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

Clay Andreen

Hometown: Nashville, Tennessee
College: Washington University in St. Louis

As a student at Washington University in Saint Louis, I was given the opportunity to travel to Madagascar in 2018 to further my passion for the outdoors and to work on a sustainability project, alleviating pressure on the local rainforest.

Originally from Nashville, Tennessee, I graduated from WashU in 2019 with a double major in finance and economics as well as a minor in computer science. I am passionate about the intersection of business and technology. As a student, I consulted for a few nonprofits in the Saint Louis area, and I am currently working at Capital One in Washington, D.C. An avid sports fan, I played on a club ultimate Frisbee team in addition to playing intramural sports at WashU. My senior year, I joined two different Latin dance groups, focusing on learning Salsa, Bachata, and Tango, and I performed in cultural shows and other expos. In my free time, I love playing guitar and ukelele and exploring the beautiful trails in the local state parks.

As an Overland student, my trips gave me a larger understanding of the world while also fostering confidence. Whether it was cooking fried chicken with three other people on my trip; hiking Cotopaxi, a stratovolcano in Ecuador; or relaxing on the beach after a long day of farming, each experience I had helped shape me into the man I am today. In 2017, I led New England Adventure and North Country Adventure, and in 2019, I led Sierra Explorer. I enjoy leading trips similar to the ones I experienced. I hope to be a catalyst for growth in each student’s life.