Australian musician, Grayson, hits the road to discover America along the historic Route 66. Beginning in Chicago, IL Grayson goes from gig to gig along the famed roadway in search of the American experience as he engages with the eccentric locals in bars, jazz clubs, opera houses, record stores, taco stands, gun ranges and living rooms of small town Western America. Along the way he discovers the undervalued history, arts and diverse cultures of each region, culminating in California with one finale performance at the end of the trail.