Overland Summers

About Overland Summers

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. Thirty-five 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.


Overland Summers Trip Leader

June 2021 Williamstown, MA
“By working for Overland Summers you get the amazing opportunity to travel to some beautiful places in the world and lead hiking and backpacking trips for middle schoolers through high schoolers. I fell in love with Overland because of the amazing community it builds. I have never been in a place with so many like-minded people around me. The memories you create during an overland summer are also unbeatable, something as small as cooking 40 grilled cheeses on a small camp stove in Rocky Mountain national park at sunset is something I will never forget. ”

Trip Leader

June 2019 - August 2019 Yosemite National Park, CA
“Very rewarding experience that taught me valuable leadership skills.”
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