Outdoor adventure education has an extensive history of considering how its students should wrestle with privilege. Recent events have brought issues of privilege to the forefront, which raises the question of whether outdoor adventure education can play a role in learning to see and affect systems of privilege. This paper examines several elements of outdoor adventure education that make it an ideal environment for teaching about systems of privilege, and makes the argument that Jack Mezirow's critical reflection, wherein people question the principles that underlie their ideas, should be a key element of outdoor adventure education curriculum in the 21st century. The authors' perspectives are grounded in critical theory and the assumption that power dynamics need to be examined in order to be changed. By combining critical reflection with the unique characteristics of outdoor adventure education, outdoor adventure educators may be able to successfully teach participants to recognize and impact systems that operate around them.