This tour takes advantage of the fall foliage that most visitors to New England come to see, along with the countryside of white-steeple churches and red farmhouses. Along the way, it presents the opportunity to sample some of the simpler pleasures of the region—hot apple cider, tart cheddar cheese, and maple sugar candy.
After a stroll around downtown Boston  and bucolic Boston Common , get in the car and take a long drive down I-90, I-84, and Route 4 to the rolling hills of Litchfield  (2.5 hours) in the northwestern corner of Connecticut.
On your first day here, take an all-day tour of Litchfield’s scenic town common and the historical sites of this colonial-era town. The next day, take a driving tour of the orchards and town greens of the Litchfield Hills , cruising down leafy back roads and stopping in antiques shops  at will.
Drive north along Route 20 to Stockbridge  (1 hour), one of the most picturesque of all New England towns. While there, pay homage to small-town America with a visit to the Norman Rockwell Museum .
Drive east along I-90 and north along I-91 to the quaint southern Vermont town of Grafton  (2 hours), where you can stroll the picture-perfect town center and see cheddar made at the Grafton Village Cheese Company . Another day, take a drive around the surrounding small towns, including Weston, where the Vermont Country Store  is a trip back into an earlier era. Spend the night in a quaint country inn in the area.
Drive north along I-91 and west on Route 4 for a lunch stop on the delightful Main Street of Woodstock  (1 hour). Retracing your steps east on Route 4, stop for a hike down Quechee Gorge  as you make your way up I-91 to overnight at the college town of Hanover  (0.5 hour).