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.

Team leader, teen summer biking trip

Trenton Bailey

Hometown: Nashville, Tennessee
College: Elon University and Trevecca Nazarene University

At Elon University, I worked for our outdoors program as a trip leader and a facilitator for our high/low ropes course and fell in love with experiential education as I saw people overcome their fears and learn who they truly are.

Originally from Nashville, Tennessee, I graduated from Elon with my second bachelor’s degree in exercise science in 2019. At Elon, I had the opportunity to lead a hiking trip to the Grand Canyon and Joshua Tree, a sea kayaking trip in Virginia, and a rock climbing in North Carolina. Also, I led a weeklong backpacking trip for 11th graders through Inside Out in western North Carolina. In 2016, I earned my first bachelor’s degree in social justice from Trevecca Nazarene University. While at Trevecca, I was a resident assistant, president of social life for the residence hall association and vice president of social life for student government assembly. Also, I ran on the cross country team. In my free time, I enjoy training and running in marathons, going for long trail runs, rock climbing, and playing disc golf with my friends.

In 2019, I led Rocky Mountain Explorer. My last day of my summer, I was able to spend time with two of my students while looking at Longs Peak and playing games. That same day I got to help another student who was homesick, and we talked about bears for an hour because that was the only thing that would take his mind away from home. In dessert circle that night, all three students said that I was their high of the day. I didn’t realize how important I was to them in those moments, but I felt incredibly special and it made me realize how much of an impact we can have on our students.