The curriculum at The Highland School is constantly evolving and changing. Depending on the amount and kind of interests, classes may be formed, independent studies begun, or community resources investigated. All classes and investigations are voluntary in keeping with our philosophy that each school member is responsible for his or her own learning. School members can pursue activities in as much depth as they desire, and are free to change endeavors as they see fit.

Much of The Highland School's curriculum is created through daily interactions between the students and staff. Full time internet access and low student/computer ratio enable school members to supplement the school's library resources. Activities are frequently interdisciplinary. For example, the Archeology Guild established a dig near the school to investigate a 19th Century homestead. Archeological activity (researching records in the courthouse, collecting relevant historical data from local periodicals and libraries, interviewing elderly local residents, mapping the site, studying archeology methodology, laying out, measuring and recording the areas to dig, describing, identifying, and cataloging artifacts found) incorporates the traditional subject areas of language arts, history, math, and science. Most learning at Highland, however, takes place informally - through sharing with others, watching someone more skilled at an activity, or experimenting with unfamiliar activities and experiencing their consequences. The wide range of areas explored during any one year attests to both the opportunities available at The Highland School and the eagerness of its members to pursue their interests.