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
Available
This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.
Limited
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.
Waitlist
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.
Questions?
Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.
Our Leaders
Far more than simply counselors or guides, Overland’s leaders are terrific role models for our students. Capable and caring, our leaders focus on creating supportive, wholesome environments where every student can flourish and grow.



1000 applicants
We recruit our leaders from America’s finest colleges and universities, meeting with campus leaders across the country—an effort that generates hundreds of applications every year.
300 minutes
We typically spend over five hours evaluating our finalists: there are two readings of the application, a thorough review of three references, a three-part background check, and an interview.
200 leaders
In 2022, over 200 individuals led for Overland. A mix of first year and returning leaders, our leaders include top students, athletes, and campus leaders—ideal role models for our students.
50 colleges
We recruit our staff from some of the country’s top schools and rely on our network of leaders at these schools to produce a deep pool of qualified applicants.
10 days
From extensive pre-summer preparations (first aid certifications, readings, and videos) to a demanding training session in Williamstown in June, our leaders invest ten days (minimum—for many leaders it's more) preparing for the summer.
1 goal
Our talented leaders have one goal: the success of each of their students. This, perhaps more than anything else, has made the difference for us as an organization and for the thousands of students who have joined us.
Meet Some of Our Leaders
With a wide range of backgrounds, hometowns, schools, and colleges, all of our leaders have one thing in common: a rock-solid commitment to our students. Our leaders focus every day on their students’ health and well-being as they seek to nurture and inspire everyone they lead.

Chelsea Colby
Middlebury College
I teach second grade in Cornwall, Vermont, where I am the school’s beekeeper and love taking my students out snowshoeing and Nordic skiing every winter.
Originally from Meredith, New Hampshire, I graduated from Middlebury College in the winter of 2018 as an environmental policy major and education studies minor. While on campus, I was a Vermont Campus Compact/Vermont Higher Education Council Engaged Student Award Recipient, and I received the Bonnie McCardell Student Leadership Award for outreach in youth and family services. During college, I fell in love with the community in Addison County, Vermont, so I began my teaching career at a local elementary school. I have worked with multiple elementary ages, but currently teach a close-knit group of 9 spunky and sweet 2nd graders. During winter weekends, I teach alpine skiing to students of all ages at the Middlebury College Snow Bowl. When I’m not teaching, you’ll find me hiking a mountain.
In 2022, I led Rocky Mountain Expedition and I am thrilled to be returning to the Overland team this summer! As a leader, I love to experience the intense and wonderful power of immersive outdoor experiences and the ways that they invite us to grow as individuals and bring us together in community.

Gonzalo Escajadillo
Tufts University
Throughout high school, I used my language skills to teach ESL in three languages, and live translated civic prep classes. These experiences helped shape the way I intentionally communicate with those around me.
Growing up internationally, I graduated high school in Darien, Connecticut in the spring of 2021. The following fall, I started attending Tufts University, where I am now a sophomore majoring in Chemical Engineering. As a member of the Men’s Crew Team, I spend a lot of my time on campus working with my teammates both on and off the water. I am also a volunteer radio show host for Tufts’ freeform radio station, where I’m on air for an hour a week playing music for the community. Outside of academics and rowing, I spend my time exploring new music, playing frisbee, and reading books.
I’m excited to return to Overland’s staff this summer. As a four-time Overland alum — including summers on Alpine Challenge and Kilimanjaro Expedition — and a leader last summer — on Berkshire Adventure and Alaska Explorer — I know firsthand that Overland is a great place to grow and learn from the outdoors and peers, and I’m excited to be a part of the process this once again.

Olivia Ng
Davidson College
Riding through the Canadian Rockies, hiking over craters in Korea, and watching penguins skip through the icy waters of Antarctica have continued to inspire me to share my love of active traveling with others!
Originally from Raleigh, North Carolina, I am a 2021 graduate of Davidson College, where I majored in environmental humanities and minored in Hispanic studies. At Davidson, I was a trip leader for Davidson Outdoors––our outdoor leadership and adventure program––where I led backpacking and stand-up paddle boarding trips for other students. Throughout my time in college, I became incredibly passionate about sustainable living and global environmental issues. I also love languages and traveling! Throughout my time at Davidson, I studied abroad in Cadiz, Spain, and in Ushuaia, Argentina- located at the southernmost tip of Latin America! There, I studied Spanish, climate change, ecology, marine biology, and human relations with the environment.
I led in 2019 and 2021, and my favorite part of each summer was spending time outdoors with my students and watching their independence and confidence grow as a group! I’ll return to Overland this summer to lead Language and Hiking Spain, and I can’t wait.

Caroline Green
Barnard College
After going on an Overland trip when I was eleven, I fell in love with nature and exploring it with others, and I returned for another five summers of outdoor adventure.
Originally from Pittsburgh, Pennsylvania, I am a sophomore at Barnard College. I have loved getting involved on campus – I play on Columbia’s ultimate frisbee team and joined a Hillel leadership fellowship, meeting weekly with other first-years to discuss and improve our leadership on campus. I earned fall semester Dean’s List honors and have enjoyed taking classes in many disciplines before declaring a major. Aside from academics, I love exploring NYC and finding natural beauty in the urban landscape, which I often find while running in nearby parks. I am passionate about photography and can frequently be found holding a camera, whether I’m out exploring or in any daily moment.
When I look back, Overland trips have been incredibly formative times in my life; they have changed the way I see the world and my place within it, as well as given me fond memories and lasting friendships. I know how special Overland experiences can be, and I’m so excited to lead in California this summer, helping students explore Overland’s promise.

Tristan Alston
Swarthmore College
In the fall of 2018, I spent a week canoeing along the Delaware Water Gap with a group of my freshman year classmates. It was my first—and only—multi-day canoe trip, and my first experience island camping!
Originally from Housatonic, Massachusetts, I graduated from Swarthmore College in 2022 with an honors major in Peace & Conflict Studies and minors in both Black Studies and Environmental Studies. While at Swarthmore, I was a member of the varsity track and field team, a peer mentor in the writing center, as well as a student photographer for the communications office. I also engaged in independent research as a Mellon Mays Undergraduate Fellow, and, as a Lang Opportunity Scholar, I developed the Berkshire Equity Research Collaborative (BERC)—a youth-centered participatory action research project that aims to promote diversity and inclusion in local schools. In my free time, I enjoy photography, playing guitar, snowboarding, and backpacking.
As someone who is deeply passionate about enjoying, connecting to, and conserving the natural environment, I’m thrilled to lead for Overland again this summer, and to encourage Overland students to build meaningful relationships with each other and the great outdoors. Last summer on Northwest Expedition was a total blast — I can’t wait to do it all again!