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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.

Imagine a summer of adventure, commitment and community.

49 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.

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 30 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. Apply today—we look forward to hearing from you!

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.

Application Deadlines

Overland has three application deadlines over the course of the year, and applications will be assessed on a rolling basis. If you plan to study abroad in the spring, please apply by the fall deadline.

Preliminary Interview

A preliminary interview gives us a chance to get to know you and learn more about your experiences before you apply. It’s also a great chance for you to better get to know Overland and its culture. Our team of recruiters travels to college campuses and major cities around the country throughout the year. To see if there will be a recruiter near you, please refer to our Campus Visits Schedule. For more information, email Conor O’Brian at conor@overlandsummers.com.

Minimum Requirements & Expectations

  • 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 5, 2019 (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
  • Many trips require specialized hiking and camping skills, bicycling experience or foreign language skills

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 Monday, August 5.

Leader Compensation

  • $2000 salary for first-year leaders
  • All trip expenses, including transportation from Williamstown to the trip start and back at trip end
  • Access to prodeals through Experticity and outdoor Prolink as well as discounts on Trek and Surly bikes
  • Partial reimbursements for CPR, Wilderness First Aid and travel expenses to and from Williamstown


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"I've enjoyed every summer I've spent with Overland because it is an environment of caring. There is a tremendous investment in each leader and each student, and leadership presents leaders with the challenge of being our best selves. My experience has always been one of incredible challenge and growth."

Isaac Merson, Bowdoin College ‘17

Mountains & Sea Adventure, North Country Adventure, Yellowstone Teton Explorer

Read more about Isaac

“I truly love leading for Overland. I love seeing kids grow tremendously over the course of just a few weeks. I love meeting and getting to know these intelligent and mature kids. Watching the group work together to meet demanding challenges and achieve physical goals is incredible. I love watching friendships blossom in the least likely of places. I love it all. It simply does not get more rewarding.”

Sara Becker, University of Michigan ‘16

North Country Adventure, Language & Service Costa Rica, Field Studies Patagonia, Field Studies Tanzania, Pyrenees Expedition

Read more about Sara

“Leading for Overland was one of the most challenging and most rewarding things that I have ever done. Despite knowing that I had a challenging summer ahead of me, I left for Costa Rica feeling extremely prepared and capable of co-leading our trip; I think that this is a testament to the thoroughness and effectiveness of training. I felt nothing but welcomed and supported by the office. Overland is a great company to work for.”

Jordyn Adeboye, Carleton College ‘15

Language & Service Costa Rica, Language & Hiking Spain

Read more about Jordyn

“Thank you for cultivating an environment where bottom-up input is recognized, respected and used to catalyze change. I am absolutely blown away by the growth I have seen in Overland's financial aid since I started leading in 2015.”

Arden Simone, Davidson College ‘17

Berkshire Adventure, Field Studies Tanzania

Read more about Arden

“Professionalism, communication and kindness are three words that describe the true Overland experience.”

Will Haslett, Colorado College ‘20

Berkshire Adventure, Rocky Mountain Explorer

Read more about Will

“I enjoyed working with the office and all of the full-timers. When I reached out to them with concerns, they were extremely qualified and helpful. This summer, I grew a lot as a person and especially as a leader.”

Camila Trejo, University of Southern California ‘20

Berkshire Adventure, New England Adventure, Cape Cod & the Islands

Read more about Camila
  • What do you look for in prospective leaders?

    We look 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 we seek individuals from a wide range of backgrounds, interests and perspectives.

  • Who are Overland's students?

    Our students are 9 to 18 years old and come from across the country and around the world. Every summer about half of our students are back for a second, third, fourth or fifth summer. We are committed to broadening access to all of our trips through our scholarship and financial aid programs. In 2018, Overland gave almost $240,000 in financial aid.

  • When can I expect to hear from Overland?

