there you can climb the observation tower to get amazing views of the area. There's a snack bar, and plenty of hiking to keep you occupied.
Natural Bridge State Park is also in North Adams, and is a cute little park with a real natural bridge. I've been taken in by ads for natural bridges before and found them to be only in fantasy land a bridge, but this one is real. It is small, but it is real. The park is scenic and a great little stop along the way.
Brattleboro Vermont was really something in it's heyday as an outlet king. Today it's more of a hippie town. It's a great stop on a Columbus Day roadtrip though, and we took advantage of the lower hotel rates there. There are a lot of restaurants and shopping, but be prepared to pay more for healthy food, and green shopping. It is of note that author Archer Mayor, known locally for his mystery novels, lives and works as a forensics police officer in that city and some of his books take place there.
Some other things to look at in the area. You can always stop off at Yankee Candle Company's flagship store in Deerfield, MA. Also in Deerfield is Magic Wings Butterfly Sanctuary, Deerfield Zip Lining, and Historic Deerfield.
In Greenfield, MA there is Poet's Seat Tower, and the French King's Bridge.
In the Holyoke/Springfield, MA area there is the Holyoke Mall which is a different kind of mall from the norm. There is also Six Flags which has special attractions for Halloween. There are lots of museums, including a Dr. Suess Sculpture Garden and the Basketball Hall of Fame.
It's a wonderful trip to take with a lot of things to see. Don't miss the fall. It can be the best time of the year.