After surviving Covid, Sherwood's lesson was clear: stop delaying things that make you happy. So he decided to head to the Pacific Northwest to hike. The Timberline Trail is an iconic trail circumnavigating Mount Hood in northern Oregon. Packed with incredible scenery, the journey cuts through gorgeous forests, across volcanic terrain, through glacier-carved canyons and ice-cold stream crossings, along alpine meadows, and under thundering waterfalls while providing unprecedented views of Mount Hood and the surrounding Cascade Range volcanic peaks. This is the story of a 4-day backpacking trip on the Timberline - the day-to-day experience, the highs and the lows, and the awe-inspiring beauty. An account of all 43 miles of this amazing, epic trail that will test you, humble you, and make you feel alive. The book includes hiking tips and backpacking lessons and stories from other mountains and hikes in the Western United States, including the Pacific Crest Trail and San Jacinto Peak.