    We notify applicants of their status within 2-3 weeks of applying. Finalists are invited to interview. After that, we extend offers for specific trips to our top candidates. Also, we ask a select group of strong candidates to be in our reserve pool for positions that may become available in the spring. Approximately 20 leaders are hired from the reserve pool each year.

  • How many applications do you receive?

    We typically receive more than 1,000 applications and hire about 120 new leaders; roughly half of our staff each year is made up of returning leaders.

  • Where do college first-years lead?

    We hire students finishing their first year of college to join our New England Support Staff. Support Staff is a dynamic role with a varying daily schedule that could include assisting with trips and in the office, organizing gear, shuttling groups in 15-passenger vans, meeting groups in the field and filling in wherever necessary. Support Staff members live together in a house in Williamstown during the summer, form a tight-knit community through shared tasks and meals, and have no living expenses during the summer. Members of Support Staff typically lead one or more weeks of a New England-based introductory trip.

  • Where do college sophomores, juniors, seniors and graduates lead?

    First-year leaders for Overland who are sophomores or older lead trips across the U.S. and abroad.

  • How are trip placement decisions made?

    We consider an applicant’s written application, previous leadership experience, references and interviews. We look for a match between the new leader, their prospective co-leader and a trip. Leaders of language trips must be fluent in French or Spanish and must have studied abroad.

  • What is an Overland summer like?

    There are three parts to an Overland summer: Leader Training, leading and Leader Closing.


    The Overland summer begins in mid-June with Leader Training in Williamstown, Massachusetts. The entire staff camps and shares all meals during 10 days of seminars, hands-on workshops and a multi-day hiking or biking trip. Leader Training is a time to sharpen leadership skills, master the details of trip logistics and build effective working relationships with co-leaders and the full-time staff.


    Over the course of six weeks, Overland leaders co-lead a trip or a series of trips with one or two other leaders. Leaders are responsible for maintaining the health and well-being of their students, managing day-to-day logistics, transporting students in a 15-passenger van (on some trips towing a utility trailer), working within a budget, planning and organizing meals, completing required paperwork, communicating with the Overland office and photographing the experience. Leaders manage risks in the field and serve as positive role models to students, working to bring every member of the group together as a team.


    The Overland summer ends the first week of August with Leader Closing in Williamstown, during which leaders reconnect with the rest of our staff, debrief their leading experience and follow up with their students via written communications.

  • What trips do you offer?

    We offer trips in over 50 locations across the U.S. and abroad, including Canada, Europe, Central and South America, Iceland, Norway and Tanzania. Our trips include hiking, biking, service, language and writing; the trips range from one to six weeks in length, and they vary in difficulty from introductory experiences for our younger students to challenge trips for our older students.

  • What reimbursements do you offer for certifications and travel?

    We reimburse for CPR/AED (up to $50) and Wilderness First Aid (up to $200). While you do not need any certifications to apply, if hired you will need to arrive at leader training with CPR/AED and Wilderness First Aid (we offer a lifesaving course during our leader training). Overland partially reimburses travel to and from Williamstown at the start and end of the summer. Please Note: Leaders are responsible for loss or damage to their personal gear and bicycles. Overland provides workers’ compensation and general liability protection but does not provide health insurance for seasonal staff.

  • Overland Is An Equal Opportunity Employer

    Overland Summer Camps, Inc., prohibits discrimination against and harassment of any employee or any applicant for employment, or any camper or any applicant to join one of our camps, because of race, color, national or ethnic origin, age, marital status, familial status, genetics, ancestry, religion, disability, sex, sexual orientation, gender identity and expression, veteran or military status, military service or any other characteristic protected under applicable federal or state law. All personnel responsible for hiring and promoting employees, for admitting and enrolling campers, for leading and supporting campers, and for developing and implementing camp trips or activities are charged to support this effort and to respond promptly and appropriately to any concerns brought to their attention. Individuals who feel they have been treated in a way that violates this policy and/or federal, state or local employment laws are encouraged to notify one of Overland’s directors. Overland will not take any retaliatory action in response to an individual’s complaints.