Highland Creek Trail is an 8.6-mile one-way route from NPS 5 south to the Wind Cave Canyon junction. It is the park’s longest and most varied trail, crossing open prairie, ponderosa hillsides and wooded creek bottoms. The National Park Service calls it moderately strenuous; allow about five to six hours for the trail itself. This is a through-hike, not a loop. Arrange a pickup near the south end, or walk another 1.1 miles down Wind Cave Canyon Trail to its trailhead. With one car, hiking back to NPS 5 makes a 17.2-mile day before any extra connector.
The variety is the payoff, but much of the route is open and exposed. Choose it for a full backcountry day, not a shaded stroll or a short loop. The mapped 8.6 miles end at the canyon junction; the 1.1-mile walk to the Wind Cave Canyon trailhead is separate.