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.

Bridget Whalen Banner 1

Bridget Whalen

Hometown: Raleigh, North Carolina
College: North Carolina State University

As a student, I participated in five Overland trips — Blue Ridge Explorer, Rocky Mountain Explorer, Alaska Explorer, Appalachian Trail Challenge, and the Teton Challenge.

Originally from Raleigh, North Carolina, I graduated from North Carolina State University in 2016 with a degree in elementary education and a STEM concentration. While at NC State, I student taught in a number of schools and age groups. During my senior year, I taught fourth grade full time at A.B. Combs Leadership Elementary in Raleigh. Throughout college, I worked with Read to LEAD and Community Hope, volunteer programs that encourage and develop reading skills of elementary-age children from low socioeconomic backgrounds. I was nominated for an internship at the Poe Health Center in Raleigh, where I designed, updated, and implemented family health programming. During college, I assisted a local occupational therapist, teaching swim lessons to children with sensory and learning disabilities. After graduation, I moved to Wyoming to work for the Teton Science School. I was fortunate enough to work with a highly motivated and passionate team recognized for their innovation in place-based and project-based learning. Currently, I am pursuing graduate studies and teaching second and seventh grades in Raleigh. In my free time, I enjoy yoga, studio cycling, and writing.

In 2013, I was a member of the Overland Support Staff; in 2014, I led Berkshire Adventure; in 2015, I led Sierra Adventure; in 2016, I led Maine Adventure; in 2017, I led Alps Explorer; in 2018, I led Northwest Expedition; and in 2019, I led Field Studies Tanzania. I love working with adventurous, hard-working Overland students, who inspire me with their willingness to challenge themselves and build community.