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.

Kate Dittig Banner e1561000535746

Kate Dittig

Hometown: Warwick, Rhode Island
College: Keene State College

For the past six years, I have led adventure trips from whitewater rafting and mountain biking to backpacking and kayaking; I love helping students grow as individuals, and I enjoy learning from them, too.

Originally from Warwick, Rhode Island, I graduated from Keene State College in 2013 with bachelor of arts degrees in communications and journalism and from Clemson University in 2018 with a master’s in education and student development. In this program, we focused on how to advocate for individuals of all identities and how to empower students. At Clemson, I held two graduate assistant positions — one in the multicultural office, where I focused on LGBTQ student initiatives, and the other was a student-athlete development position, where I helped facilitate leadership academies, community service projects, and career development. Since graduation, I have been teaching outdoor education throughout California and playing outside on the West Coast. Nature is the greatest classroom, and I love instilling a passion for the outdoors with my students. In my free time, I foster puppies and pretend to know how to play the ukulele. I also love working out at the gym and scrambling eggs to perfection.

In 2019, I led Yellowstone Teton Expedition and Iceland Expedition. As a leader, I have shared so many life-changing moments with students from all around the world, and I loved my trips with my Overland students. Overland students are family.