In this article, the authors discuss how incorporating traveling sketchbooks into their preservice art education and high school classrooms allowed students' situated knowledge to cross the boundaries of age and location. They begin with an overview of the evolution of sketchbook use in art education and the emergence of traveling sketchbooks. Then they explain how cross-generational traveling sketchbooks facilitated meaningful learning experiences that were academically rigorous, socially relevant, and personally fulfilling for both student groups involved.