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.

Mountains & Sea Adventure

Spend two weeks exploring New England—from the lakes and mountains of New Hampshire to the bike paths and beaches on Martha's Vineyard.

Two weeks packed with friendship and fun.

Swim in Lake Sunapee and hike Mount Monadnock (and enjoy a six-state view from the top). Explore Edgartown, splash at South Beach, and sea kayak quiet bays on the Vineyard. End the trip on a high note with rafting on the Deerfield River. This summer, join Overland for two weeks of adventures in New Hampshire, plus beaches and car-free bike rides on Martha’s Vineyard!

Our trip begins in Williamstown, Massachusetts, with a short afternoon hike to stretch our legs and get to know each other. Then, we’ll travel to New Hampshire’s Lake Sunapee region for hiking, swimming, and camping. Our challenge hike up Mount Monadnock offers a rewarding six-state view from the summit.

We’ll head south to Martha’s Vineyard where we’ll bike around the island on bike paths, visit bustling Vineyard Haven and classic Edgartown, and enjoy picnic lunches and afternoons at the beach. A highlight of our time on the Vineyard will be an afternoon exploring by sea kayak as we paddle quiet bays and coves.

On our last day together, we’ll enjoy a day of rafting on the Deerfield River and then return to Williamstown for a final celebratory dinner, where we’ll look back on two weeks of adventure and accomplishment, friendship and fun.

Mountains & Sea Adventure is a wonderful introduction to exploration and adventure in a supportive, wholesome environment, capably led by caring Overland leaders, with activities carefully calibrated to the interests and abilities of 4th, 5th, and 6th graders.

Good Things to Know. The group is always small — no more than 12 students — and we always have carefully chosen and thoroughly prepared leaders. The itinerary is crafted to provide just the right mix of activities — the goal is to have every student love their Overland experience. The camping is in private campgrounds and state parks, all of which offer full facilities, including hot showers. Meals are wholesome, nutritious, and varied… and they’re fun group projects with input from everyone and guidance from the leaders. Getting to and from the trip is a breeze: Williamstown is Overland’s home base with easy (about three hours) access to Boston, Connecticut, New York, and New Jersey… and there are good flight options from around the U.S. on United, American, and Southwest into the Albany, New York, airport (an hour away… and we provide a supervised shuttle both ways).

Have a question about availability?

Contact Us or call: (413) 458-9672

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Overland offers introductory, hiking, language, and service programs domestically and abroad for students in 4th through 12th grade.