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.

New England Explorer

Hike, backpack, and sea kayak the best of New England!

Three fun-filled weeks outdoors!

We’ll start with day hikes in the Berkshires and the Green Mountains, then head to New Hampshire’s White Mountains for three days of backpacking. Over the course of the trip, we’ll summit the three highest peaks in three different states: Mount Greylock, Mount Mansfield, and Mount Washington. In Maine, we’ll sea kayak on the coast and explore more hiking trails, including three more days of backpacking in Maine’s vast wilderness. At trip end, we’ll celebrate everything — the adventures and accomplishments, the friendship and fun. Now that’s a nice trip!

Download the
New England Explorer Itinerary
for all of the details!
"My leaders were the best! They were always there to support me and cheer me up. I also really enjoyed hiking Mt. Washington! Getting above the tree line was a blast! "

Kate R.

New Jersey

"Jared came home enthusiastic and with lots of stories to tell. He clearly grew from the experience, and he's especially proud to have hiked the highest peaks in Vermont and New Hampshire."

Allison and Jason R.