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.

Our History

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, serve an impoverished community, master a new language.

33 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.

The Overland Difference

  • Small Groups

    All of our groups are limited to 12 students, and each group has two leaders (one male and one female). When building our groups, we pay attention to age, grade, gender ratio and the mix of hometowns and schools.

  • Exceptional Leaders

    Far more than simply counselors, Overland’s leaders are role models of the highest caliber. Charismatic and accomplished, our leaders focus on creating wholesome environments where our students can flourish.

  • Student Ownership

    An Overland trip is guided by our leaders but driven by our students. With their leaders’ support, our students capably manage much of the work on the trip. Sharing daily tasks creates spirited, close-working groups where everyone contributes.

  • Careful Admissions

    Our admissions team carefully evaluates every application, always looking for students who are eager for the opportunities we offer. Our goal is to put together groups where each individual can thrive in a warm and caring environment.

  • The Group First

    At Overland, the group always comes first. By valuing teamwork, students learn critical leadership skills. Simple things, like waiting for each other at meals or thanking a fellow group member, lead to important lessons that stretch far beyond the boundaries of the summer.

  • Appropriate Challenges

    Every Overland program is a set of carefully crafted challenges with clearly defined goals: bike a coast, hike a mountain, serve a community, learn a language. The challenges are thoughtfully calibrated and the goal is always to have fun and make friends along the way.

  • High Expectations

    We expect a lot of our students—from playing by the rules, to helping out and having a positive attitude. The obvious is prohibited—smoking, drinking and drugs—but more than that, we strive to create wholesome and enthusiastic groups where students feel welcomed and valued.

  • Phone & Internet Free

    Overland students leave their phones and electronics at home—for the time that they’re with us they are fully engaged with their group and their trip.

Our Commitments

Our Team

  • 30
    Years of Experience

    Tom Costley founded Overland in 1984. Since then, we have grown to offer 51 programs worldwide, but remain true to our mission and values.

    Meet our Directors
  • 300
    Days of Anticipation

    Our first students sign up in August. Our admissions and enrollment teams work through the fall and winter to place over 2,000 students on trips.

    Meet our Admissions Team
  • 30,000

    Eight logistics coordinators—recent grads and past leaders—plan our 51 programs. Together, they have spent nearly 30,000 hours in the field leading for Overland.

    Meet our Logistics Team