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.

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Hayden Gillooly

Assistant Director, Admissions

Email Hayden

My friends call me a world-traveling-homebody.

I’ve been fortunate to have the opportunity to circumnavigate Puerto Rico on a tall ship and to explore the wonders of the Bahamas, Spain, Colorado, and the Republic of Georgia. I’m invigorated by exploring new places but I’m equally content sharing a bonfire with friends in my backyard.

As an Overland student, I admired my leader’s intentionality in bringing us outside of our comfort zones in a warm, welcoming environment. My love for being outdoors followed me to college. I studied Geosciences at Williams College. Upon graduation, I spent the summer leading Overland students on Rocky Mountain Explorer. Summiting our challenge hike, Mt. Elbert, filled me with an overwhelming sense of pride in how much my students had grown in just two weeks. It was a special moment to embrace my group, with tears of joy in our eyes, overlooking the landscape of majestic mountains. My students inspired me to say ‘yes’ to adventure each day, whether it is completing a polar plunge in Snow Lake, swimming down the Arkansas River, or dancing in the pouring rain.

I feel thankful to be a part of such a passionate community. I love that my work allows me to help students dream up summer adventures filled with awe-inspiring vistas, new friendships, teamwork, and a greater appreciation of our world.