Since the nine-month school year became common in the United States during the 1880s, schoolteachers have never really had summers off. Administrators instructed them to rest, as well as to study and travel, in the interest of creating a compliant workforce. Teachers, however, adapted administrators’ directives to pursue their own version of professionalization and to ensure their financial well-being. Summers Off explores teachers’ summer experiences between the 1880s and 1930s in institutes and association meetings; sessions at teachers colleges, Black colleges, and prestigious universities; work for wages or their family; tourism in the U.S. and Europe; and activities intended to be restful. This heretofore untold history reveals how teachers utilized the geographical and psychological distance from the classroom that summer provided, to enhance not only their teaching skills but also their professional and intellectual independence, their membership in the middle class, and, in the cases of women and Black teachers, their defiance of gender and race hierarchies.