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.


"As parents, we all want the same thing: to raise children who are kind, resilient, and able to dig deep in those moments when they find themselves in a tough spot. The question is how to do that in a world filled with disparate advice, lots of screens, and many distractions. How tough is too tough? What is too precious or indulgent when it comes to programs? We have found the answer in Overland. Katherine has gone on two Overland trips over the last two summers, and we have seen her grow in confidence as she realizes she has deep reserves of grit and resilience she never tapped before. This latest trip was an incredible physical and mental challenge — the days were long, the heat made the conditions tough, and the hiking was sometimes very difficult, technical, and, frankly, scary. But Katherine and her group persevered, helping each other along the way. The tears shed at the airport as each of the group departed were real, and I know that Katherine has made friends for a lifetime."

Grace Won

San Francisco, California

"My daughter Amelia got home last night from her Service & Hiking Alaska trip, and I wanted to take a moment to extend my sincere thanks for an amazing experience for her. She raved about the trip and [her leaders] Alex and Max. The photos were beautiful, and the trip was really everything my husband and I could have ever asked for for her. I also want to thank you for answering my myriad questions beforehand with patience and kindness and thoroughness. Having never sent a kid on such a trip (even though Amelia is our youngest) and not being a camper, I was out of my comfort level as far as knowledge, and you had such a gentle hand with your responses. It's been a real lesson in getting out of my kid's way and letting her forge her own path. And for that I thank you."

Cindy Daltorio

Maplewood, New Jersey

"Patrick enjoyed both of his previous trips — and so did my older son. These trips give the best balance of freedom, risk-taking, guidance, and fun. I look to Overland to help me develop my boys into healthy, independent, confident men."

Kate Hiebert

Chappaqua, New York

"We can see the impact of Amelia's Berkshire Adventure trip on her confidence, sense of responsibility, and poise in the outdoors. From cooking their own meals to setting up their own camp to engaging in activities for the very first time — like river kayaking — the whole experience promoted a ton of learning and growth. And most of all, Amelia simply loved it. She was beaming when we picked her up and couldn't stop talking about the group's different routines and adventures. Thank you so much for this invaluable experience."

Katie Madrigal

Williamstown, Massachusetts

"Thank you Overland for being an integral part of our children's growth and perseverance over the last 10 years."

Janice Beckman

Summit, New Jersey

"Just a short note of gratitude for an absolutely spectacular summer for our Olivia on Mountains & Sea Adventure. She had a life-changing experience, all to the credit of her outstanding leaders Belle, Adam, and Ronan who created a culture of friendship and positivity and optimism that honestly has impacted Olivia for life. I can’t say enough about how much her experience meant to her. We will be back next summer. Extra thanks to special leader Adam who connected with Olivia in a magical way. We are forever grateful to Overland."

Rachel Steel Cohn

Westport, Connecticut

"We were thrilled with the experience. Sunny came home happy and proud. In just a week’s time, we felt a tangible shift — she’s more confident and sure of herself. Her counselors were lovely, and Sunny’s already asking to do a two-week trip next year!"

Ashley and James Cart

Williamstown, Massachusetts

"I had a lot of apprehension whether Finn could handle this trip — so much outside his comfort zone. He had so much fun! Learned a lot and learned a lot about himself. He seemed more confident when he came home. There is not enough I can say about how happy we were with everything. [His leaders] Frank and Marisa were incredible — and the Overland staff really helpful (allergic reactions, travel delays). The experience was transformative for Finn. He is different — himself but a better version."

Katie Heller

West Hartford, Connecticut

"Exceeded our expectations. This was the first experience of this kind for my daughter. She is a beginner hiker, and she said the experience was just amazing. Leaders were nurturing, knowledgeable, and relatable."

Kim D’Abreu

Washington, DC

"I would recommend an Overland trip to anyone! Every person I have had the pleasure of dealing with is kind, helpful, genuine, and they truly care about ensuring the experience is positive. I wanted a camp that focuses on exploration both outdoors and self-exploration — Overland was amazing! Grant will be back next year!"

Deanna McBoyle

New York, New York

"I tried not to have any expectations — I just wanted her to be safe and happy. That she was! Thanks for the professional, simple, and clear communication, the pictures, and the itinerary. I would highly recommend Overland to others."

Jenni Clock

Marblehead, Massachusetts

"This is Paige's fourth Overland summer, and she returns home with so much confidence and positivity and growth experience that she carries with her throughout the year!"

Meredith Asplundh

Princeton, New Jersey

"James' Overland trip was the highlight of his summer. He spent weeks getting his gear together, taking training hikes, and packing. James is a pretty self-sufficient, resourceful, and independent young man, but the experience at Overland this summer really elevated his confidence, his ability to interact with and work with his peers, and his knowledge of the outdoors. When James returned home he spent hours showing us photos and telling us all about his trip. James wrote a few really wonderful essays about his experiences. Thank you again, especially to the trip leaders who dedicated their summers to giving my son and the other young people such a growth experience."

Thomas Gnecco

Washington, DC

"This was an exceptional trip for Mary. She knows she can do anything she puts her heart into, but climbing Mt. Kilimanjaro and summiting is an amazing feat — Thank you!!"

Emily Baillos

Winnetka, Illinois

"This is such a quality organization, and Stuart grew so much from this trip. Despite the fact that it was only two weeks, it seemed like he matured years. His coaches and teachers have commented on this as well. Plus, he eats all sorts of food he wouldn't have tried otherwise. The best thing was when he said the thing he learned most was that the best way to get over feeling homesick is to laugh. So many life lessons he learned thanks to all of you!"

Laura and Stuart Strong

Concord, Massachusetts