Cloud Cap Inn stands at nearly 6,000 feet on Mount Hood's northeastern flank. Built in 1889, the one-story, crescent-shaped, log-and-shake inn was the mountain's first permanent resort.

Portlanders William M. Ladd, a banker, and Charles Erskine Scott Wood, an attorney and writer, enlisted architect William Whidden to design the approximately 3,500-square-foot inn. They hired Chinese laborers to improve a wagon road up the mountain and started a stagecoach company to transport guests. Hood River men cut the lumber and built the inn, named by Wood's wife, Nanny. In its heyday, Cloud Cap featured fine dining, flush toilets, room to sleep thirty guests, and a gasp-worthy view of the 11,239-foot summit.

In 1891, Ladd and Wood turned the inn's operation over to James L. and Sarah Langille, who gave it a homier feel and added telephone service. They ran Cloud Cap for sixteen years, until their nephew, Horace Mecklem, took over. Homer Rogers, a Parkdale innkeeper, bought Cloud Cap in 1919. He sold it to Cascade Development Corporation. With a loop highway planned for Mount Hood, the developers envisioned a lavish, enlarged hotel and a tram to the summit. The Great Depression dashed that dream, and once Timberline Lodge was built in 1935, Cloud Cap could not compete.

The U.S. Forest Service paid $2,000 for the inn in 1940, but it fell into disrepair and closed in 1946. The agency planned to raze Cloud Cap, but in the 1950s, the Crag Rats mountain-rescue group negotiated to maintain it if they could use Cloud Cap for snow surveys, rescue operations, and outings, as they do still. Since 1999, the Crag Rats have coordinated extensive renovations in an effort to preserve Cloud Cap. The inn is closed to the public, although periodically the Crag Rats or U.S. Forest Service offer tours.