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.

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Will Parmacek

Assistant Director, Trip Planning

Email Will

Growing up, I loved solving puzzles, reading maps, and skipping rocks.

To my parents, it must have come as no surprise that I would soon take to exploring in the outdoors. Whether I was mountain biking, sea kayaking, or rock climbing, I was always ready for the next adventure.

As a student, I spent six summers with Overland, on trips ranging from New England Explorer to the American Challenge. My summers at Overland were easily where I was the most comfortable. Each summer, my leaders created a fun and wholesome environment, and they empowered our group to conquer our goals. In college, I knew that I wanted to provide this opportunity for kids. For the past three summers, I had the privilege of leading trips for Overland. Watching my students grow to love the outdoors and accomplish their goals was truly inspiring. As a senior at Vanderbilt, I served on my school’s Alternative Spring Break board, in which we planned 40 service trips across the country. From this experience, I developed a passion for planning trips. And so, I am excited to be a member of our Trip Planning team here at Overland.

Each morning, I wake up eager to start my day in the Overland office. Whether I am reserving a campground, ordering bikes, or talking to parents of an Overland student, there is never a dull moment. I’m surrounded by a team of dedicated, compassionate colleagues who inspire me to put forth my best effort every day. I am thankful to serve on this team, and I can’t wait for the summer!