The Cowboy Up Trail in the HRCA Backcountry Wilderness is a short trail that runs between the Douglas County East-West Trail, and the Longhorn Ledge Trail. Cowboy Up offers great views to the West - the entire Front Range from Pike's Peak to Long's Peak can be easily seen from Cowboy Up, and the view to the south is into the scenic Perry Park area.
Cowboy Up is a fairly flat trail, traversing the west side of the Highlands Point mesa. Like all trails within the HRCA Highlands Ranch backcountry, access is limited to Highlands Ranch residents.