Trail No. 37 begins on the north side of Road 040 approximately 0.25 mile northwest of the junction with Road 8810. The trail starts climbing right away through a dense second-growth forest. After 1 mile of continuous grade, the trail levels out near the ridge top. The second-growth setting changes to old-growth Douglas fir and mountain hemlock. The trail reaches the base of the rock outcrop known as Sleeping Beauty. The formation was named because the profile somewhat resembles that of a sleeping woman. The formation is actually andesitic magma that intruded up into older volcanic rocks more than 25 million years ago. The andesite was exposed as the rocks eroded away.

The trail zigzags over bare rock to the old fire lookout site. Rock work in the walls along this section was done by the Civilian Conservation Corps in the 1930s. The crest is around 750 feet long, but is only 15 to 30 feet in places, with sheer drop-offs on all sides. You can still see the eye bolts that once served as anchor points for the lookout. From this vantage point, you can see the entire section of the Cascade Crest that runs through Indian Heaven Wilderness.

The lookout was built in 1929 on top of the 4,907-foot-high Sleeping Beauty peak. During construction, the sleeping woman's nose was blasted off to make a flat perch for the lookout. The lookout became her replacement nose until it was destroyed in the 1970s.

Sleeping Beauty Mountain, old lookout site, rock work, Lemei Rock and Red, Bird, and Sawtooth Mountains. Mountain goats are commonly seen in this area.