An Overland trip is both supportive and challenging. In an environment of caring and consideration, Overland's students are held to high standards of personal conduct in groups that live cooperatively and wholesomely. An Overland trip is noncompetitive but it is always challenging, and students can pick the level of challenge they desire. Easier trips include a bicycle trip on Cape Cod or a moderate hike in the Rockies. Overland trips are unusual in the manner in which they emphasize the need for cooperation and consideration from each group member.
Participants work together to set up camp, provide meals, and plan activities.
Leaders act as coaches to help instill a sense of independence and self-reliance in their group members. Students finish an Overland trip with a new feeling of confidence in their outdoor skills as well as in their own ability to meet new and challenging situations successfully. The combination of high-quality leadership, challenging itineraries, and working together in small groups makes Overland what it is today. Overland trips have had a profound effect on many alumni, who state that the trips are experiences they will never forget. The trip ends with a whale watch and sightseeing in Boston.