Nine-year-old Jessie Hasting and her best friend, Ginny O'Connor do everything together, including starting fourth grade.

As the friends enter another magical year in elementary school, the girls soon realize that with more freedom comes more responsibility. While they focus on acting their age and being good examples for younger students, Jessie and Ginny memorize time tables, go on field trips, and learn about other cultures and traditions, eventually discovering that although growing up can sometimes be disappointing and lined with near disasters, it is always an adventure.

Jessie's Magical Year is the story of the misadventures and adventures of two best friends as they learn valuable life lessons while attending fourth grade.