In January 2008, Pinegar traveled from his home in Orem, Utah, to Hawaii for a vacation, renting an apartment on Kauai. He stayed in regular contact with his family via phone, with the last conversation occurring on March 24, 2008. During this call, he mentioned planning one last hike before returning home for a family event. He has not been seen since. After his disappearance, another hiker discovered Pinegar’s abandoned campsite in the Kalalau Valley, about five miles from the trailhead. His personal belongings, including clothing, camping gear, and an iPod, were left behind, but his wallet, phone, cash, and backpack were missing. The Kalalau Trail is known for its dangerous terrain and weather conditions, requiring the most rescues of any trail on Kauai, with over 100 fatalities. Pinegar was familiar with the trail, having hiked it several times before.