Updated: Sep 10, 2019
Where St. Cloud Street in Rapid City ends, the eastern side of the Skyline Wilderness Area begins. Follow this residential South Dakota road until it stops at the gate to the wilderness area. This entrance is actually an access road to the park, and was supposedly the original road up to the amphitheater. Some of the old rock work is still visible as you climb the hill.
Follow the road up to the old amphitheater, which is located near the center of the wilderness area. From there, you can hop on a trail headed towards any part of the park.
Near the St. Cloud Entrance is trail marker SWA 364. This trail climbs the hillside, winding back and forth until it eventually runs into a fork at trail marker SWA 368. Taking a right will lead you in a loop back towards the amphitheater (which is a fun walk in and of itself).
Taking a left at the fork, however, leads deeper into the southeast part of the wilderness area. Bear left along the trails and you'll find a nice spot to overlook the city just above Palo Verde Drive.
This is a fun place to go hiking. It's quiet, and not as heavily trafficked as other parts of the Skyline Wilderness Area. You get views of downtown Rapid City from the eastern side of the park as you ascend through the forest.
These trails aren't too strenuous and make for a nice walk in the woods. The dogs absolutely love coming here. There is much to sniff and explore, and many trails to follow. Even on a chilly day we enjoy a hike here, as the trees tend to block out the wind. It's another great place to get out into the forest without ever actually leaving the city.