Overland Summers

Our Story

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40 YEARS OF ADVENTURE

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.

Having just graduated from Williams College, Tom Costley was inspired to offer experiences to kids with a focus on small groups, carefully crafted challenges, and clearly defined goals. In 1984, Overland became a reality with three 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 world’s most beautiful mountains, work with an underserved community, master a new language.

Almost forty 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 Over The Years

OUR HISTORY

1982

Tom Costley bikes across the country and dreams of creating Overland.

1984

The first "catalog" is printed for $35 at a quick print shop.

1985

The first trips run: three groups explore New England. Away we go!

1986

Overland offers first hiking trips out West and abroad.

1991

Eight years in, decision time: Keep Overland going? Yes!

1992

Overland booms... Liz and Tom welcome Cate. A very good year.

1993

An Overland student, Amy Selinger, becomes an Overland leader.

1994

Liz and Tom welcome Luke. Another very good year.

Discover Overland

OUR STORY, SHAPED BY OUR COMMUNITY

Since Overland’s first (and only) trip in 1985, we have expanded across the globe, but our core values have never wavered. Hear how Overland came to be created and how it has grown to the organization it is today.

OVERLAND BY THE NUMBERS

We log hundreds of miles scouting new destinations and review thousands of applications, all in service of 1 goal: a summer full of friendship, fun, and adventure.

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students each summer

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trip leaders

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years running

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countries

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OUR LEADERS

Overland’s leaders are terrific role models for our students. Capable and caring, our leaders focus on creating supportive, wholesome environments where every student can flourish and grow.

our Leadership style ›

stories from overland

Explore Overland through the eyes of students whose lives we’ve touched, the leaders who nurtured their experiences, and the families that witnessed the growth and joy of an Overland summer.

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our values

At Overland, rock-solid values — teamwork and leadership, independence and self-reliance, discovery and inspiration — imbue an organization where the standards are high, the expectations clear, the tone adventurous.

our values ›