From the McGregor parking area, the trail climbs steep switchbacks to gain the ridge. After a little less than a mile the Hickory Hollow Loop branches off to the right, connecting eventually to the Point Ann Trail.
A "false summit" of sorts appears as the trail levels out for a few tenths of a mile, before making one last steep climb to gain the ridge properly. From there, gently rolling hills with minimal technical difficulty allow runners to pick up the pace. The trail follows right on the edge of the bluff, allowing spectacular views of the Mississippi to dominate the first half of this trail before the ridge meanders perpendicular to the Big River. The "overlook" portions are also dotted with mounds built by prehistoric Native Americans.
A few junctions with the Bluebird and Weeping Rock trails allow visitors to shorten or lengthen looped routes, respectively. Ignoring those junctions, the trail ends at the Homestead parking area.
Flora & Fauna
Sections of deep shade and steep cliffs give way to south-facing prairies, meaning this route runs the gamut of upland habitats. Expect spectacular plant diversity throughout the seasons. Bald Eagles and Turkey Vultures drift lazily along the cliffs, and Barred Owls cruise the woods even in daytime. Bobolink have been spotted on the prairie near Homestead.