The Skyline Trail began as a network of footpaths created by Oregon's indigenous tribes. Early fur traders and explorers followed in their steps, seeking safe routes over the unmapped Cascades. Judge John Breckenridge Waldo later spent decades exploring the mountain trail between Mount Hood and Crater Lake and led the campaign for the area's preservation. During the 1920s, the Forest Service briefly considered turning the path into a scenic highway and sent one of its first recreational specialists, Frederick Cleator, to blaze a prospective route through the mountains. But when the highway proved impractical, the Skyline was reinvented, becoming the foundation of America's greatest long-distance hiking trail.