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.

Looking Ahead: 2021 Perspectives from Admissions

Teamwork & Leadership

An introductory summer hiking trip

Overland’s founder and director, Tom Costley, recently sat down with the Overland Admissions Director, Emily Ferrell, to discuss her leadership of the admissions team’s efforts for teen adventure trips in summer 2021. Read our current COVID-19 policy here.

Tom Costley: What are Overland families most looking forward to next summer?

Emily Ferrell: There’s so much families are looking forward to this summer! A lot of our students are excited about getting outside, and being with peers. I think they’re excited to travel and to hike and bike. But, they’re most excited about meeting other students and making new friends.

Parents have told me that they’re looking forward to their children being able to step away from their screens, and not spend days sitting in front of Zoom classes or on social media.

And, I’ve also heard from families who are planning family trips to coordinate with their children’s Overland trips. For example, one family is planning to drop their child off at the start of their Overland trip in Portland, Maine, and then spend some time bicycling the Maine coast. Another family is packing up their Sprinter van and hitting the road this summer. They plan to spend time in Jackson, Wyoming, while one of their children does a hiking trip with Overland, and after her trip finishes they’ll drive to California to watch their older child finish Overland’s American Challenge cross country bicycle trip.

Emily, who lives in Boulder, Colorado, gets out on the water

Tom Costley: While acknowledging the likelihood of widespread –if still not universal– vaccinations for COVID by the end of June, what advice are you giving families as they make their Overland plans for the summer?

Emily Ferrell: Regardless of the year and circumstances (even as unique as they are with COVID), I always encourage families to first talk with their child about where their child would like to travel this summer, and what trip they would like to do, and to touch base with us for help or guidance.

This year, I’m encouraging families to have those conversations sooner rather than later, and to touch base with us earlier than in past years. I’m doing that for two reasons.

First, we’re seeing trips fill much earlier this year than in past years. Some trips are already full, and others are nearly full. We put so much time and energy into building groups, and in some locations we’re limited by permits, outfitters’ availability, and other external influences. In many cases, once a trip fills, there’s nothing more we can do to create additional space. If a student has their heart set on a particular trip, I don’t want them to miss out by applying too late.

Secondly, all payments for an Overland trip, including the deposit, are fully refundable until April 1, 2021. I love this because it gives our families an additional bit of flexibility. We realize there’s a lot of uncertainty, and this flexibility at Overland allows a family to grab a spot on a trip for their child while continuing to sort out summer schedules.

Every Overland trip has a clear goal– like crossing the Golden Gate Bridge by bike!

Tom Costley: Does the pandemic offer any silver linings in terms of admissions?

Emily Ferrell: Absolutely. Every winter we see students begin to get really excited about their summer trips. This year, though, because 2020 trips were canceled due to the pandemic, some students have been waiting an entire year to get out on their Overland trip. By the time June 2021 arrives (in just a few short months) our students are going to be more than ready to get outside! I think we’re going to see students who, after a year of remote learning, distance from peers, and a lot of time at home, are excited and incredibly appreciative of the opportunity they have to travel, try new activities, and spend time with peers.

In fact, I think that will be the case for our leaders and all of us on the year-round team, as well. This summer will feel extra special, because we will all truly appreciate what a gift it is to be able to travel and spend time with others.

Emily and her rescue dog, Peanut

Tom Costley: When you’re talking to a prospective family, what are your goals?

Emily Ferrell: First and foremost, I want to learn about the family and the student. I want to understand what the student is looking for in their Overland experience. There are so many wonderful trip options, and sometimes it can be overwhelming for a family to sort through. I love having conversations with families, to learn a bit more about their child: what their child’s interests are, what activities they enjoy, where they’re excited to travel. From there, I have a better sense of the child and can recommend some trips for families to consider. I want to make sure we work with a family to find the best fit for their child.

Tom Costley: Anything else to add?

Emily Ferrell: This year, more than any year in the past, I’m looking forward to the summer.

I can’t wait for our students to get out there – to the White Mountains in New England, the Alps in Switzerland, and the Rockies in Colorado – and have fun. Every summer, I love hearing stories – from leaders, students, and parents – about all of the trips. And, I can’t wait to see the photos from all the trips!

Tom Costley is Overland’s founder and director. After graduating from Williams College, Tom biked across the country– and in doing so experienced the senses of purpose, teamwork, and friendship that would become Overland’s bedrock values. This past summer, Tom took the opportunity to “bike across the country” again, this time completing 3,150 miles of riding around his home of Williamstown, Massachusetts. 

Tom’s the one who’s not wearing an Overland jersey. His great friend Spike is on the right. Here, they’re celebrating the end of Tom’s 2020 “cross-country” ride with a dip in a Vermont lake.

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