Seeking escape from his stalled relationship and unhappy place in the world, James, a recently pink-slipped music teacher, sets out to hike Kentucky’s arduous Sheltowee Trace Trail. Ignoring his girlfriend Joan’s plea to stay in Louisville and look for work, James sets out on his two-month journey in hopes of discovering the source of his restless dissatisfaction.
For a time, the lush but unforgiving terrain offers James a short-lived respite. But just as he adjusts to the quiet rhythm of life on the Sheltowee—making camp, serenading the open woods, ignoring Joan’s frequent phone calls—the trail rejoins with civilization, abruptly spilling out onto a paved road. Toting his fiddle, James is offered a ride to a community barn dance taking place near the next trailhead. Though he knows he should get back to the trail before nightfall, a local girl leads him astray. In the morning, realizing he’s low on supplies, James tries in vain to brush aside his guilt and navigate the trail towards town before dark. However, a pot-smoking, philosophical Park Ranger has other ideas.
In his haste to reach town, James sprains his ankle and winds up stranded with Lyman and Bo, a gregarious father and son duo. Eager for James’ companionship, the two have spent their summer alone in a tiny camper after being left by Lyman’s wife. With his meditative journey bombarded by the social pair, James reluctantly calls Joan and asks her to meet him at a nearby motel. Lyman happily offers James a ride into town, but first he wants to drop by an Appalachian Heavy Metal concert where he hopes to make amends with his estranged wife.
While Joan waits alone by the motel poolside, James finds himself entangled in Lyman and Bo’s family saga. Eventually a fight breaks out and James must choose between taking care of himself and reaching out to his new friends. Set among the verdant hills of Appalachia, PILGRIM SONG is a Southern Odyssey that leads James away from isolation through a labyrinth of strange characters who help him discover what he’s been missing.