Most of the pioneering studies related to wineries were conducted in famous wine regions, the results of which were not especially applicable to the small and emerging wineries in the United States. These wineries rely heavily on visitors’ on-site purchases; this highlights the importance of understanding winery visitors’ behaviors. This study explored the sequential relationships among winery visitors’ pre-trip characteristics (motivation, wine involvement), on-site experiences (perceived value), and post-trip evaluations (satisfaction, place attachment, winery loyalty). Intercepted winery visitors provided their e-mail addresses and were sent an online survey. Partial-least-squares structural equation modeling results showed that leisure-motivated and low wine-involved visitors perceive more diverse values in their winery experiences. Visitors’ perceived services, social benefits, and wine-quality values contributed to the positive post-trip evaluations. Winery owners stand to benefit from this research by being able to design winery experiences that are highly valued. Limitations are discussed and future research is suggested.