Route 23 · Great Barrington to Blandford

The Berkshires closest to New York: MA-23 leaves Great Barrington, passes Monterey and Lake Garfield, crosses Otis and East Otis and ends in Blandford. It's 25 miles of two-lane road that follows the hills at a good pace with easy curves, fine for a mixed pack. Fuel in Great Barrington, since there are few stations heading east. On weekends Great Barrington is busy on the way out. From Blandford, Route 23 chains with Jacob's Ladder.

Route 23 climbs out of Great Barrington, a town of restaurants and old storefronts, past Butternut ski area and into the hills of Monterey, a small village with Lake Garfield right by the road. Beartown State Forest, with Benedict Pond, is a short turn off the route between Great Barrington and Monterey. The forest covers more than 12,000 acres, and the Appalachian Trail runs through it.

East of Otis the road crosses higher, emptier country on the way to Blandford, which sits on a hilltop and holds an agricultural fair every Labor Day weekend, a tradition kept by a volunteer society founded in 1867. From Blandford you can link to US-20 and Jacob's Ladder, or head south on MA-8 from Otis toward Connecticut. Fuel up in Great Barrington, and in October expect leaf traffic in town.