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.

Take Time to Get Outside

Independence & Self-Reliance

Campers can't help but throw up their hands this summer when hiking on the Appalachian trail challenge program

Last week, those of us in our Williamstown office made the adjustment to… not being in the office. On Monday, we took our desktops, our keyboards, our notebooks, our pens, and even our chairs home with us to begin our new phase of remote work. We set up new stations on kitchen tables or in bedrooms, practiced using Zoom (we still haven’t gotten the hang of remembering to un-mute ourselves when we want to talk), and prepared to adjust to life working in a very different kind of way. For an office that is collaborative and warm, where we all come in every day excited to be working with people who are colleagues as well as friends, the transition to isolated work was one that was necessary, but a little daunting.

For all of our Overland families, the last week has been a blur. News updates come in fast—it’s easier to be connected to the digital world than ever before—and with them come notes from friends and family: “Did you see? Have you heard?” Kids and parents are at home together, likely for the first time since the winter holidays. But this time they’re trying to listen to online lectures, take work calls, and keep up with friends and colleagues while under the same roof. WiFi networks are stretched thin. Every day brings new changes and new ways we have to adapt.

As we in Williamstown adjusted last week to our new, virtual office, we began that process of adaptation. Many of us were used to walking to work; now, we take a walk before work around our homes. We were used to making extra-strong pots of coffee in the office kitchen; now, we make single cups. We normally meet on Friday mornings at Tunnel City, our local coffee shop, for Coffee Break: a shared breakfast where we catch up, talk about our weeks, and spend some time together before starting the work day. Last Friday, we held Coffee Break on Zoom. Our new routines are different, but they have the feel of something familiar. They’re new, but comforting.

Overland shares coffee while they plan teen adventure travel
Overland Staff at Coffee Break on Zoom last week

It’s hard to find many routines that haven’t been changed by our new limitations. A stop at your local coffee shop might not be possible, your walk to work no longer necessary, or your after-school sport no longer practicing. But finding the routines that can stay the same can offer some structure and stability.

Those of us who work at Overland love getting outdoors—it’s at the center of what we want for all of our students, and what we work for all year. During these times of social distancing, we’re lucky in that many of our outdoor routines don’t have to change all that much to continue as they always have. Not only does getting outdoors mean a welcome return to the familiar, but it’s been proven to make people happier and healthier.

Last week and this weekend, we asked some of our staff members to share how they’re making time to get outside. They’ve offered a few suggestions for us here:

Go For a Walk

A closeup image of two pink and white flowers in full bloom
Flowers in Washington, DC

For Lauren Earls, who works on our Admissions team remotely from Washington, DC, this weekend was the perfect time to get out for a walk: “This weekend included lots of outdoor time on long walks and in my backyard in an effort to take full advantage of the beautiful spring weather. Flowers are in full-bloom and lots of wet weather means that everything is lush and green. For me, it was important to get outside after a busy work-week and to remind myself of the beauty and promise of our currently unpredictable world.” 

Brenda Briguglio, who also works in Admissions, noted something similar: “This weekend while out on one of my two daily walks I was grateful for the silence. Listening to the river flowing over rocks, the birds singing and the wind as it moved the leafless tree branches, I was reminded that the earth is driven by its own rhythm and always in motion.  Aligning ourselves with nature means aligning ourselves with that same rhythm and motion. Get outside if you can and listen.”

Closeup of a woman's face, wearing a warm hat, with a herd of cows grazing in the background
Laura out for a walk with some cows

Laura Schoenbaum also went on a walk outside of town: “Hopper Road is one of my favorite walks when I don’t feel like planning. I park my car at the base and walk 2 miles up to the top. It gets progressively more beautiful as you go higher. The road eventually turns to dirt, then ends at a spectacular meadow and Haley’s Farm, where you can admire the peaceful cows and their spring calves. Then you can continue up into the Hopper on the Mount Greylock trails, or turn around and head back down.”

… And Bring Your Dog, Too

A friendly beagle standing on a hiking trail surrounded by trees and leaves looking at the camera.
Tug gets out on a walk with his loving owner

Chris McAlister went for a walk, but brought her dog, Tug, along with her. “There are a few things that have been comforting during this time. The first is having my immediate family healthy and safe in our home. While it’s crazy and a new normal (with no school), the opportunity this has given for us to slow down and be present with one another has been amazing.  Second, is our ability to connect socially via the internet. Zooming with my whole family or my college roommates or my exercise buddies has given me the chance to connect in ways that we didn’t always think about.  This has opened up a whole new world.  Lastly, my sweet, Tug.  Regardless of the fact that he can’t get sick from me or other dogs, he remains my constant companion and my stress reliever.  He’ll walk as many steps as I am willing to…every single day.  He gets me outside and keeps me sane.”

Get Out on a Run

A man and woman crouch next to some flowers and a pine tree, smiling at the camera.
Ben and Meg stop to smell the flowers

Trip Planner Ben Grannis picked up the pace for an after-work run this week: “Working from home for the first full week ever made me realize how important getting outside is for mental health and clarity. Spending so many hours in the same building makes the feeling of getting outside and feeling the fresh almost-spring air so much sweeter. I chose to run off some of the built-up energy I collected this week by going up a big hill overlooking Williamstown with a much more veteran runner and fellow Trip Planner Meg Pritchard. Along the way, Meg and I found a patch of crocuses (see photo!), and we REALLY felt spring is near.”

