Trip Leader · Summer 2027

Lead small groups of students on outdoor adventures. Training begins June 13, 2027 in Williamstown; leaders depart August 9.

Overland asks for a written application, résumé, three references, and two rounds of interviews. Applicants must be at least 18, have completed at least one semester of college, and enjoy working with young people outdoors. A driver’s license is expected for most trips; exceptions apply to select programs.