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.

DUA Edit

Alex Dunn

Assistant Director, Trip Planning

Email Alex

Every day after elementary school, I dropped my backpack and dashed outside to the backyard.

Growing up in New York’s Hudson Valley, my parents’ backyard was an outdoor escape that always called my name. Spending time outside provided an outlet for my creative and innovative thinking. The balance of peace in nature and the thrill of exploration has always left me feeling fulfilled — my role in trip design feels appropriate because it allows me to create opportunities for students to discover the unique beauty of the outdoors.

Since graduating from High Point University, I have worked in the finance industry as a data analyst and explored a role in PR through a national agency. While my work portfolio is diverse, I have always had a passion for leading students and exploring the outdoors. In 2021, I led New England Adventure and New England Explorer for my first summer with Overland. I immediately fell in love with the community so I was back in the summer of 2022 leading Iceland Explorer. Leading trips allowed me to see the direct impact that outdoor adventures can have on students, which inspired me to become a year-round member of the Overland team.

Overland students are pioneers and leaders. As a trip planner, I am excited to witness the positive impact that genuine and joyful experiences can have in an outdoor setting. The entire Overland community reminds me how valuable loads of positivity and endless smiles are!