From Stamford · Route 23 · Great Barrington to Blandford

Full-day version that starts in Stamford: it adds the ride there and back to Route 23 · Great Barrington to Blandford. Here is what you'll find on the core stretch:

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.