The Shawnee Hills Wine Trail is an AVA region in Southern Illinois that is an undiscovered attraction with untapped potential in viticulture and winemaking. This case study aims to discover the most notable features of this wine-growing region and how its wineries can be improved to enhance quality and notoriety. To address these issues, the 12 wineries on the trail were visited, surveys were distributed to customers (n = 109), and extended oral history interviews were conducted with owners or representatives of the wineries (n = 9). Results show that the primary motivations for customer consumption of wine are social experience and relaxation. Surveys and interviews reveal that the natural beauty of the area enhances relaxation and that the welcoming atmosphere enhances socializing. It is perceived that wineries can be improved by decreasing incidence of intoxication, which is possible by customer education to enhance appreciation of complex varietals over sweet, overly palatable wines. This strategy will increase popularity and production of complex, quality varietals that are worthy of international attention.