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.

How to Choose the Right Summer Hiking Trip for Your Child

Independence & Self-Reliance


Here in the Overland Office, the wintertime is our busy enrollment season! 

That means phones are ringing and lots of folks have questions;  one of our most common questions is “what trip is best for my child?” There are lots of wonderful trips to choose from (we think they’re all great!), but we’ve got some tips below to help you find the right fit for your child. 

To get started, our website has tools to help you narrow down your search. After selecting “View All Trips,” you’ll be able to filter by grade, length, trip type, and start date. An important note here is that your child’s grade is the grade they’re currently in. 

Service trip New England summer teen
Meaningful projects on a New England farm

Depending on your child’s age, there might be a few different trip types to choose from. Hiking is central to every Overland trip, but some trip types have additional goals as well. If your child likes the sound of trail restoration or volunteering at a local organic vegetable farm, our Service & Hiking trips offer an opportunity to connect with the community, whether in New England or Alaska. Our Language & Hiking trips combine hiking in beautiful France or Spain with engaging language classes and cultural experiences. 

Perhaps the most evident difference from there is location. Where does your child want to go? Glacier-studded Alaska? The Pacific Northwest’s rocky shorelines? What about the dramatic peaks of the White Mountains? Everywhere Overland goes is beautiful and helping students cherish that is one of our goals. You can read more about what our trip planners think is a great Overland setting in their scouting reports from the Alps, the Sierras, Norway, and Spain. Ask your child what they’re most excited about because whether they’re close to home or on another continent, they’re in for a great adventure. 

Alaska’s beautiful backcountry valleys

A lot of our trips have what we call “extracurriculars,” which are activities other than hiking. Yellowstone Teton Explorer, for example, spends four days whitewater kayaking on the Snake River. Students practice new skills and progress under the careful guidance of both their Overland leaders and a number of dedicated kayak instructors. Some trips go on a multi-day sea kayak while others go whitewater rafting, and a few of our introductory trips even go rock climbing or bicycling on dedicated bike paths. These activities are one of the nuances that can help you and your child choose between different trips.

kayak the snake river jackson hole
Kayak instruction on the Snake River

Finally, there’s availability. As we move through the winter, you’ll start to see some trips’ availability turn to Limited, and maybe even Waitlist. Limited availability means that the trip is nearing full, and spots may be limited based on gender or age, while Waitlist means the trip is currently full; we’re still happy to place your child on a waitlist, and try to find a great second option in the meantime. 

At the end of the day, we want to provide choices and flexibility, but also offer trips that drive home the core tenets of an Overland experience. A parent recently said to me, “some of these trips look similar, just in different places!” That’s exactly our goal — each Overland trip has a distinct arc and a common experience of fun and challenge in a beautiful location. Choosing a trip is really just choosing a framework because every individual Overland  trip is unique. Your child’s experience will be driven by their leaders and by their group, and they’ll walk away from the summer with just as many memories of the times they laughed really hard and the creative meals they ate as they will of the mountain vistas or winding trails. 

meal prep camp backcountry
Overland is all about the group — and mountaintop lunches don’t hurt either!

Similar Blog Posts

Three girls carrying their sleeping bags as their summer trip begins.

How to Prepare For A Teen Adventure Trip

Teamwork & Leadership

As any Overland student knows, preparing for an outdoor adventure trip can be a bit nerve wracking. Whether you’re embarking...


The Joy is in the Challenge

Independence & Self-Reliance

Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a...

A summer hiking trip in Norway takes time off the trail to adventure sea kayak

There’s Beauty Out There

Discovery & Inspiration

It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an...

All Blog Posts