Originally Posted by plasma800
Driving through Connecticut is.... well ... hmmm... interesting.
Most people seem to go through the state on the interstates have no idea how pretty the state really is, particularly the northeast corner but the eastern half of the state including the shoreline villages are all very nice. You'll find the same scenery/views you find anywhere else in New England only less crowded. I'll agree with anyone about the interstates not being fun to drive but the back roads away from the larger cities are not that bad.
As others have mentioned, Acadia is a memorable place. Other places I can recommend in New England for scenery would be Maine south of Portland, the White Mountains, the Northeast Kingdom of Vermont and scenic routes in Vermont like Route 100, the Berkshires of Massachusetts.
If you like historical places, there is Old Sturbridge Village, Plimouth Village and a half dozen national historic park units covering everything from the Revolution to the Industrial Revolution. One is the Marsh Billings farm and Shelburne Farm in Vermont as you mentioned historical farms.
In eastern New York, there's West Point, Cooperstown area (many museums besides the hall of fame such as the Farmers Museum) and the Olympic sites and High Peaks surrounding Lake Placid.
In terms of routing, like I said if you avoid larger population centers, secondary highways move fine and you'll see a lot more scenery and places to visit than along the interstates.
You're going to miss our two biggest seasons fall foliage and maple sugaring but the further north you are, you might start to see some color in swampy areas by early September. Maple season is only in the spring but you can buy maple products year round (not that I know anything about that!).