We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

Join Our Team

Williamstown, Massachusetts

We welcome your application to join our year-round team.

The Overland year-round team is a group of professionals dedicated to advancing our mission to inspire our students to see how beautiful and exciting, how full of promise the world is. We are recent college grads; we are part-time employees and full-time parents; we are volunteers and coaches; we are hikers and bikers; we are East Coasters; we are West Coasters; we are inclusive and welcoming.

Based in Williamstown, Massachusetts, we are members of a small-town community in a beautiful corner of New England. The seasonality of both Williamstown and Overland imbues each phase of the year with varied tasks, projects, and responsibilities. Beginning in September, our work builds towards peak admissions season in the winter, then transitions to summer preparation in the months between January and June. Our six-week summer season is a time of energy and action; it’s the goal we’ve been striving towards all year. For over 35 years, Overland has created superlative trips and lasting experiences for our students—as a team, that’s what drives us forward.

Annual Opportunities

Admissions & Financial Aid. Responsibilities include generating over 2,500 applications for each summer’s trips, traveling across the country to make presentations, working with parents over the phone and via email, and overseeing our financial aid program, Open Arms. As with every position at Overland, members of the admissions and financial aid team will have additional responsibilities that will include assisting with leader recruitment and other tasks.

Leader Hiring. Responsibilities include recruiting, evaluating, and hiring summer trip leaders from colleges and universities across the country. The leader hiring staff works with our current and former leaders to fill approximately 100 spots for each summer’s staff of trip leaders and then generates over 1,000 applications each year for the remaining approximately 100 spots for new leaders. As with every position at Overland, leader hiring staff will have additional responsibilities that will include assisting with student recruitment and can include other tasks (e.g., trip planning and/or managing equipment).

Trip Planning. Responsibilities include managing a group of trips throughout the year, starting with a September review of the previous summer’s experience and progressing through revisions in the fall (which can include travel to scout locations), reservations in the winter, and dialing in the details in the spring. When our summer season begins, trip planners manage their trips from our offices in Williamstown, working with leaders in the field to ensure the smooth operation of their trips. As with every position on the Overland staff, trip planners will have additional responsibilities that will include assisting with leader and student recruitment, managing equipment, and other tasks.

How to Apply

What You Need
Please send a cover letter, resume, and a 300-word statement of interest to founder and director Tom Costley. If you are a recent college graduate, please include a copy of your college transcript.

What We Look For
Applicants for all positions should have excellent organizational skills, attention to detail, and the ability to communicate clearly. We seek team players who are eager to be a part of a dynamic organization where we share responsibilities, support each other, and celebrate our successes.

Overland offers competitive compensation and benefits; a healthy, wholesome work environment; and the chance to be part of a group of people who care about what they do and about each other. Overland 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 members of our team.

Apply Today
Throughout the year, Overland accepts applications to join our team as a full-time or part-time member of the year-round staff or as an intern; apply today, and we will be in touch within one week to follow up.