Cool Spirit Loop

The start of your hike will begin at the Boston Ballfield parking lot for the Great Allegheny Passage (GAP) Trail. You'll take the GAP toward Pittsburgh and after about a mile, you should be approaching the entrance to Dead Man's Hollow on the left. The GAP trail is a smooth and flat warmup for the hills to come. Once you enter the hollow on the Ruins Trail, you proceed up the trail until you reach a Y. Here, take the right fork to start on Dead Man's Loop, head over the bridge and continue up deeper into the hollow (going left will take you up the Witch Hazel Trail). After about three or four stream crossings, you'll arrive at another Y. Here the trail left stays on flat ground and ends in a few hundred feet. Take the right fork of the Y to begin your upward climb on the many switchbacks on Table Rock Trail. When you top out, you'll be at a T-intersection. This is the Cool Spirit Trail. You can do it either direction, and I know for a fact the trail is very well marked with blue diamonds with black arrows. Table Rock is down at your left, by the way. It's made of "siltstone" a soft, sedimentary rock that many people have carved their initials in over the years. I wouldn't suggesting doing that, but its interesting seeing things 30-50 years old carved there. Once you complete the Cool Spirit Trail just return the way you came to the GAP trail and back to your car. Unless you want to add an additional four miles to your hike then simply follow the previous directions and also hike the Witch Hazel Trail which would give you about a ten mile hike with about 1,500 feet of elevation gain.

My suggestion would be to read the Dead Man's Hollow website as there is a lot of interesting history here.