Class of '33 Trail and down the old Williams College Ski Area is a 3.2 mile lightly trafficked loop trail located near Williamstown, Massachusetts that features a river and is only recommended for very experienced adventurers. The trail is primarily used for hiking, walking, nature trips, and birding and is accessible year-round. Dogs are also able to use this trail.
You can either hike this as an out and back or you can loop it a few different ways. You can loop it by coming down the old Williams College Ski run (3.17 miles) or by continuing up the Ski run where it meets up with the Taconic Crest Trail then down the Berlin Pass Trail (4.3 miles).
Some buddies and I accidently hiked this trail. We were intending to take an easy trail called the WRLF Loop and took a left towards Berlin Mt. when we should have taken a right towards the old Williams College Ski slope. This trail is rated double diamond for a reason. There were parts that were quite steep and the return trip down the old ski slope was challenging because of the pitch of the slope. The trail info says that it is a 1.2 hour hike but I can't imagine that happening. It took us at least three but then again two of us were over 50.