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.

Leader Recruitment: Meaningful Moments on the Road

Discovery & Inspiration

Our Leader Hiring team spent their fall season on the road recruiting new Overland leaders from around the country. Campus visits and presentations are important ways for our team to meet new potential leaders, connect with alumni staff, and stay present on college campuses across the country. From Maine to California, Colorado to Tennessee, our team traveled around the country to connect with potential Overland leaders and alumni on their college campuses. 

We sat down with @Beth Larcom, @Will Savage, @David Dustin, and @Lilly Bianchi to discuss their experiences on the road. Our team is excited to share stories of meaningful moments full of enthusiasm and promise for the summer ahead. 

Our leaders travel to Williamstown, MA each summer to gather for two weeks of leader training.

Julia: When reflecting on your time on the road and campus, is there a meaningful moment that stands out to you?

Beth: One moment that stands out, in particular, is from our visit to Tufts University. Tufts was one of our first visits, and I was overwhelmed by the student excitement to see us. We sat in the student center (with copious amounts of donuts), and talked to so many amazing young people. Whether they knew Overland well or not, it was great to connect with so many students. It was especially meaningful because we hadn’t been in person on college campuses in nearly two years – to feel the energy in the room was fantastic.

Lilly: It was meaningful to reconnect with a former Overland leader and friend of mine, Madeline, whom I met way back in 2017! David and I had dinner with her in New Haven, which was a blast. It was fun to catch up and heartening to hear her reflect on her time with Overland over a slice of pizza. She described her summers leading as “the most formative work experience of her life,” and I couldn’t agree more. It’s always nice to be reminded of Overland’s magic, both in the lives of students and leaders.

Spending eight weeks of your summer in a beautiful place, with eager and excited students, and a supportive co-leader is an experience of a lifetime!

Julia:  It’s always exciting to visit past and returning leaders on their home campuses. What was it like seeing familiar faces outside our Williamstown base?

Beth: It was wonderful to see our leaders in their element on their college campuses. When leaders are here in Williamstown, they are out of their comfort zone a little bit – they are away from home and away from their familiar spaces. When we see them on campus, they are fully at home. They show us around with so much joy and we catch up over a meal in town. They often show us around and share their lives on campus with us, and we are so grateful for their warmth. We can’t wait to see more of our leaders out and about this spring!

Our hiring team often has dinner with alumni leaders on campus to connect during the school year.

Julia: When scheduling school visits, what went into your consideration? What are Overland’s goals when it comes to campus outreach?

David: One of our foremost goals is to make Overland a familiar name. We make multiple efforts to accomplish this: tabling, sending posters to campuses ahead of time, holding info sessions, and spreading the word through local staff and campus contacts. We know it’s not always the first encounter with Overland that leads a person to apply; rather it’s the accumulation of several positive interactions. Although Overland is already a household name at several schools, we’re committed to fielding a diverse leading staff; therefore, we’ve made it a priority to go places we haven’t gone before. By literally meeting prospective leaders where they’re at, we hope to make ourselves accessible to folks who might never encounter us otherwise.

Each summer, about half of our leaders are new to Overland.

Julia: This year, our leader hiring team visited their alma mater schools. What was it like to return to campus for Overland recruitment?

Will: Exciting! I’m a huge fan of my alma mater, and I constantly talk about Bowdoin. Having graduated in 2021, I’m still connected to campus. Returning to friends and professors at the school made me feel right at home during the recruitment process! Whether it was connecting with people from the outing club, classroom, or frisbee team, I called on those individuals to encourage their students, teammates, and peers to apply to Overland, and so far it appears to be working! Of course, being able to give a tour of Bowdoin to one of my colleagues was invaluable in continuing the process of building a tight-knit year-round Overland team. It was great to share some of my favorite places with them. If anyone ever wants to talk about Bowdoin or Maine, feel free to call our office and ask for Will!

Will Savage playing frisbee with his students on Alaska Explorer in 2021.

Julia: Lilly, growing up as an Overland student, leading Overland trips in college, and now recruiting leaders full-time, how does this Overland experience shape your perspective on leader hiring? Did you have a chance to meet past Overland students while recruiting this season?

Lilly: I feel pretty lucky to have seen so many aspects of Overland, and those experiences certainly shape my approach to leader hiring. As a student, I loved all of my leaders and all of them were unique. Some were loud and gregarious, and some were quiet, but all of them seemed like superheroes. When I started leading, I realized that you don’t need superpowers but instead commitment and a love for what you’re doing. These memories are a great reminder that there’s no one type of great Overland leader. It’s a pretty cool full-circle moment for me and I’m not sure that younger Lilly would quite believe it. 

Meeting past Overland students was one of my favorite parts of traveling this fall! Everyone remembers their trips so fondly, and it was lovely to hear folks talk about their favorite moments even if it had been five or six years since they had been on a trip. I think we met at least one former Overland student at every campus I went to. 

Lilly Bianchi (second from the right) connects with her fellow St. Lawrence alumni at leader training.

Julia: Any other stories from the road? 

David: When we were visiting Elon, the outdoors director invited Will and me to join an outdoors club staff meeting. My expectations were smashed to pieces when we walked into the room, and 30 students were running around, fiercely debating with each other, brandishing compasses, ropes, and notes. 

Finally putting it together, we asked, “is this an escape room?”

“Yep, I set it up with a student this evening. They have to use outdoor technical skills to get out.”

After about 30 minutes, and some accusations that we were a part of the puzzle, the club “escaped” and congregated outside for their weekly s’mores social. We had several great conversations with prospective leaders, but what struck me was the social strength of the community we had stumbled into. These people were fun-loving, expressive, and devoted to each other. The culture we each try to foster on our Overland trips was in full swing at Elon, and it reinforced my hope that we can connect with pockets of individuals across campuses who are devoted to creating the same sort of accepting, creative, fun, and challenging-hungry spaces and group dynamics that Overland strives towards.

David Dustin speaking to our leading staff.

Our leader hiring team will be back on the road in the spring to continue their leader recruitment process. We’re excited about our approaching application deadline of January 22nd! To read more about leading for Overland, check out our leader application page





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