Day Trip #3: Dirt Roads Adventure
Warm up by taking Danby Mountain Road (off Route 30 just north of Dorset) about five miles. Turn right on Edmunds and then left on Keeler. Then turn right on the paved Danby-Pawlet Road and continue down hill into Danby.
In Danby, cross Route 7 and head east through Mt. Tabor on Brooklyn Road. The paved portion ends in less than a mile. You'll find at least ten miles of dirt roads that take you through the Peru Peak Wilderness and Green Mountain Forest toward Landgrove. Bring a road atlas. Follow the back roads (preferably Hapgood Pond Road) towards Peru. Then take South Road to Winhall Hollow Road to Bondville.
In Bondville, take the Stratton Mountain Access Road through the Stratton resort, and follow Mountain Road south to West Jamaica Road. Turn right at a T intersection on the Stratton-Arlington Road. That road becomes Kelly Stand Road, which takes you to East Kansas (yes, you're still in Vermont). In East Kansas, take the Kansas Road to East Arlington and continue to Route 7-A. Turn right and then take a quick left on Route 313.
Head west on Route 313 about three miles, and turn right on Sandgate Road. After about 2.5 miles, turn left on West Sandgate for about one mile. Then turn right on Rupert Road and continue about six miles into West Rupert. Turn right and continue about two miles to Pawlet Mountain Road, which branches off to your left. Continue to the end, which is in Pawlet. Turn right on Route 30 and continue down into Dorset.