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 Trip Planning

Teamwork & Leadership

Yellowstone Exploration

Overland’s Trip Planning team—Meg Pritchard, Will Parmacek, Dave McCahill, and Ben Grannis—recently shared their thoughts on Overland’s 2021 plans with Tom Costley, Overland’s Founder and Director. Read our current COVID-19 policy here.

Tom Costley: What are the main characteristics of Overland’s trips that make them suited to running during the pandemic?

Will Parmacek: Our groups are small and contained. We spend the majority of time outdoors in sparsely populated areas. We camp most nights and seldom pass through city centers. With some thoughtful changes, we’re well positioned to run a series of great Overland trips next summer.

Dave McCahill: The Overland experience has always been about the power of a shared experience among a small group. Our itineraries take advantage of some of the quietest, most beautiful places on Earth—with plenty of fresh air, of course!

Dave McCahill Rock Climbing Trip Planner
Dave, our European trip planner, rock climbs in the Bavarian Alps. Dave’s known for his unbelievable adventures– and also his amazing photos!

Tom Costley: While acknowledging the likelihood of widespread—if still not universal—vaccinations for COVID by the end of June, what changes—if any—do you anticipate making to your trip planning?

Ben Grannis: We’re still operating under the assumption that there will not be universal vaccinations. We’re reviewing itineraries carefully to identify areas that we can change while maintaining the integrity of the trip and activities. For instance, we are planning to avoid occasions where groups previously would be indoors or in high-traffic areas.

Will Parmacek: We’re also rethinking how we approach grocery shopping and food preparation. And for our service trips, we’re looking for projects that have less person-to-person contact. As we plan our trips, we’ll continue to follow the best available public health guidance.

Meg Pritchard: The basic structure of an Overland trip already puts us in a great position in terms of distancing, reduced public contact, and outdoor settings. Our goal is to modify our trips to adapt to a COVID-impacted world—while also retaining the aspects that make an Overland trip so meaningful.

Meg (right) most recently led Sierra Expedition in 2019, where she got to summit Mt. Shasta with 10 amazing kids. After a year living in Alaska, she especially enjoyed all the sun!

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

Dave McCahill: Of course! This has been a great chance for us to look at what moments really make an Overland trip special. Sometimes it’s surprising for us as trip planners that the simplest portions logistically—five consecutive days in the backcountry, for example—are what students rave about the most.

Will Parmacek: With COVID, we’ve been forced to rethink our trip itineraries from start to finish and reconnect with the essentials of the Overland experience.

Dave McCahill: Really, our students are just crazy about spending time together as a group—cooking, laughing, singing Taylor Swift, and climbing to the top of beautiful peaks.

Will Parmacek Hiking
While many know Will as our resident bike expert, he learned to backpack as an Overland student on Northwest Explorer. Here, he scouts our new Alaska Explorer trip.

Tom Costley: Beyond questions of adapting your trip planning to the pandemic, what are the driving forces in your planning? What are you trying to achieve?

Dave McCahill: We always approach our trips from a risk management perspective, first and foremost. We’re trying to create itineraries that are safe, but that offer an engaging experience in a wonderful location.

Meg Pritchard: We want each itinerary to have a natural progression, from the first day to the last. We want students to have fun, explore beautiful areas, and also feel a sense of accomplishment. When a trip is thoughtfully planned, it helps the group come together, provides students structure and clear goals, and allows everyone to focus on the experience.

Dave McCahill: That’s why we spend countless hours planning our trips—thinking about every mile on a bike itinerary, or which lake will be best for swimming. Really, it’s the leaders and their students who “make” the trip their own.

Ben Grannis: We want to maintain our focus on what we do best: creating incredible group experiences for students in stunning settings.

Though Ben led hiking trips for Overland, he now spends his weekends exploring Williamstown and the surrounding countryside by bike. Here, he enjoys a summer day in the Berkshires.

Tom Costley: Anything else to add?

Dave McCahill: In a sense, trip planning during COVID is a celebration of simplicity. Our goal is to provide fresh air, laughter, and great days spent outside. It’s exactly what we all need right now.

Will Parmacek: Small groups, with a focus on friends, adventure, and fun—this is the heart of the Overland experience.

Tom Costley is Overland’s founder and director. A graduate of Williams College, Tom currently lives in Williamstown with his family. When he’s not biking Vermont’s rural roads in the dead of winter (keep your eyes peeled if you ever drive through– chances are you’ll spot him), Tom loves planning bike adventures around the world. His latest? A trip through New Zealand.

Tom and Dave Bike
Tom (right) and Dave McCahill on the west coast of New Zealand in early March of 2020 just as the pandemic hit. They would cut their trip short (but not their riding!) and scurry home on Friday, March 20 to a changed world.

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