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.

The Benefit of a New Group Every Summer

Independence & Self-Reliance

A group hiking in the mountains during the summer

Overland is a bit different than traditional summer camp. Instead of returning to the same place with the same people when summer rolls around, Overland students choose and embark on a new adventure. A longtime Overland student may spend every summer in a different state or even country, and it’s likely that they’ll never have the same trip mate twice. We asked some veteran Overland students for their perspective on the Overland experience, how their different trips have built on each other, and what they’ve gained by returning to Overland year after year for a new summer teen adventure experience.

Abbey Wish started with Overland as soon as possible — the summer after fourth grade on the introductory trip Berkshire Adventure. On Berkshire Adventure and then the following year on North Country Adventure, Abbey learned the ropes of Overland and got a taste of hiking, biking, and camping. She discovered a love for biking and decided on Vermont the following year. In Abbey’s words, “It was this trip where I became addicted to Overland.”

A group of students smiling outdoors, including Abbey on her first summer trip
Abbey on Berkshire Adventure

Abbey continued to pursue biking for the next three summers with a clear goal in mind. “After Vermont, I decided I wanted to eventually do the American Challenge [a six-week bike trip which—at the time—started in South Carolina and ends in Southern California]. I knew that the American Challenge was going to be extremely difficult, so for the next two summers I did trips that increased with difficulty… Both the Pacific Coast and Canadian Rockies & Montana let me experience longer days and harder terrain than I had experienced during the Vermont trip. I am extremely happy that I slowly worked my way up to the American Challenge because by the time I did it last summer, I felt prepared and ready. When I got on the bike on the first day of the American Challenge, I knew what to do and had a good idea of what to expect.”

Abby and her American Challenge Group in the ocean holding their bike wheels to celebrate biking across the country
Abbey & her AC Group in the Pacific

Evan Michelman’s first Overland trip was North Country Adventure, and he quickly learned to pitch a tent. Evan honed his camping skills on two more hiking trips with increasing levels of physical difficulty — Yellowstone Teton Explorer and then Alps Explorer (now Alpine Explorer). “[Alps Explorer] was my most challenging trip, but the journey up each mountain was made enjoyable by the people on my trip. The overwhelming views from the top of each mountain in the Alps showed me a part of the world’s beauty.” Last summer, Evan traveled further afield on Field Studies Tanzania. The group experienced safari in the Serengeti, volunteered at an orphanage, and engaged in Tanzanian culture and community—experiences totally new and different from any other Overland trip. But Evan’s hiking trips certainly served him well on the group’s final challenge, a summit bid of Mt. Kilimanjaro.

Evan on North Country Adventure smiling at the summit of a mountain after hiking
Evan & his North Country Adventure Group

For both Abbey and Evan, the common denominator on each Overland trip—no matter the location—is the close relationships they’ve formed with their leaders and trip mates, and the sense of accomplishment after facing a challenge. “By the end of each trip, I had gained 13 new friends, and the last thing I wanted to do was leave them. At Overland, I have learned to drop all preconceived notions before meeting new people and learning about things,” says Evan.

Evan Summits Mt. Kilimanjaro on a summer teen adventure trip
Evan on the Kilimanjaro Summit

For Abbey, challenge and camaraderie at Overland go hand in hand. “Although each of my Overland trips was special in its own way, the accomplishment of biking across America is an experience that I will look back on and treasure for the rest of my life. It was filled with incredible emotional and physical challenges, and overcoming these challenges with the support of my group and leaders was powerful and transformative for me.”

As Abbey and Evan have grown and changed over the years with Overland, so have the trips they’ve chosen, with new adventures to face and tougher challenges to conquer. No matter the itinerary, it is the foundation of the Overland experience that keep Abbey and Evan returning every summer. Abbey says it best: “Overland has taught me the importance of working as a team and supporting each other. It has taught me that difficult challenges can be overcome with hard work and commitment. Also, I have learned that I am stronger than I thought I was, and that when something seems impossible, if you break it down into smaller pieces, it can be done.”

Editor’s Note: Abbey and Evan have gotten to experience a full range of Overland’s summer teen adventure trips, and know that where you go doesn’t matter as much as the people you meet along the way. Read more about a leader’s perspective on the American Challenge here and stories from the trip here. If you’re excited about spending a summer with a wholesome, supportive group, working towards clear challenges in beautiful places, then apply now!

Filed Under: Teen Summer Adventures / Teen Adventure Camp / Student Experiences

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