Overland Summers



Summer Trip Leaders


Our mission is to offer carefully crafted and superbly led trips that catalyze an understanding in students of the world beyond themselves, beyond their own needs and wants, and inspire them to see how beautiful and exciting, how full of promise the world is. Trips are offered across the U.S. and abroad, including Canada, Europe, Central and South America, Iceland, Norway and Tanzania.

Imagine a summer of adventure, commitment and community.

46 itineraries, 16 countries, 4 continents: that’s a lot of adventure. But leading at Overland isn’t really about where you go, and in some important ways, it’s not really about what you do. Instead, leading for Overland is about the people who surround you—the dynamic leaders you work with and the great kids you lead—and the many challenges, both big and small, that you tackle together.

Overland leaders are far more than simply counselors or guides. Our leaders are terrific role models for students. Charismatic and accomplished, leaders focus on creating supportive, wholesome environments where every student can flourish and grow.

An Overland leader’s commitments are many, but nothing is as important as your co-leader and your kids. No matter where you are, no matter what you’re doing, your most important commitment is the health and well-being of your co-leader and your kids. This commitment drives and informs your leadership every moment of every day.

The Overland community is supportive and wholesome. In all we do, we seek to create a culture of respect. We welcome students and leaders from across the country and around the world, we seek to offer broad access to our trips through our Open Arms financial aid program, and we value a range of life experiences and perspectives in our leadership staff. Overland aims to build a supportive and wholesome team of leaders, considers applications from all people and does not discriminate on the basis of race, color, national or ethnic origin, familial status, genetics, ancestry, religion, disability, sex, sexual orientation, gender identity and expression, or any other characteristic protected under applicable federal or state law. These values have been a part of Overland for over three decades, and they’re important qualities that we look for when choosing new leaders.

Overland leaders stay connected in a vibrant community that stretches beyond the summer, beyond leading. For over 35 years, Overland leaders have stayed connected—as former leaders, friends and colleagues—and these relationships, which started in a single summer, have grown in countless ways. The Overland community is powerful network full of not only strong friendships, but also connections to job opportunities worldwide. Overland leaders go on to attend graduate programs, teach abroad and work in a wide variety of professional fields.

In the end, leading for Overland is far greater than the sum of its parts. There’s exciting adventure, great people, important commitments, endless challenges, a supportive community and a vibrant network—but there’s more, too. There’s the chance to deepen and broaden your leadership skills while discovering just how beautiful and exciting, how full of promise the world is.

We encourage you to apply to join us. Everyone on the Overland year-round staff is eager to read your application and to meet you.  We look forward to hearing from you!

Click HERE to see if Overland is coming to a college campus near you!

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Minimum Requirements & Expectations:

Overland looks for college first years, sophomores, juniors, seniors and graduates with a strong desire to work with young people, extensive leadership experience, excellent judgment, superb problem-solving skills, success working in team settings and leading with others, patience, humor and the determination and stamina to succeed in a challenging environment. The Overland community is supportive, wholesome and inclusive, and they seek individuals from a wide range of backgrounds, interests and perspectives. Key qualifications below:

  • Passion for working with kids in an outdoor environment

  • A valid driver’s license

  • The ability to lift and carry 40 lbs. or more of gear or equipment

  • The ability to pass a swimming test and lifeguard certification course (offered at training)

  • CPR/AED and Wilderness First Aid certifications valid through August 9, 2020 (not necessary at time of application)

  • A clear driving record, a positive local police check, CORI, SORI and three written references

  • A recent physical indicating excellent physical and mental health

  • Some (but not all!) trips require specialized hiking and camping skills, bicycling experience or foreign language skills


Application Process

The application process consists of a written application and resume, three references and an interview. Our leader hiring team aims to find a good fit between an applicant and a trip, as well as between co-leaders. We invite you to apply and look forward to getting to know you.

2020 Application Deadlines:

Overland has three application deadlines over the course of the year, and applications will be assessed on a rolling basis. Overland continues to accept applications beyond March 9th. However, positions are typically limited in late spring.

  • November 11, 2019

  • January 6, 2020

  • March 9, 2020

Dates of Employment:

Our leaders arrive in mid-June for our 10-day Leader Training. At the end of the summer, the entire staff returns to Williamstown for Leader Closing. Leaders depart on Sunday, August 9.

Leader Compensation:

Salaries for first year leaders range from $2,000 to $2,500 based on previous experience and the leader’s role and responsibilities at Overland. In addition, Overland pays:

  • 50% of the leader’s travel expenses to-and-from Williamstown (up to $250)—Overland also organizes shuttles from Boston and Albany airports, or carpools from other locations (when possible)

  • WFA expenses (up to $200).

  • CPR expenses (up to $50).

All trip expenses while leading are provided: all flights, accommodations, meals, and activities (for example, rafting, kayaking, ice climbing, etc.). In the field between trips, leaders receive two nights of hotel accommodations and all meals.

Overland also provides access to pro deals as well as discounts on Trek and Surly bikes. All Overland leaders receive branded clothing and gear (Nike Dri-Fit T-shirts, Hydro Flasks, etc.).

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