Take a trip to 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/
Stay at one of the charming B&Bs in the area
http://www.stockbridgechamber.org/where_to_stay.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 cheddar 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.vermontvacation.com/
Drive through the Green Mountains on VT Route 9 towards Brattleboro (I-91 South). 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
Then head to Boston. Walk the Freedom Trail in Boston. It takes you everywhere you want to go, including the North End, which has the best Italian food in the country. The gelato is to die for. Other stops include Paul Revere's house, the Old North Church, Faneuil Hall, Old Ironsides (U.S.S. Constitution), and Bunker Hill. The tour of U.S.S. Constitution is really neat. Faneuil Hall is where everyone goes to meet, shop, and hang out. (Lots of street theater and other interesting things.)
http://www.aviewoncities.com/boston/freedomtrail.htm
The Museum of Fine Arts has a great collection
http://www.mfa.org/
There is a real interesting museum at Harvard. They have a botanical collection reproduced in hand blown glass. There are 3,000 hand blown glass flowers and plants. It's pretty amazing. Take a walk around the campus and Harvard Square.
http://www.hmnh.harvard.edu/on_exhibit/the_glass_flowers.html
For seafood go to one of the many Legal Seafood locations.
http://shop.legalseafoods.com/?source=google&page=homepage/pd/1
Go to a Red Sox game at Fenway Park.
Boston cream pie and Parker House rolls were created at The Parker House Hotel. Stop by for dinner. BTW you can order dinner rolls to go and they sell slices of the pie in the gift shop.
http://www.omnihotels.com/FindAHotel/BostonParkerHouse.aspx