Held at the renowned A.E. Backus Gallery and Museum—named after the influential mentor to many of the Highwaymen—this annual event features a dynamic display of original Highwaymen paintings, both vintage and new works. The Highwaymen Celebration Weekend offers visitors the rare opportunity to meet original members of the group and their second-generation successors, watch live painting sessions, and hear personal stories behind the iconic works. Guests can explore the ongoing legacy of these pioneering artists while enjoying a unique cultural experience rooted in community, creativity, and Florida's rich landscape heritage. With artwork available for purchase, the event also provides a special chance to own a piece of living history.