The original junior or community college in San Luis Obispo County was initiated as a postgraduate division of San Luis Obispo High School in 1916 and remained in operation until the United States entered into World War I. In 1936, the San Luis Obispo High School District again formed a junior college, which remained in operation until June 1959. 

On April 16, 1963, San Luis Obispo County voters approved the formation of a countywide junior college district, serving seven public high school districts. The newly-formed San Luis Obispo County Junior College District served the Arroyo Grande Union High School District, Atascadero Union High School District, Coast Joint Union High School District, Paso Robles Joint Union High School District, San Luis Obispo Union High School District, Shandon Joint Union School District and Templeton Union High School District. 

During the 1964-65 college year, the San Luis Obispo County Junior College District offered a limited evening division program with 463 students registering for the fall semester and 696 enrolling for the spring semester. Temporary quarters were established at Camp San Luis Obispo, a California National Guard facility located halfway between San Luis Obispo and Morro Bay. Classes and offices were situated in refurbished barracks, recreation rooms, and mess halls.

Despite the District’s modest beginnings, 917 day students and 991 evening students were enrolled in classes by the fall of 1965. Evening division classes also were conducted at three other locations in the county - Arroyo Grande, Atascadero, and Paso Robles. On October 4, 1965, the Board of Trustees of the San Luis Obispo County Junior College District named the new college “Cuesta College.” In 1971, the “junior” college district was renamed to “community college.” 

In 1970, ground was broken for the college’s first permanent buildings, located on a 150-acre campus west of Camp San Luis Obispo. During the following 40 years, classroom buildings, a library, observatory, student center, art and music lab building, art gallery, high tech learning center, children’s center, performing arts center, and office spaces were constructed on the San Luis Obispo campus. By spring 2012, the student population on the San Luis Obispo Campus decreased to 8,000 students due to severe reduction in state funding.

Cuesta College has a long history, which dates back to the late 1960s. It is a history of teaching at off-campus instructional sites. Through the years, Cuesta has taught in Cambria, Morro Bay, Atascadero, Shandon, Paso Robles, Templeton, Arroyo Grande, and Nipomo. 

In fall 1998, the college opened the North County Campus on its 105-acre site in Paso Robles. The campus, built almost exclusively with private gift support, has grown from 1,200 students the first semester to 3,000 day and evening students in spring 2012. The site began with modular buildings to be used until permanent buildings were approved by the state. In the summer of 2005, the first permanent building opened to students: The Fox Family Building. This building houses Allied Health, Math, and Science. The college broke ground for a second permanent building in spring 2010: The North County Campus Learning Resource Center. The Learning Resource Center was completed in fall 2011 and began serving students in spring 2012. The building was named in honor of donors Dale and Mary Schwartz and dedicated May 24, 2012. 

The South County Center is an off-campus evening instructional site at Arroyo Grande High School, provided in cooperation with the Lucia Mar Unified School District. During the spring 2012 semester, 600 evening students were served at this site. 

Cuesta College now serves more than 11,000 students at all college locations. The college has become a center for community use by individuals, families, and community groups on an extended-day and year-round basis.