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.

Eight Summers with Overland

Independence & Self-Reliance

An Overland group ice climbs in Alaska

At Overland, we have always known that it is the people who make this community so special. In recent days, we have been reminded of that more than ever. In speaking with Lucy, a longtime Overland student, we heard again and again the value of a supportive group of people in making an incredible summer experience. Lucy was a student on Berkshire Adventure, Mountains & Sea Adventure, Yellowstone Adventure, Maine Coast Leadership, Alaska Explorer, High Sierra Expedition, Alaska Challenge, and the American Challenge. Her reflections below remind us of the joy we find in a group, and the strength in our Overland community.

Overland students are able to articulate the true value of an Overland summer more than anyone else in the community. A multi-year student, Lucy Flanagan has spent eight summers—eight!—on Overland trips. She’s currently a high school senior, and her love of the mountains has led her to commit to Colorado College for the fall. We asked Lucy what it’s like to be a returning student. She shines light on what makes Overland unique and what keeps her coming back, naming ritual, community, and challenge as a few of the elements that make Overland trips so special.

1. What is the through-line between all of your Overland summers? In other words, what keeps you coming back every summer?

It’s really hard to choose just one thing, but every year I just want another Overland experience. I always want to explore a new area of the natural world, especially with a tight-knit group, Overland-style. After eight summers with Overland I’ve never ever been disappointed with my group or my leaders, so by this point I positively know I’ll be in for something great. My Overland summers are a chance for me to create new and everlasting relationships with my peers and leaders alike, without any preconceived judgements based on social media, rumors etc.—the stuff that goes on in other teenage settings. It’s kind of a fresh start. The Overland traditions that I hold so close to my heart—like dessert circle, chores crews, or even that awkward initial airport meeting—keep me coming back every summer. 

One of Lucy’s first Overland groups in Yellowstone National Park
2. Part of what can make an Overland trip so powerful is overcoming difficulty. Tell a story of a challenge you overcame with your group on an Overland trip. How did this experience translate back to your life at home? 

One of my most difficult moments at Overland came on my Alaska Challenge group’s four-day trek of Kesugi Ridge. After a picture-perfect view of Denali, we were getting tired, and by the end of the day the winds had started kicking up a lot. Huge storm clouds were forming ahead. We got to camp, and it was so windy that we couldn’t even hear each other talking. Setting up camp in that wind was nearly impossible. Cooking dinner was a whole ordeal in itself, the wind putting out most of our flames on our stoves. I was feeling a little nervous and uncomfortable. We were huddled up eating dinner on our bear cans when the rain started coming down, and it started coming down hard. We scurried to get everything under our tents, and called it early that night to get warm in our sleeping bags. That night, me and the three other girls were so there for each other. It was scary with the wind pounding on the tent walls and the rain coming down so hard, but we were constantly reassuring each other that it would be okay. The rain didn’t stop the next morning, and it rained all day long. We were completely soaked, but we played contact, told riddles, made up songs, and made the rain funny. After three days straight of rain, all my clothes were soaked, so two guys on the trip lent me their only pair of clean socks. When I felt really sick and cold one of the nights, another friend brought me granola bars. We needed each other so badly during those times, and the next day the rain stopped. I don’t think I’d ever emotionally make it through those rainy days without the support of my group. At home, this made me rethink the way I approached uncomfortable conditions. It changed my perception of what constitutes a “miserable situation,” but also taught me the importance of group cohesion and individual attitude to group success. If you’re in a tough situation, a bad attitude really won’t fix things—so I try to never complain when I’m in unfavorable, but uncontrollable, circumstances. 

Overland students in Alaska
Lucy and her group learn how to ice climb in Alaska
3. Tell a story of a beautiful and joyful moment at Overland. How did that moment impact you?

On the American Challenge bike trip, we rode 110 miles in one day, from the western end of the Oklahoma panhandle to Raton, New Mexico. We fell short the day earlier and hadn’t gotten much sleep. I was stoked to be getting out of Oklahoma, and after roughly 20 miles of battling vicious headwinds we hit the New Mexico sign. But to my surprise, the headwinds did not stop as soon as we left Oklahoma—they actually persisted far into New Mexico. The scenery was still drab, as we rode through miles of cornfields and windmills. But slowly, I saw rolling hills form and those hills started turning into mountains. It was still windy, and we even got a surprise mountain storm halfway through the day and had to station at a restaurant until it passed. It didn’t seem possible to make it to Raton which was another 30 miles out, but eventually the rain stopped and we kept pushing. It was so much climbing—another 10 miles or so—when our leaders told us we had a 20 mile descent. The sun was setting, and the rays beautifully punctured the clouds in front of us. The mountains opened up as we descended into the Rockies. I heard shrieks of joy all the way down the descent from everybody in my group. The scenery had gone from Oklahoma plains to the Rocky Mountains in one day, right before my eyes. The temperature was perfect. The scenery was so majestic; I don’t know if I’ll ever match such pure joy of seeing that view with my tight-knit group. Each and every one of us wore indescribable smiles when we met at the bottom of the descent. This really taught me to appreciate the natural world, more than I’d ever thought. I appreciate those incredible views so much more—especially given that I live in the Midwest. Moreover, it made me appreciate the struggle—because when you’re in difficult circumstances, it makes it so much better when you’re out of them. I don’t think I would have been as happy during the descent if I hadn’t just pushed through three days in the Oklahoma panhandle. 

Lucy celebrates with her group in the Pacific Ocean
4. How does it feel to come back for multiple summers? How do you keep it fresh, after so many Overland trips?

I have never ever gotten bored with an Overland trip. Every day is a new adventure, and every group is so unique from one another. Just because I’ve gone back each summer doesn’t make me feel like an Overland “pro” per say. Every summer is new, and I at first feel just as clueless as my first year, but this newness makes my experience more exciting. Every year I’m ready to get away from my phone, and to be my most raw and open self with people I’ve never met before. There are new niches to fill in the group every year, and I’m always a different person than I was the year before, so no experience has ever been like the last. 

5. What have you learned from Overland that you will carry into the future? 

Overland taught me, most importantly, the power of group cohesion to individual and group success. I am very community oriented, and I know this because of my summers spent making new connections with my Overland groups. I have a deep appreciation for the outdoors and its wonders, and the types of relationships that nature can foster. My Overland summers were all so fun, but challenging in their own ways, and now I know that to successfully make it through any challenge—whether it be climbing Ship Lake Pass in Alaska, or something as minuscule as walking to school in the rain—I need a good attitude.


Filed Under: Teen Summer Adventures / High School Adventure Programs / Student Perspectives

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