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.

Admissions Availability Update #1: January 15, 2021

Discovery & Inspiration


Friday, January 15, 2021

Wow! What a week it’s been. Admissions is 75% ahead of last year on a day-to-day basis. We processed over one hundred applications on Sunday alone (and had another forty-five waiting for us by 8:30 Monday morning!).

How to explain it?

Our Admissions Director, Emily Ferrell, says she hears excitement on the phone and eagerness on our Zoom Q&As:

“Families are eager for their children to have the Overland experience: small groups, outdoors, with leaders who are terrific role models. After a long year of remote learning and lives tethered to screens, the prospect of a summer of friendship and adventure in a supportive, wholesome group is powerful.”

Emily Ferrell Peanut
Emily and her dog Peanut enjoy climbing mountains and trail running when they’re not placing students on trips. While Emily travels back and forth between Boulder, Colorado, and our Williamstown office, Peanut makes his full-time home at the foot of the Rocky Mountains. He’s waiting for Overland to offer canine summer adventure trips.

How has Overland’s admissions team handled the surge in applications?

Again, Emily Ferrell: “We’re going to review each application carefully and partner with the family to find the best fit. It’s a slow, painstaking process, but it’s worth it.”

Which trips have been most popular?

“We’ve seen demand for trips in all locations and across all grade levels. Some of our most popular trips are Mountains & Sea Adventure, Rocky Mountain Explorer, Alaska Expedition, and Nova Scotia & Acadia.

Will there come a point when trips will fill?

“Yes,” Emily says, “and for some trips we’re already there—or close to it.”

Final thoughts?

Apply today. Let us get to work finding a great spot for your child.”

Tom Costley is Overland’s founder and director. He and his wife Liz have two children, both of whom participated in the American Challenge cross-country bike trip. While Tom spends most of his summer on the administrative side of Overland, when his kids were on trips, he was just like every other parent: sending letters to mail stops, cheering on his children’s accomplishments, and eagerly awaiting their reunion at trip end. Oh, and doing their laundry when they got back home!

Costley Family
Here, the Costley family celebrates the end to Luke’s American Challenge at the Santa Monica Pier.

Similar Blog Posts

Three girls carrying their sleeping bags as their summer trip begins.

Trip Start – Build-Up, Preparation, Nervousness, Excitement

Teamwork & Leadership

As any Overland student knows, preparing for your trip can be a bit nerve wracking. Whether you’re embarking on Berkshire...

Teens pose after biking across the country on a teen summer biking trip

The Joy is in the Challenge

Independence & Self-Reliance

Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a...

A girl smiles while riding her bike and wearing a helmet in front of a hill covered in pine trees.

There’s Beauty Out There

Discovery & Inspiration

It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an...

All Blog Posts