The Whippoorwill Award aims to bring attention to the theme of rural spaces and people in the larger genre of young adult literature. This award annually recognizes the best books for the middle grades and young adult readers that portray the value of rural spaces, knowledge, people, and cultures. The Whippoorwill Award is intended to be a resource for young readers, their teachers and other adults in their lives to help identify authentic, complex, meaningful, and well-written portrayals of rural life. This article discusses the third cycle of Whippoorwill Book Award winners, covering the publication years of 2020 and 2021. The winners include 13 diverse and compelling books that portray rural people and places in dynamic and energizing ways.