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.


Jacklyn Matts

Director, Technology & Development

Email Jacklyn

As a technology evangelist, I’m focused on how people experience and either benefit from or struggle with the systems they use each day.

When I was 14, I wrote my first piece of software. It was a catalog of plant species for my mom’s landscaping projects. Writing code came naturally, but the look of wonder and delight on my mom’s face when her ideas were transformed into something real and useful — that’s the reaction I chase with every project.

I’ve consulted on several projects with Overland in the past and was delighted when offered the opportunity to take a more direct role within the organization. The focus on team-building and leadership development built into each Overland trip is clearly evident among the office staff and just one of the things that made me feel like Overland would be a great fit.

It’s been rewarding to work with each team at Overland, developing solutions that meet varying challenges while maintaining a consistent, cohesive flow of information throughout all the processes that converge each summer. I like to think my software frees my coworkers from the mundane and allows Overland to focus on what’s truly important — providing engaging and rewarding experiences for each student every summer.