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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Julia Bergquist

Assistant Director, Admissions

Email Julia

To this day, my family still jokes about how I learned to ride a bike.

When I was three years old, I begged my parents to take off the training wheels, and my dad finally gave in and took them off. While my parents were putting my little sister to bed, I snuck outside and taught myself to ride my bike. My parents ran outside looking for me. When they found me, I was smoothly riding a two-wheeler ~ sort of. I would ride a few yards and then fall. Every time I would fall, I would say “If you fall, get back up!” and continue to ride. This attitude has imprinted on my character and has carried through as an athlete, hiking leader, and now as a member of the year-round Overland team.

After studying around the world in college, I knew that I had to find a career that puts human experience at the forefront. The summer after I graduated from Rhodes College I led the Rocky Mountain Expedition. I remember leading a group of fantastic students up a 14-er (a peak over 14,000 feet) one morning in Colorado. When the summit of the mountain was in sight, I stopped the line of students behind me and called one of my students up to the front to lead the group to the summit. That student surprised me by grabbing the hands of their peers and saying “we will all summit together”. From that moment on, I knew I had to work for this company full time.

I’ve always enjoyed storytelling. At Overland, I have the unique opportunity to create new experiences for students and leaders to add to their life stories. My favorite part of my job at Overland is to hear the stories from students and leaders after their trips. It is so satisfying to know that my work directly affects and contributes to new experiences that turn into incredible stories to tell.