Leading in the Sierras
“I love middle schoolers! They are so goofy, energetic, and eager to learn.” Overland leader Tiana took a break from...
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
Available
This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.
Limited
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.
Call
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.
Questions?
Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.
The World's Beauty & Promise: Stories from the Overland Community
Summer 2022: Admissions Update #2
2022 is off to an exciting start here at Overland! January is typically the busiest month for the Overland Admissions...
Summer 2022: Admissions Update #1
Over the past few years, we’ve been tremendously grateful for the outpouring of support from the Overland Community. This year...
The Eyes Up Ride
I started thinking about riding cross-country in January of 2021. I had been a member of the Overland year-round team...
Flying To An Overland Trip
December 1st, 2021 While backyard adventures are fun, sometimes it takes a flight across the country, or around the world,...
Looking Ahead: 2021 Perspectives from Trip Planning
Overland's Trip Planning team—Meg Pritchard, Will Parmacek, Dave McCahill, and Ben Grannis—recently shared their thoughts on Overland’s 2021 plans with...
Looking Ahead: 2021 Perspectives from Leader Hiring
Overland's founder and director, Tom Costley, recently chatted with Beth Larcom and Luke Costley, the Overland leader hiring team, to...
Looking Ahead: 2021 Perspectives from Admissions
Overland's founder and director, Tom Costley, recently sat down with the Overland Admissions Director, Emily Ferrell, to discuss her leadership...
Overland 2021
The world calls out to you. Answer that call... and take the world, with all of its incredible beauty, into your arms.
A Message to the Overland Community
Overland’s mission is rooted in respect for others. We are committed to a world in which every person is seen,...
Eight Summers with Overland
At Overland, we have always known that it is the people who make this community so special. In recent days,...
Dessert Circle (Continued)
Last week, our Founder and Director Tom Costley shared his reflections on the Overland tradition of Dessert Circle. Overwhelmed by...
Dessert Circle
Tom Costley, Overland's Founder and Director, reflects on the origins of the Overland tradition of Dessert Circle. I don’t know...
Take Time to Get Outside
Last week, those of us in our Williamstown office made the adjustment to... not being in the office. On Monday,...
The Certainty of Each Other
Meg Pritchard, a member of our year 'round team, shares some reflections on Overland in these unprecedented times. At Overland,...
5 Ways to Build a Close Team
If you leaf through the pages of the Overland catalog, you’ll get inspired to do something epic. The picture of...
Challenge, Community, & Camaraderie
Writing & Hiking and Language & Hiking trips have the same essential Overland group experience within the context of building confidence in the classroom.
A Personal Touch
Read about our Operations staff and the care and attention that goes into every detail of a trip.
The Benefit of a New Group Every Summer
Overland is a bit different than traditional summer camp. Instead of returning to the same place with the same people...
Iceland Explorer
The Land of Fire and Ice! Travel to the southern coast to hike past thundering waterfalls and raft the Gullfoss Canyon.
Introductory Trips
Learn more about our trips for our youngest students, grades 4-7.
A Day on the Alpine Challenge
Follow one of our Alpine Challenge groups as they hike from one campsite in Stechelberg, Switzerland to a hut in the Alps.
Our Story
Since Overland's first (and only) trip in 1985, we have expanded across the globe, but our core values have never wavered.
American Challenge: Final Stretch!
Follow our cross country bike trip on their 111-mile ride across the Mojave Desert and all the way to the Pacific Ocean.
Spotlight: Amy Selinger — Overland Student, Leader & Parent
When the Selingers invited Overland founder Tom Costley to give a slideshow back in 1984, they probably didn’t think their...
Tales from the AC: Our Generous Hosts
Completing the American Challenge — biking for six weeks and 3,000 miles across the United States — is a heroic...
100 Miles
One of the most challenging things I’ve ever done was on an Overland trip. On Canadian Rockies & Montana in...
Dessert Circle
Every evening, on every Overland trip, students and leaders sit down (with a sweet treat, of course) to recap the...
There’s Beauty Out There
It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an...
The Joy is in the Challenge
Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a...
Trip Start – Build-Up, Preparation, Nervousness, Excitement
As any Overland student knows, preparing for your trip can be a bit nerve wracking. Whether you’re embarking on Berkshire...