Climbing and Riding in New England and Beyond

Dudleytown Loop

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.

Hill NameLoc.DistanceAvg.MaxGainBRENTACOLCompare
Bald Mountain RoadCT1.1 KM12.525.2134.3340
Dark Entry RoadCT1.3 KM9.622.9122.2405
Dibble Hill RoadCT1.5 KM10.119.9151.8380
Dudleytown RoadCT1.3 KM8.625.6111.7292
Everest Hill RoadCT0.8 KM8.418.573.1156
Flat Rocks RoadCT1.8 KM6.711.6119.1158
Great Hill RoadCT1.6 KM9.114.3149.2304
Music Mountain/Cream HillCT4.2 KM5.912.4246.2399
Seeley RoadCT0.9 KM5.28.645.449