In middle school, Waldorf students are encouraged to take on more responsibilities and develop greater independence in their learning and personal lives, preparing them for high school and beyond. Middle school students are invited to be stewards of the school. They are encouraged to reach out to others by playing team sports, producing the school-wide Michaelmas Festival, and working one-on-one with second graders in reading.

At Charlottesville Waldorf School, special consideration is given to the social and learning needs of students at each stage of development. For young adolescents in the middle school program, curriculum directs students to begin thinking critically and objectively through observation and refined lesson blocks including, but not limited to, algebra, physics, geology, astronomy, chemistry, geography, and world history. They are provided a supportive  environment to express themselves artistically with increasingly complex handwork, creative writing, woodworking, choir, and orchestra. In the Middle School, students begin technology class that centers on healthy and creative use of technology.