The school was opened in 1987 in a trailer behind the Douglas County High School football stadium. One teacher, Mr. Charlie Glinch, was hired to teach all subjects to a class of eight students.
Two years later, the DCAP had grown to include 15 students and an additional teacher, Mrs. Cindy St. Vincent, also joined the expanded program. Classes were moved from the trailer to a classroom in DCHS, and were co-taught by Mr. Glinch and Mrs. St. Vincent in the morning. Students were expected to work in the afternoons, and were often visited at their job by their teachers. Over time, more students joined the program and additional staff members were hired to meet the growing need for alternative education. As more classrooms across the district were assigned to the program, it became increasingly obvious that the program would soon need to be consolidated at a central location. In March 1991, the old Swedish Medical Facility in the Silver Heights subdivision became the new home for the DCAP. That same school year, the DCAP saw its first graduating class of two students.
In October 1992, with five teachers and five administrative and supportive staff serving roughly 60 students, the DCAP became a self-sustaining school: Daniel C. Oakes Academy. That summer, the beginnings of an outdoor education program began with funding from the JTPA. Greg Simons took the first group of students out on Outward Bound programs and saw improvements in the students' academic achievements after participating in experiential learning. The Outward Bound programs continued the following summer, and in February 1994, the ideas of the program were incorporated into the school's curriculum. The first Outdoor Education trip was led by Greg Simons to Bent's Fort during spring break, and a second trip was led by Rick Young to explore Ute Mountain and Ute culture. Both of these excursions brought a tangible change to D.C. Oakes' culture, and a sense of family community began to emerge within the school. It was clear that the Outdoor Education program needed to continue.
The 1996-1997 school year coincided with many changes to the school that are still in place today - the school calendar was modified to the current year-round schedule, the word "Academy" was dropped from the school's name and replaced with "High School", and the Phoenix was adopted as the school mascot.
The continued expansion of the student body required the establishment of a secondary site in Parker and the relocation of the Castle Rock location to a larger building at 15 S. Gilbert Street. The Outdoor Education program had expanded over the years to include additional trips and was being funded by Drug Free Schools and other grants obtained by the staff until 2002, when enough funds were earmarked for the program in the school's budget.
In 2003, a permanent home was found for Daniel C. Oakes High School at 961 S. Plum Creek Boulevard when the current building was purchased and renovated by the district. The Parker and Castle Rock locations came together under the same roof in 2004 with over 130 students, 14 teachers, and 5 administrative and support staff.
The school maintains similar numbers today, and is proudly continuing the tradition of Outdoor Education.
