There is no parking at the trailhead. Park at the Green in the town of Dorset, then ride out Church Street to the end of the street. Turn left onto Dorset West Road, ride approximately 150 feet and look for the trail entrance to Humphrey's Trail on the right. Stay on the main trail; the few trails that branch off are all private property.
Humphrey's Trail is a steady, tight, and sometimes steep climb on the way out. As you wind your way through the trees, you'll encounter several boardwalks, and a view of the town of Dorset on your way up. Once up the climb, you have the option to continue onto Bunker Loop
for some additional mileage, or you can turn around and head back down the way you came - be ready for a fast, flowy descent!