Conor on his run

Conor O’Brian also got out for a run: “I feel fortunate to live in a place where the outdoors are so accessible, and I took advantage of this beautiful (albeit, chilly) weekend with a run on Saturday and a bike ride on Sunday. Staying physically active outside has always been my outlet – my reset button. A run or a bike ride through a place you know so well can be an opportunity to see the world from a different perspective, a different pace. It’s a reminder that the world is far larger than just what’s going on in one’s life. This seemingly constant rediscovery of perspective is what keeps me coming back!”

Practice Outdoor Yoga

A yoga mat, laptop, and water bottle sit on a stone patio surrounded by gravel. In the background are rolling hills and pine trees, and the sky is cloudy.
Yoga at the Clark

Sara Levine, who works on our Admissions team, took some time this weekend to get outside while doing yoga: “Over the past few weeks, I’ve been trying to stay connected with my loved ones via Zoom and Facetime since I live hours away from my family and friends. I’ve been very cognizant of my screen time lately and have been focusing on stepping away from technology every day to spend time outdoors. The Clark Museum in Williamstown has become my safe haven. I’ve spent many afternoons in the fields doing yoga, taking Zumba classes led by my friends, and exploring the trails that surround the museum.”

Go For a Ride

A man wearing a winter hat winks at the camera while biting into a banana. Behind him, his bike rests on a simple wooden fence. A beach and the ocean horizon in the background.
Matt stops for a snack break

Trip Planner Matt Duncan went for a bike ride in his hometown in New Jersey. “Here’s a picture from my bike ride down to the beach this weekend! It’s almost exactly 50 miles from my front door to the beach (when taking less trafficked back roads) and I have always wanted to make my first century day in the saddle there and back. Like most people, I am trying to come to grips with our new reality, and I found my mind continually drifting towards all the amazing memories I have had with Overland in past summers. Staying optimistic and daydreaming about trip start at Cole Field kept my legs pumping all day long. I cannot wait to have groups of kids getting out and exploring the world together this summer!”

A blue tarp and straps of webbing sewn together to create a small pack. Scissors, needle, thread, and a sewing machine can also be seen.
Quinn’s DIY frame pack

Quinn Mendelson, who also works in Trip Planning, went for a bike ride as well… but his was with newly-crafted gear: “I’ve been riding my bike – a lot! We’re in that time between winter and spring where the weather isn’t always on your side so there’s a good degree of creativity involved with layering and how to store all that on your bike as you warm up. Over the weekend I spent a few hours with a sewing machine and made a frame pack to hold some of my stuff. An old tarp, an overland T-shirt to line the inside, and some Velcro I found is all it cost me (and I think it looks kind of cool!).”

Anya Parauda, from our Admissions team, went for a ride with Quinn as well: “This weekend consisted of a quick bike ride about beautiful Williamstown with my colleague Quinn and a hike up Pine Cobble. While on the ride, we stopped by a local farm stand to pick up some cheese (supporting local farms, but keeping our distance from others) and pet some newborn calves. What a great reminder that nature will continue, calves will still be born as cute as ever, and flowers will still bloom. Getting outside is one of the few constants for me in these uncertain times and continues to bring a sense of peace.”

Take a Hike

A man walking away from the camera on a wooded trail covered in dead leaves towards a sunny clearing.
Finishing up the hike during golden hour

Trip Planner Meg Pritchard took time to get out and hike this weekend: “All week I had felt pretty cooped up in my house. Daily walks and runs are great, but I still felt really connected to what was going on in the news. When Ben Grannis, another Trip Planner, suggested going for a hike up Stoney Ledge, I jumped at the chance. It was an amazing couple of hours—for just a little bit of time, I was focused totally and completely on being here now, and appreciating the beautiful ridge we hiked on. It was a perfect afternoon!”

Go Backcountry Skiing

A snow covered hill with two prominent pine trees overlooks a sparsely forested mountain valley. A cloudy sky obscures distant mountain peaks.
Sarah’s view

Resorts may be closed for the time being, but Trip Planner Sarah Kravitz used her time to get outside and ski: “This morning I went on a little backcountry ski adventure to Circle Awl Peak in Big Cottonwood Canyon, UT. In a time of so much uncertainty and worry, I find comfort in physical challenge the beauty of the great outdoors. For a full 2.5 hours I didn’t think once about Covid-19 – I was fully immersed in the here and now. I listened to the rhythmic click-clack of my skis with each step I took on the way up and felt pure joy with each turn I took on the way down. We had done some research, set a goal to complete that route and went out and did it. That sense of accomplishment feels so good every time and also reminds me how lucky I am to be able to use my body to center myself.”

Just Get Out!

Whatever you do and wherever you are, we encourage you to take time for yourself and get outside today. In difficult and uncertain times, the peace and energy we find in nature can make a tough day just a little more approachable. As we get outside, know that we are thinking of you all, and sending best wishes to you and your families.

Filed Under: Teen Adventure Travel / Teen Summer Adventures / Teen Summer Biking Trips / Teen Summer Hiking Trips

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