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 (firstname.lastname@example.org). We look forward to hearing from you.
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.
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.
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.
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.
Growing up on an island in the Pacific Northwest, I loved adventuring and exploring the outdoors. I spent many summers hiking on Mount Rainier, exploring the North Cascades, biking around the island, and paddle boarding at my friend’s house.
Originally from Bainbridge Island, Washington, I am a rising junior at Bowdoin College studying mathematics and education. I am an officer on the rowing team and spend lots of time out on the water training, competing and hanging out with teammates. Last fall, I led an orientation trip for incoming freshman hiking in the mountains, and I’ve fallen in love with all Maine has to offer. Additionally, I volunteer at the preschool on campus and work at the coffee shop. After studying abroad in Prague next fall, I will be doing research with an education professor about play-based learning in STEM fields.
This summer, I couldn’t be more excited to be outdoors and spending time with Overland students and getting to know each of them. From the joy of completing a challenge to the small, daily moments that will make us laugh, I’m grateful for all this opportunity has to offer.
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.
Juan Vasquez Ninco
Born and raised in Colombia, I was fortunate enough to attend high school in Wisconsin, and when I graduated, I joined the Marines. It has been a wonderful seven years since. I’m grateful to say I’ve just completed my second year at Williams College, and I’m thrilled and honored to be a returning leader for Overland this summer.
There are several leadership traits that I aim to share with Overland students. Among those traits, I find that leading by example, being humble, and genuinely caring for your fellow teammates enough to put their needs above your wants are of great importance. As I look ahead to a summer of exploration and growth on Pyrenees Expedition, I’m grateful for the community at Overland, and I look forward to stepping back into a leadership role. Most importantly, I believe leadership is being able to love and care for all of the team members. I’ve learned that leadership does not only rest on the “leader.” In a team, we all can and should lead. This summer, I’ll strive to empower and encourage ownership in each and every team member over our summer adventure!