The most impactful summer of your life


Apply to Lead

Imagine a summer of adventure,commitment,
and community.

34 itineraries, 8 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 those around you. This commitment drives and informs your leadership every moment of every day.


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Far more than counselors, Overland’s leaders are role models of the highest caliber. Our leaders focus on creating supportive and wholesome environments where each student can flourish.


Leading for Overland is far greater than the sum of its parts. It’s the chance to deepen and broaden your leadership skills while discovering – and showing your students – just how beautiful and exciting, how full of promise the world is.


Leaders stay connected in a vibrant community that stretches far beyond the summer. For 40 years, leaders have stayed connected—as friends, colleagues, a professional network—and these relationships, which started in a single summer, have grown in countless ways.

info sessions

To learn more about Overland, check back here in October and RSVP for an Info Session

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how to apply

The application process consists of a written application and
resume, three references, and two rounds of interviews. 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.

To learn or ask questions, email our Leader hiring team:
[email protected]

Minimum Requirements & Expectations

  • Passion for working with kids in an outdoor environment
  • Be at least 18 years of age and have completed at least 1 semester of college/university
  • A valid driver’s license
    • While the majority of our trips require leaders to have had a valid driver’s license for at least 2 years, a select few trips do not have this requirement
  • 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, 2024 (not necessary at time of applying, and Overland can help reimburse leaders for these certifications)
  • A clean 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 or foreign language skills

Dates of Employment

Our leaders arrive in mid-June for our 14-day Leader Training. At the end of the summer, the entire staff returns to Williamstown for Leader Closing. Leaders depart in early August.

Leader Compensation

Salaries for first year leaders range from $2,500 to $3,000 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)
  • Wilderness First Aid and CPR/AED certification expenses (up to $350)
  • And, of course, 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 and discounts on outdoor gear. And, all Overland leaders receive branded clothing and gear (Nike Dri-Fit T-shirts, Klean Kanteens, etc.).

To learn or ask questions, email our Leader Hiring team at [email protected].

Summer after summer, Overland students are the most thoughtful, strong, and fun people I know.

Seeing my groups bond and overcome challenges gives me so much hope; it’s the reason I lead for Overland.”

Lilly Bianchi

St. Lawrence University

One lesson I keep reflecting on is how kids are so powerful.

The students we worked with were 11-13 years old. They are at this amazing inflection point; they can do anything with their lives. It was a beautiful thing to facilitate that promise they had within them.”

Charlie Cox

University of Virginia

your questions,

With 40 years of experience, we’ve learned what works and what doesn’t when crafting a great outdoor summer experience. Our team is just a phone call or email away.

Have more questions for the Overland team?
Contact Us or call: (413) 458-9672

When does the leader application open?

Our application for the summer of 2025 will open in early October, 2024.

What do you look for in prospective leaders?

We look for college students 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 2023, Overland gave approximately $340,000 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 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 Field Staff. Field 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. Field 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 Field 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.

What trips do you offer?

We offer trips in over 50 locations across the U.S. and abroad, including Switzerland, France, Spain, Iceland, Norway, and Tanzania. Our trips include hiking, service, and language; 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 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 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 are meals like at Overland?

Good food (and plenty of it!), excellent nutrition, and fun are the goals of Overland’s meals. Each group buys, prepares, and eats all of its meals together. Our students, with their leaders’ supervision, prepare all meals. At Overland, meals are a group experience, an important way to foster connection with and consideration for other group members.

Allergies & Intolerances

We recognize there are many people with food allergies or intolerances. We welcome these people’s interest in joining us, and we ask prospective Overland leaders with an allergy/intolerance to please consider the following important information.

Most meals at Overland are prepared in basic kitchens (or outdoors), and groceries are typically purchased from small stores with limited choices. As a result, meals are prepared and served in what may be allergen-contaminated environments, and on some trips allergen-free/gluten-free foods are not readily available. If a prospective leader has an allergy/intolerance that constitutes a disability, we will engage in an interactive process with the prospective leader to determine whether there is a reasonable accommodation that would allow the prospective leader to perform the essential functions of the positions.

In all things, our top priority is to help maintain our students’ and leaders’ well-being; to this end, all Overland leaders are trained to recognize and respond to allergic reactions, including administering antihistamines and epinephrine (both are carried in every trip’s first aid kit). Leaders also carry cell phones, and in some cases, satellite phones, so that should the need arise, emergency personnel can be contacted and their services requested. It is important for all prospective leaders to understand that many groups travel in remote areas where emergency services may not be easily or readily accessible.


Every summer there are many vegetarians who join our groups and who enjoy meat-free meals. We are happy to welcome these students and leaders as long as they understand they will share in the group’s meals but will simply have the meat portion withheld. For example: sandwiches at lunch with hummus, lettuce, tomato, and cheese (while the rest of the group has sandwiches with sliced turkey or ham); pasta at dinner with a tomato sauce (while the rest of the group has pasta with a meat sauce).

Vegan & Specialized Diets

We sometimes have requests from student and leader applicants with specialized diets—vegans, for example—to provide separate, specialized meals. As much as we’d like to be able to accommodate these applicants, the limitations of our kitchens, the size of available grocery stores, and the importance of group meals make it impractical to provide separate, specialized meals.

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 lifeguarding 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. Overland provides workers’ compensation and general liability protection but does not provide health insurance for seasonal staff.

Is Overland an equal opportunity employer?

Yes. 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.

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Info Sessions

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