The program has been in existence since the fall of 1980, and was directed by a half-time coordinator. One or two programs a month were offered. The number of trip offerings increased dramatically during the 1980s (See Outdoor Program folders in the SWEBOP office.) In 1988-1989, the position was made into a 3/4 time Outdoor Coordinator and 1/4 time Resident Coordinator for 9 months. In 1996, the position became the Director of Outdoor Programs and was full time for 10 months. The need for this expansion is documented in the Sweet Briar Outdoor Program Proposal written in the spring of 1996, by the coordinator. As part of the reorganization of Co-Curricular Life the Director of Outdoor Programs position became full-time for 12 months in 1998. The program streamlined its activities into four programmatic areas: backpacking, hiking, caving, and rock climbing in 1998, as a response to co-curricular life’s in-house assessments. (See CC-Life folder.)

In the fall of 1997, a major initiative of the Outdoor Program was to create a common experience for all first-year students that helped connect them with each other and the land. In the spring of 1997, the college listed, as a strategic initiative, the need to use its land as a larger part of the learning experience, and the five-hour orientation program was created in response to that document. That year the Outdoor Program worked with North Carolina Outward Bound to lead the orientation program on the land. In 1998, the Outdoor Program called the experience "Learning on the Land" and used resources within the college to lead the program. The program continues to this day. (See CC-Life Binder and Learning on the Land folders with evaluations.)

In 1985, a leadership program within the Outdoor Program was developed. (See Outdoor Program 1985-86 folder.) The leadership program expanded in 1995-1996, when formalized training was established, and it was called the SWEBOP Instructor Program. The development of the leadership program at this time was a result of one-on-one meetings between the coordinator and her supervisor. A lack of quality training for leaders at the time was identified. (See CC-Life Folder and 1995-96 SWEBOP schedule.) In 1999, the Director of Outdoor Programs, in collaboration with the Director of Residence Life, developed a leadership training program based on the training for the SWEBOP Instructors and instituted it for all student leaders. Also in 1999, the two directors collaborated to create a student leadership conference. Once again the need for quality leadership training for all leaders was assessed in one-on one meetings with the Dean of Co-Curricular Life and discussed in the Director’s Meetings (See CC-Life folder, One-on One meetings with the Dean, Director Meeting minutes.)