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.

Overland & Covid-19

Discovery & Inspiration

An idyllic picture of friends on this hiking trip for teens in New England



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

Before a trip, we will ask each of our students to:

  • Reduce contact with others
  • Obtain a negative PCR test
  • Complete our Covid-19 questionnaire
  • Practice excellent hygiene while traveling to trip start
  • And, if the student is 16 or older, to be vaccinated

On arrival, given testing availability, we will:

  • Test each student with a rapid test

Throughout every trip, we will:

  • Maintain social distance (and wear masks) when near others outside the group
  • Practice excellent hygiene at all times

If a student shows symptoms of illness, we will:

  • Obtain professional medical care, and contact the family. The attending medical professional, the family, and Overland’s directors will make the decision on treatment.

And, to allow families flexibility, we will:

  • Make all payments fully refundable until Saturday, May 15

We will continue to refine our approach as summer nears, always with the goal of creating joy-filled, healthy outdoor experiences.

Everyone here at Overland is committed to supporting each of our Overland families. Please call on us with any questions or concerns you might have.

We look forward to a summer full of outdoor adventures, and we welcome your family to join us!

With our very best wishes,

Tom & Liz Costley


We’re always happy to chat!
Call 413.458.9672 or email. We’re open Monday to Friday, 8:30 to 4:30 ET.


Frequently Asked Questions

Are any trips still available?
Yes. Most trips are full, but some have scattered availability.

Will Overland offer trips abroad this summer?
As of Tuesday, April 6, we have canceled all trips abroad except Iceland Expedition for vaccinated students who are sixteen (or older). In addition, we will run two bike trips that explore the U.S. and Canada: Nova Scotia & Acadia and Canadian Rockies & Montana. If Canada does not open this summer, these trips will ride alternative itineraries in the U.S.

If I was a senior in high school in 2019/2020, can I do a trip in 2021?
Yes! Please choose any trip open to students who will complete 12th grade next spring.

Are deposits refundable?
Yes. All payments are fully refundable until May 15, 2021.

How can we contact Overland?
Call (413.458.9672) or email: info@overlandsummers.com.

Thank you for your support—we appreciate it!

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