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.
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.
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).
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.
Join us for a summer outdoors with friends that's long overdue!
Carefully Crafted Trips
Every Overland trip offers friendship and fun, laughter and stories, adventure and exploration. With carefully planned itineraries, thoughtfully calibrated challenges, and clearly defined goals, our trips capture our students’ imaginations, stretch their abilities, and strengthen their bonds with one another.
A World Full of Promise
Optimism. Enthusiasm. Joy. That’s what you see and hear and feel at Overland. In everything we do, we seek to inspire our students to see for themselves the world’s beauty and promise.
More Than Just a Summer Experience
Whether it’s a lifelong friendship, a trove of joy-filled memories, or a spirit-sustaining love of the outdoors, Overland is more—much more—than just a moment in a young person’s life.
A bike, a small group of friends, and the span of a whole country disappearing beneath his tires instilled a desire in Tom Costley to provide similar growth experiences to youth.
Learn More about Us
Overland’s leaders are terrific role models for our students. Capable and caring, our leaders focus on creating supportive, wholesome environments where every student can flourish and grow.
Meet Our Leaders
Our groups are limited to 12 students — we pay attention to age, grade, gender, the mix of hometowns and schools, and we limit friend pairs to no more than two per group.
Why Small Is Better
We expect a lot of our students — from playing by the rules to including everyone and helping out. At Overland, we value a positive attitude, enthusiasm, and consideration for others.
High Standards Matter
Friday, January 29, 2021 Our wild admissions ride continues! This year’s flow of applications matches, and in many cases exceeds,...
Friday, January 15, 2021 Wow! What a week it's been. Admissions is 75% ahead of last year on a day-to-day...
Overland's Trip Planning team—Meg Pritchard, Will Parmacek, Dave McCahill, and Ben Grannis—recently shared their thoughts on Overland’s 2021 plans with...
Overland's founder and director, Tom Costley, recently chatted with Beth Larcom and Luke Costley, the Overland leader hiring team, to...
Overland's founder and director, Tom Costley, recently sat down with the Overland Admissions Director, Emily Ferrell, to discuss her leadership...
The Overland team is planning, preparing, and eagerly awaiting summer 2021. While we can’t predict what the coming months will...
Overland’s mission is rooted in respect for others. We are committed to a world in which every person is seen,...
At Overland, we have always known that it is the people who make this community so special. In recent days,...
Last week, our Founder and Director Tom Costley shared his reflections on the Overland tradition of Dessert Circle. Overwhelmed by...
Tom Costley, Overland's Founder and Director, reflects on the origins of the Overland tradition of Dessert Circle. I don’t know...
Last week, those of us in our Williamstown office made the adjustment to... not being in the office. On Monday,...
Meg Pritchard, a member of our year 'round team, shares some reflections on Overland in these unprecedented times. At Overland,...
If you leaf through the pages of the Overland catalog, you’ll get inspired to do something epic. The picture of...
Writing & Hiking and Language & Hiking trips have the same essential Overland group experience within the context of building confidence in the classroom.
Read about our Operations staff and the care and attention that goes into every detail of a trip.
Overland is a bit different than traditional summer camp. Instead of returning to the same place with the same people...
The Land of Fire and Ice! Travel to the southern coast to hike past thundering waterfalls and raft the Gullfoss Canyon.
Learn more about our trips for our youngest students, grades 4-7.
Follow one of our Alpine Challenge groups as they hike from one campsite in Stechelberg, Switzerland to a hut in the Alps.
Since Overland's first (and only) trip in 1985, we have expanded across the globe, but our core values have never wavered.
Follow our cross country bike trip on their 111-mile ride across the Mojave Desert and all the way to the Pacific Ocean.
When the Selingers invited Overland founder Tom Costley to give a slideshow back in 1984, they probably didn’t think their...
Completing the American Challenge — biking for six weeks and 3,000 miles across the United States — is a heroic...
One of the most challenging things I’ve ever done was on an Overland trip. On Canadian Rockies & Montana in...
Every evening, on every Overland trip, students and leaders sit down (with a sweet treat, of course) to recap the...
It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an...
Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a...
As any Overland student knows, preparing for your trip can be a bit nerve wracking. Whether you’re embarking on Berkshire...
