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.

There’s Beauty Out There

Discovery & Inspiration

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

It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an onslaught of negative attitudes overwhelm us daily. It can feel inescapable — even (or especially) to kids. When I was an Overland student, I needed to get away from it. I craved that escape.

Teen ride bikes through a forest of redwoods taken from above.
Biking through the Redwoods

Over five summers and five Overland trips, I was reminded of the joy that is so often drowned out by everything else. On the Pacific Coast bike trip, Oregon and Washington showed me some of the most beautiful scenery I’ve ever encountered. Not from the backseat of a car, but on the saddle of a bicycle. On California, I biked across demanding terrain through vineyards and redwoods which reminded me of the satisfaction and growth one finds in hard work and persistence. And on Canadian Rockies & Montana, I built meaningful friendships in just two weeks as we relied on each other to complete one of Overland’s most challenging trips — steep mountain passes, glacial lakes, and 70-mile days on our bikes.

Overland kids pose together in front of a Maine lighthouse during their summer adventure.
New England Explorer Lighthouse

These teen summer adventures instilled in me values that are now core to who I am: teamwork, selflessness, leadership, optimism. They also taught me the importance of unplugging from social media, remaining present, and holding myself to the highest standard while encountering new challenges.

Since those five summers, I’ve worked for Overland as a trip leader and Operations Team member. At last year’s Leader Training in Williamstown, founder Tom Costley said, “The world is a beautiful place. We’re going to remind our students of this — we’ll help them see how beautiful, exciting and full of promise the world is.” Reflecting on my experiences as an Overland student and leader, I’m grateful for that attitude. Knowing that there’s so much promise — in nature, in teamwork, in perseverance — inspires me to relentlessly seek beauty out. I look for it every day, and Overland has taught me the importance of sharing beauty with others.

Two leaders pose in front of mountains, with the female lead on her male coleader's shoulders holding a sign reading Overland.
Smiles on Northwest Expedition
A hiking group poses on a ridge in the Sierra Mountains during their most challenging hike of the summer.
Sierra Explorer Grandeur

Filed Under: Teen Summer Adventures / Teen Adventure Programs / Summer Hiking Trips

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