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.

Scouting Report: The Sierras

Discovery & Inspiration

To wrap up our scouting reports series, we will take a look out west to the Sierras!

We had the chance to connect with our Sierra Adventure, Explorer, and Expedition trip planner, @Alex Dunn, and her scouting partner, @Julia Bergquist, to hear about their updates on some of Overland’s most classic hiking trips.

The trees are tall and the mountains are even taller!
Sierra Expedition is one of Overland’s oldest hiking trips starting its first year in 1992. What were your goals when scouting this fall?

Julia:  My excitement to scout for one of the oldest trips offered at Overland is through the roof! Our goal was to revisit each itinerary and gather more information about the environment around the Sierras. We visited familiar campsites, trails, and National Parks that have hosted our groups for years! It was important to take detailed notes on trail conditions, travel logistics, and group accessibility. It was easy to imagine our adventurous Overland students and trustworthy leaders in these epic places!

Alex: It’s our goal that students have a fantastic time during their adventures in the Sierras. Overland’s Sierra trips have endured the test of time. To ensure that students have just as special a time this year as they’ve had in years past, our focus during this scouting trip was to visit areas on the itinerary to ensure that they match our high level of expectations and, let me say, the Sierras did not disappoint! 

Mornings are always beautiful in the High Sierras.
Are there any changes to the itineraries? 

Julia: Our Sierra trip itineraries will stay the same. Alex and I are excited to have found fresh new day hikes to add sprinkled across to the classic Sierra’s itineraries. Our updated notes on campsites are helpful for our groups to know exactly what to expect when they arrive and set up camp. I’m most excited about one particular campsite on a crystal blue glacial lake. The tent site sits right under giant sequoia trees and the reflection of the mountains over the clear water paints a beautiful picture for our groups!

360 views from the summit ridge of a Sierra Adventure challenge hike.
What are you most excited for students and leaders to experience in the Sierras next summer?

Alex: I’m excited for both students and leaders to experience the Sierras’ natural beauty. The terrain is varied, allowing students and leaders to participate in a variety of activities ranging from hiking to rafting to kayaking. California is such a large state, and the Sierra trips allow for the groups to see so many different parts of the beautiful region.

Julia: Whether it’s the dramatic glacially cut canyons or the rugged pointed peaks, California has so much to offer for our groups. Now that I had the chance to experience the beauty of the Sierras, it’s difficult to not get excited to talk about the mountains any chance I get.

Giant sequoia trees are scattered throughout the forests.
What is your personal favorite part of the Sierras itineraries?

Alex: Challenge hikes rock! Whether you are on Sierra Adventure, Explorer, or Expedition, you are going to be in awe when you reach the peak of your challenge hike. While scouting a potential challenge hike for Sierra Adventure, Julia and I joked that the hike was uphill in both directions. While there were some challenging uphill sections, the views at the summit were well worth the effort!

Julia: The hiking is beautiful and challenging, but one of my favorite parts is how the itineraries take you into the wild. It’s true – there is nothing quite like experiencing the stars in a National Park like Yosemite. After a delicious chili dinner, Alex and I spent moments telling each other stories and reflecting on our day under the most magnificent sky. These campgrounds are incredible, and I can’t wait for our students to get as lost as I did in the beauty of the sky.

A morning sunrise at a front-country campsite near Yosemite.
What makes the Sierras special to you?

Julia:  When reflecting on my time in the Sierras, I’m brought back to our mornings at the trailheads before our day hikes. We barely parked the car, and I was already out the door; backpack on and ready to hike. I consider myself an avid hiker and have the privilege of hiking as a part of my job; however, my level of excitement and anticipation beginning each of these hikes while scouting brought me back to how it felt when I first began hiking as a student. Maybe this is your first time hiking, or maybe this is one of the hundreds of hikes you have done; either way, hiking in the Sierras will bring you joy like no other.

Alex: California has such diverse terrain. I believe that the Sierra trips provide the opportunity to accomplish great things with a special group in a beautiful place. SE

Groups follow a gorgeous waterfall up the winding trail in the southern Sierras.

Do you have any advice for students interested in going on a Sierras trip next summer? 

Alex: While a challenge hike may feel daunting because of its mileage, elevation, or simply its title of being a “challenge”, it is one of the most special and rewarding experiences on an Overland trip. On the day of a challenge hike, you have your leaders to guide and encourage you, your peers to play games with on the trail, and your personal strength and determination to get to the top! Celebrating with your group at the peak is a moment like no other. My advice to students interested in any Sierra trip next summer is to let those challenge hike nerves help push them to the top! You are going to be surrounded by supportive people who you’ll get to share a beautiful experience with.

Julia: Go all-in with your group from the start! The Sierras trips each have group challenges that will test your ability to work as a team. On one of our last days, Alex and I faced a long hiking route on a Sierra Expedition backcountry section. The clouds covered the peaks of the mountains, it was drizzling, and we knew there was a long day ahead of us. At the trailhead, Alex handed me an apple sauce and told me a story about her family. Before I knew it, we were at the top of the ridge. Of course, the view of the ridge was amazing, but what I smile about looking back on our experience was the time I had with Alex on the way to the top. So, my advice is to lean into your group members and leaders on your trip. They have some amazing stories to share!

Even the drives to and from a day of hiking are breathtaking!

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