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 #2: January 29, 2021

Discovery & Inspiration


Friday, January 29, 2021

Our wild admissions ride continues! This year’s flow of applications matches, and in many cases exceeds, the best years in our nearly forty-year history.

And, here’s what we’re hearing from families day after day: now, more than ever, a summer outdoors–with new friends, exploring the world’s beauty–is essential.

We couldn’t agree more.

For our 5th and 6th graders, what could be more fun than exploring Yosemite National Park with eleven new friends (and two amazing leaders)? We think, not much.

And, to make it easier for our families to plan with confidence, we’ve taken some important steps this week:


We’ve made all payments fully refundable until Saturday, May 15.


With travel abroad still an uncertainty for this summer, we are now providing all of our students enrolled on international trips the option of reserving a backup spot on a U.S. trip.

Teens hike in the woods while on their summer adventure trip
Games and riddles, songs and stories make the time on the trail one of the best parts of our trips.


As we plan for the summer, we know that our existing trip structure is ideal:

  • Small groups (twelve students and two leaders)
  • Outdoor settings
  • Limited contact with the general public

In addition, this summer we will:

  • Treat our groups as family units / pods
  • Maintain social distance and wear masks when near the general public
  • Require a negative PCR test before trip start
  • Encourage smart air travel practices (for example, wear N95 masks in airports and on board)

We will continue to refine these policies as summer approaches, always with the goal of taking a thoughtful, commonsense approach to maintaining our students’ health and well-being.

1 CA1
A triumphant end to the summer: your challenge hike or ride will push you, bring your group together, and make you realize just how much you can accomplish when you work together.


Apply today. Let us get to work finding a great spot for your child for this summer. After a long year of remote this and Zoom that, a summer outdoors, with friends, exploring the world’s beauty is essential.

Tom Costley is Overland’s founder and director. After graduating from Williams College, Tom spent a summer biking across the country– despite never having bike toured before. These days, Tom spends plenty of time on the road– including helping out with desert support for our American Challenge trip. While he still prefers two wheels to four, even he has to admit that a Jeep with an Overland banner looks pretty, well… cool.

Overland Banner

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