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.

Haley Chelsvig Banner

Haley Chelsvig

Hometown: Jacksonville, Illinois
College: Drake University

In 2014, I studied abroad in New Zealand and went on my first tramp (backpacking in New Zealand); it was then that I discovered the joy of carrying everything I need to survive on my back.

Originally from Jacksonville, Illinois, I graduated from Drake University in 2016 with a degree in biology and psychology. At Drake, I took a class on how to run national parks in a sustainable manner, which took me to Rwanda, Kenya and Turkey. After graduation, I moved to China to teach English language and literature classes at Guangxi University in Guilin, China. After returning from China, I taught eighth grade science as well as outdoor education and leadership at The Outdoor School in Texas and Frost Valley YMCA in New York State. Currently, I teach outdoor skills at Conserve School in the Northwoods of Wisconsin, a semester-long immersion in environmental studies and outdoor activities which deepens high school students’ love of nature and reinforces their commitment to conservation. I teach students everything they need to survive in the woods — from starting a fire to using a map and compass. I also teach them how to belay, mountain bike, cross country ski, as well as many other outdoor activities. In my free time, I enjoy traversing through the Sylvania Wilderness on backcountry skis; the silent snow-covered forest teaches me something new each time I visit. I also love bouldering and am training to compete in a triathlon.

In 2019, I led Alaska Challenge. Leading for Overland is so fulfilling because I see the students transform in front of me. Their hard skills mature, and their self-confidence grows. From watching groups come together over long days of hiking to cook-off competitions at camp, it’s a joy to witness the creativity, leadership, and teamwork Overland students bring to their trips.