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

Explore the best of New England by foot and kayak.

Two fun-filled weeks outdoors!

Explore Massachusetts’ Berkshire Hills, Vermont’s Green Mountains, and New Hampshire’s White Mountains.

Designing a two-week hiking trip is simple, really. First, we consider the students: many are first-timers at this kind of thing. So we calibrate the trip and pace appropriately. Then, we need a beautiful area to explore. New England Explorer hits the mark in all these ways — good for first-timers, just the right pace, and a beautiful place. See, it’s simple. Really.

Start with day hikes. No heavy packs — just lunch and water — and a reasonable goal. On New England Explorer, we start in the Berkshires and the Green Mountains, where green hills become rounded peaks, and there’s a perfect balance of challenge and fun. Then head to New Hampshire’s White Mountains — craggy, handsome peaks with a rich and storied history — for three days of backpacking.

Summit the three highest peaks in three different states. Tackle Mount Greylock — Massachusetts’ iconic climb that reaches 3,491 feet. Take on Vermont’s 4,395-foot Mount Mansfield — still a day hike, but higher, and longer. Top it off with a hike to the summit of Mount Washington. At 6,288 feet, it’s the highest point in New England — a great adventure and an ideal challenge.

Then mix it up and try something new. Head to the coast of Maine for two days of sea kayaking. Paddling is a great way to explore the area, offering a close look at the bays and islands of this famous coastline.

At trip end, celebrate everything — the adventures and accomplishments, the friendship and fun. Now that’s a nice trip.

Have a question about availability?

Contact Us or call: (413) 458-9672