Our Story

For over 30 years, Overland has been more than simply a summer experience—it’s a life experience with value and resonance that extends far beyond the boundaries of a single summer. In everything we do, we seek to show our students how beautiful and exciting, how full of promise the world is.

Overland was a dream born on a cross-country bike trip in 1982.

Having just graduated from Williams College, Tom Costley rode across the U.S. and was inspired to offer experiences to kids with a focus on what made his trip remarkable: a small group, a carefully crafted challenge and a clear goal.

In 1984, Overland became a reality with three bike trips in New England. In the decades that followed, new destinations and activities were added but a common mission remained: to provide young people the chance to work together in small groups to accomplish something of importance to them—hike the Alps, work with an underserved community, master a new language.

35 summers later, Overland has grown wonderfully but remains true to its original inspiration. Rock-solid values—teamwork and selflessness—imbue an organization where the standards are high, the expectations clear, the tone adventurous.