Take day or overnight trip to Western Massachusetts and Vermont. The drive on the Mass. Turnpike (I-90) takes you through the rolling hills of the Berkshire Mountains and is very colorful. Head to the Norman Rockwell Museum. It's in the artist community of Stockbridge. It sits on an large estate and has some great views of the surrounding countryside.
http://www.nrm.org/
http://images.google.com/images?sourceid=navclient&rlz=1T4HPIA_enUS314US314&q=berkshire+mountains&um=1&ie=UTF-8&ei=bAVzSprFMIvQsQPX46D1CA&sa=X&oi=image_result_group&ct=title&resnum=4
If you wish, spend the night at a local Bed & Breakfast.
http://www.lanierbb.com/stockbridge-massachusetts-bed-breakfast.html
From Stockbridge, head north to Vermont on the Ethan Allen Highway, U.S. Route 7. to Bennington. They have covered bridges and great scenery. Stop at one of the many apple orchards for some fresh baked apple pie and cider. Don't forget to buy some world famous Vermont maple syrup and chedder cheese.
http://maps.google.com/maps?f=s&ie=UTF8&ll=42.8737,-73.151093&spn=0.185685,0.220757&t=h&z=12
http://www.bennington.com/
http://images.google.com/images?sourceid=navclient&rlz=1T4HPIA_enUS314US314&q=vermont+covered+bridges&um=1&ie=UTF-8&ei=GQNzSszRBo2MtAP0wpXZCA&sa=X&oi=image_result_group&ct=title&resnum=4
http://www.vermontvacation.com/
Drive through the Green Mountains on VT Route 9 towards Brattleboro (I-91 South) and then back to Boston via the Mass. Turnpike (I-90). There are several mountain lookouts to stop at to view the area.
http://maps.google.com/maps?f=s&ie=UTF8&t=h&ll=42.885776,-73.055305&spn=0.185649,0.220757&z=12
Here is the foliage forcast for 2009
http://www.foliage-vermont.com/