Traditions have been a very important part of the Oakland experience for both staff and students. Each morning during summer school, students and residential instructors gather around the flagpole for flag raising. Students look forward to twice-daily Popsicle breaks as well as Friday night movies under the stars. Additionally, the Plantation Dinner in celebration of the Fourth of July is much anticipated each year as is the newer tradition of a holiday carnival.
During the regular school year, a special Thanksgiving assembly is held in the Union Mills Church. Another special event is the annual Horse Holiday held in December. Both the regular school year and summer session have concluded for many years with a special recognition banquet. Students are acknowledged at this time for their academic and social achievements. Oakland also has a unique graduation at the end of the summer session in which graduating students are honored by teachers of their choice. Recognition is also central to the Outstanding Citizens program and weekly Star Lists that have been used for years to recognize top performing students.