This is one of my favorite fall foliage day trips. Unbelievably, it passes through five (5) different states. It incorporates several interstate highways as a way of saving time, but primarily travels through a number of small towns and villages in New England. Obviously, the trip can be extended to involve several days, which will allow more and longer stops at several high points. The road trip as outlined below begins and ends in Rhode Island (my home) but, since it is a loop, it can be adapted to any starting point along its extent. The total mileage of this loop is approximately 315 miles. Allow a long, long day for the entire circuit.
Begin on Interstate 295 in Rhode Island and travel west on US Rte 6 to Rte 101 West (Scituate). Follow Rte 101 into Pomfret, CT, then take Rte 169 North through Pomfret village and Woodstock. Be sure to stop for a few moments to admire Roseland Cottage, along the way, and then continue into Massachusetts. In Southbridge, get onto Rte 131 North to Sturbridge, then north on I-84 to the Massachusetts Turnpike (I-90) heading west. Just past Springfield, take I-91 North as far a Deerfield. If time permits, stop in Deerfield Village, a very old New England community or at the Yankee Candle Store. Otherwise, travel west on Rte 2 (the Mohawk Trail), one of Massachusetts’ most scenic highways. Take a short detour to Shelburne Falls to see the Bridge of Flowers, then get back on Rte 2 West through North Adams (check out the famous panoramic overlook) and on to the lovely community of Williamstown, a quintessential college town. In Williamstown, turn north on Rte 7 into Vermont. In Bennington, stop for a few moments at Bennington Battle Monument and climb to the top for commanding views of the picturesque countryside. Then travel East on Rte 9 across Vermont and as far as Keene, New Hampshire, then take Rte 101 East toward Peterborough. Next take Rte 202 South through Jaffrey (perhaps stop in at the Monadnock Inn for dinner) and on into Massachusetts. In Winchendon, pick up Rte 140 South to I-190 South, then I-290 South to Worcester. In Worcester, take Rte 146 South back into Rhode Island and onto I-295, your starting point.