Ride leaves from: Housatonic Meadows Campground
The Dudleytown loop is the perfect Halloween ride. The route takes you up three climbs that each get you as close as you are legally permitted to go to the abandoned (and according to some, haunted) ghost town of Dudleytown. In addition to those three climbs (Dark Entry Road, Dudleytown Road, and Bald Mountain), which are each beasts, the ride includes the formidable Dibble Hill Road and Great Hill Road, as well as a few other tough climbs. To make it even more difficult, take a left off of Rt. 7 onto Swaller Hill Road, a 1-mile dead-end 12% climb.