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.

Open Arms Leader Fellowship

Overland is committed to broadening access to its programs for students and leaders alike.


In 2021, Overland introduced the Open Arms Leader Fellowship to leaders who self-identify as BIPOC (Black, Indigenous, and People of Color), LGBTQ+ (Lesbian, Gay, Bi-Sexual, Transgender, Queer), from a low-income background, and/or other marginalized identities. The fellowship provides additional financial support for qualifying leaders as a way to promote diversity, equity, and inclusion among our leader staff.

Now in its fourth year, the Open Arms Leader Fellowship has been extended to over 100 Overland leaders, culminating in approximately $100,000 distributed to qualifying staff members.

Why It Matters

BIPOC, LGBTQ+, and people from a low-income background traditionally are under-represented in jobs in the outdoor industry. The Open Arms Leader Fellowship recognizes the need for increased representation and access to jobs for people in these demographics.

  • Representation matters and makes a difference in the experience of our students and fellow leaders. Our staff should reflect the growing diversity – as it relates to race, ethnicity, gender expression, and sexuality – of our student body and the world we live in.
  • Socioeconomic status should not be a barrier. Overland needs to do what it can within the framework of our industry to increase access to the outdoors.

How It Works

Applicants should indicate on their application that they would like to be considered for the Fellowship. Returning leaders will be able to express interest in the Fellowship on their Leader Portal. The Fellowship will be granted on a discretionary basis as part of the leader’s employment package.

The Fellowship includes up to $1,000 in additional financial support. These funds may:

  • Cover 100% of the cost of travel to and from Williamstown for Leader Training and Closing.
  • Cover personal gear costs (i.e. hiking boots, a raincoat, a headlamp, etc.) beyond what Overland offers to staff on loan for the summer (i.e. tent, sleeping bag, sleeping pad, backpack).

Applicants and returning staff can expect to receive detailed information related to the Fellowship in addition to their offer letter and at-will employment contract.