Each summer, we offer six weeks of hiking, language, and service trips across the country and around the world. We hire students and recent graduates to lead these outdoors programs. Whether you’re summiting peaks in the Rockies, kayaking through fjords in Norway, helping students learn to read in New England, or restoring trails in Alaska, your mission is to catalyze in students an understanding of the world beyond themselves, beyond their own needs and wants, and inspire them to come together as a team and see how beautiful and exciting, how full of promise the world is.
What is an Overland summer like?
There are three parts to an Overland summer: training, leading and closing. The Overland summer begins in early June with Leader Training in Williamstown, Massachusetts. The entire staff camps and shares all meals through two weeks 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.
Overland leaders co-lead a trip or a series of trips with one or two other leaders. For six weeks, 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 a positive role model 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 the staff, debrief their leading experience, and follow up with their students via written communications.
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. Here is the link to our 2026 Application!
Application Deadlines
Overland has three application deadlines over the course of the year:
Sunday, November 30th
Sunday, February 1st
Sunday, March 29th
Minimum Requirements & Expectations
Passion for working with kids in an outdoor environment
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, bicycling experience, or foreign language skills
Dates of Employment
Our leaders arrive in Williamstown, Massachusetts on June 14th for Leader Training. At the end of the summer, the entire staff returns to Williamstown for Leader Closing. Leaders depart August 10th.
Leader Compensation
Salaries for first year leaders range from $2,750 to $3,250 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 & CPR 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.
