The 20 Most Challenging Hikes in America, Ranked

4.Chicago Basin, Weminuche Wilderness, Colorado

Difficulty: Class 4

The Chicago Basin in Colorado’s Weminuche Wilderness is a mountaineering challenge, offering the opportunity to summit three of Colorado’s iconic Fourteeners: Mt. Eolus, Sunlight Peak, and Windom Peak. This 24-mile, three-day trek begins with a scenic train ride on Durango’s narrow-gauge railroad to the Needle Creek trailhead, followed by a journey through picturesque valleys and rugged peaks.

While the hike itself is moderate, summiting the peaks requires skill, with over 10,000 feet of elevation change and obstacles such as class 4 scrambles and narrow ridges. This adventure is a true test of endurance and mountaineering expertise. Trailhead at Needle Creek, best from July to September, accessible via Durango and Silverton Narrow Gauge Railroad, no permit required. It’s an incredible challenge for those seeking to conquer Colorado’s stunning Fourteeners.