The 20 Most Challenging Hikes in America, Ranked

15. Timberline Trail – Mount Hood Wilderness, Oregon

Difficulty: Class 2

The Timberline Trail is a legendary 40-mile loop that encircles Mount Hood, offering breathtaking views of Mount Hood, Mount Rainier, and Mount St. Helens. Beginning at Timberline Lodge, this trail winds through alpine meadows, volcanic landscapes, and cascading waterfalls, making it a dream trek for seasoned hikers. With over 9,000 feet of elevation gain, the route typically takes about four days to complete, requiring endurance and careful preparation.

Must-see spots include Ramona Falls, Bald Mountain, and Paradise Park. Hikers should be prepared for river crossings, unpredictable weather, and some of the most rewarding scenery in the Pacific Northwest. Open year-round, this trail is ideal for adventurous backpackers looking to immerse themselves in the rugged beauty of Mount Hood.