The first parts of the Cockaponset Trail were built in 1934 as a Civilian Conservation Corps (CCC) project. The fruits of CCC labors can be seen on the northern parts of the trail. Look for excellent grading and enduring rockwork. Also, east of the trail just north of Jericho Road, you can see the footings of the old CCC-constructed Turkey Hill Observation Tower. The trail also passes several defunct charcoal production sites.

The idea is to climb Devil's Rest, Mt Defiance, and Dog Mtn.  Any route is allowed on these summits.  Time from the first TH to the last, and includes driving between the THs.  Otherwise, any route is allowed.  It comes to about 26.6 miles with 10,000+' of elevation gain.