Midland School is a small, co-ed, outdoor education, preparatory boarding school for grades 9 to 12 in Los Olivos, California. Midland was founded in 1932 by Kent School and Harvard graduate Paul Squibb. Squibb envisioned a small, rural community reliant on the work of its inhabitants to meet its basic needs. Squibb and his wife, Louise, founded Midland in the midst of the Great Depression, believing that the essentials of education are a student, a teacher, and an idea.

Los Olivos is an unincorporated community in the Santa Ynez Valley of Santa Barbara County, California, United States. Tourism is popular in this rural area which is an agricultural region with an emphasis on wine grapes. For statistical purposes, the United States Census Bureau has defined Los Olivos as a census-designated place (CDP). The population was 1,132 at the 2010 census. The ZIP Code is 93441, and the community is within the area code 805.