This book traces Dahlman's 2013 trek over the 275-mile trail from Sycamore Shoals, near Elizabethton, Tennessee, to Fort Boonesborough, Kentucky. Initially undertaken after the death of his wife, Dahlman's account interweaves the history of the places he traverses with personal reflections and dozens of profiles and conversations with people he meets along the way. He questions how the Wilderness Road devolved from an important early American route predating Lewis and Clark to the humble footpath, both paved and wild, that now meanders through Southern Appalachia.