Not only does this rural route carry over a railroad bridge, it covers a stretch of Sleepy Hollow Road. Toss in some dirt back roads and a nice hilly vista and it doesn’t get more Berkshires than that! Another recommendation from Berkshire Sports, this route starts at the intersection of Dublin Road and Summit Road in Richmond. Start out heading south on Dublin Road, then take a left on Sleepy Hollow, continuing over the railroad tracks. From there, continue south on Dublin until you reach Swamp Road. You’ll only be on Swamp Road for a few moments, but it can be busy, so keep your head up until turning left on Stevens Glen Road. There is a good hill here, culminating in a four way intersection. Head straight through, north on Lenox Road, before turning right on East Road. After a steep and curvy hill, you’ll be rewarded with a spectacular view. Continue on East Road all the way to Sleepy Hollow Road. This will carry you all the way to the railroad bridge and back to Dublin. At 7.7 miles with hills, it’s a bit of a long one, but it’s a chance to experience rural New England at its finest.
Shorter Option: To save 2 miles, turn right at Lenox Rd. just after the 3 mile mark, to Dublin Rd. See route map.