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 hundreds of campus leaders across the country—an effort that generated hundreds of applications in 2021.
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.
Caitlin Beakes
University of North Carolina at Chapel Hill
This past year I worked at the Breckenridge Outdoor Education Center as an adaptive ski instructor, teaching people with cognitive and physical disabilities how to ski.
Originally from Chevy Chase, Maryland, I graduated from the University of North Carolina at Chapel Hill in 2018. I double majored in Kinesiology and History and minored in Spanish. I was the Captain of the Women’s Varsity Rowing team and a four-year member of the Carolina Leadership Academy. The first year following my graduation I worked through WWOOF (World Wide Opportunities on Organic Farms) at farms in California, Hawaii and Italy. Before I started at the Breckenridge Outdoor Education Center I worked for several months at a winery in Portland, Oregon, and then made my way out to the Rockies from there! My favorite activities include running, watching UNC basketball, and petting dogs.
I led Maine Coast Explorer in 2018, Norway Explorer in 2019, and the American Challenge in 2021 and 2022. In all of these trips, we enjoyed amazing moments and faced down imposing obstacles. I truly appreciate the supportive, challenge-hungry environment that Overland creates for its groups!
Gia Monachino
Columbia University
Growing up in San Francisco, I was perfectly situated to take advantage of California’s varied landscapes and environments, from the beaches of the Central Coast to Yosemite Valley.
Being familiar with city life brought me to attend Columbia University in the City of New York, but my original love and appreciation for nature led me to study and graduate with a degree in environmental sciences, along with psychology. At Columbia, I was on the track and field team. My professional life has always revolved around working with children and youth, including working at summer camps, coaching basketball, volunteering at a Harlem elementary school, and babysitting for families around San Francisco and New York City. When I am not outdoors, I love crocheting, baking, and studying the French and Italian languages. I have been fortunate enough to spend most of my life traveling as my family is from the United Kingdom and Italy, and I am a British citizen myself. Because of my love for travel and experiencing new cultures, I plan on living and working in Paris as an au pair this upcoming school year.
I look back on the camps and programs I attended as a child as some of the most important and influential experiences of my life, and I recognize they were made even more special by my counselors and leaders. Leading Yellowstone Teton Explorer in 2021 and Language and Hiking France in 2022 gave me the opportunity to inspire the next generation of leaders and create incredible summertime memories for youth.
Chris Johnson-Harwitz
Harvard University
After backpacking for the first time as a freshman in college, I fell in love with the outdoors and became a hiker, rock climber, trail runner, Wilderness First Responder, and more!
Right in my hometown of Cambridge, Massachusetts, I am a rising senior at Harvard University studying Molecular and Cellular Biology and Psychology. On campus, I’ve spent time doing research on cancer immunotherapy and modeling rare liver disease, as well as spending the past year working as a mental health specialist at McLean Hospital as I look forward to applying to medical school. Outside of class, I’ve spent much of my time leading and coordinating outdoor trips through Harvard’s First-Year Outdoor Program, running outdoor pre-orientation trips for first-year students. When I’m not outdoors, I can be found cooking, writing music, or dancing.
Leading Rocky Mountain Expedition in 2021 was an incredible opportunity for me to share my excitement and passion for the outdoors with a group of younger people. There’s a certain kind of joy that only spending time in the outdoors can bring me, and it was incredible to see that joy reflected in young people’s faces.
Olivia Ng
Davidson College
A single glance at the icy blue waters and a breath of cool, crisp air in Banff, Canada, fueled my love for the outdoors, the environment and sustainability.
Originally from Raleigh, North Carolina, I am a junior and environmental studies major and Hispanic studies minor at Davidson College. I am a trip leader for Davidson Outdoors — our outdoor leadership program — where students lead backpacking, paddling, climbing, caving and biking trips for their peers. Passionate about sustainable living and global environmental issues, I started living a zero-waste lifestyle in August of 2018. Also, I started to help operate the industrial composter and share my passion for the environment through communications and social media for Davidson’s Office of Sustainability. In the summer of 2018, I studied abroad in Cadiz, Spain, where I immersed myself in the Spanish language and culture, traveled to more than eight cities and spent a weekend in Morocco — loved every minute of it. This fall, I studied abroad and conducted research in the southernmost city in the world in the Patagonia region of Argentina and will have the opportunity to go to Antarctica for 10 days. In my free time, I love taking my bike for a spin around Davidson, trying new recipes and spending time outdoors with my friends.
In 2019, I led Mountain and Sea Adventure and in 2021, I led Pacific Coast. I am eager to share my love for the outdoors and environment with students, foster new friendships, watch their confidence grow and make this summer the most memorable of their lives.
Wilson Kaplan
Colorado College
The summer before my junior year of high school, I spent a month backpacking in the Wind River Wilderness. The trip sparked my interest in camping and hiking and showed me the importance of an outdoor trip.
Originally from Great Barrington, Massachusetts, I graduated from Colorado College in 2020 with a degree in organismal biology and ecology. Living in Colorado gave me great opportunities to ski and hike—two of my favorite activities. I have backpacked in several areas of the Colorado Rockies including the Collegiate Range and the Gore Range. I also spent a summer building and maintaining trail systems in the Sangre de Cristo Mountains. After graduating, I have worked removing invasive species and restoring native habitat in western Massachusetts.
In 2018, I led Mountains & Sea Adventure, in 2019, I led Sierra Adventure, in 2021, I led Northwest Expedition, and in 2022, I led Alpine Challenge. I love leading for Overland because there’s so much inspiration and imagination in the leaders, campers, and places we go.