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.

Tales from the AC: Our Generous Hosts

Discovery & Inspiration

American Challenge group biking through the desert in helmets during a summer of biking across the country

Completing the American Challenge — biking for six weeks and 3,000 miles across the United States — is a heroic accomplishment. It takes endurance, fortitude, and a whole lot of gumption.

What it doesn’t take is a whole lot of outdoor camping. Unlike other Overland trips, the American Challenge spends only one third of nights camping outside. Instead, families across the country open their homes, pools, or churches to a group of kids they’ve never met. After a long day of biking, a little air conditioning and a homemade meal can make even 100 miles seem worth it. And it’s this generosity of strangers that makes the American Challenge possible in the first place.

An American Challenge group poses in their high-visibility clothing while stopping in town on our teen biking trips
An American Challenge group stops in town

Sherry and Marion Whinrey have been hosting Overland groups for the past 20 years. That first summer, Sherry saw an unfamiliar group of kids biking to the park across from their house in Union, Mississippi. The Whinreys went out to investigate and learned, much to their surprise, that the kids would be sleeping there — in the park! Due to a miscommunication with the Chamber of Commerce, dinner wasn’t organized for these students as expected. Enter Sherry, who churned out a feast of sweet tea, popcorn, and PB&J’s. Twenty years later, she’s got hosting down to an art.

A group of teens posing with their hosts for the night in the bed of a truck after biking all day
Posing with our generous hosts

Melinda McLarnon got her first call from the Overland office 10 years ago. That first group took over her big house in Jackson, Georgia, spreading sleeping bags upstairs and downstairs. She cooked dinner and did everyone’s laundry. She says, “I absolutely fell in love with the kids.”

These families make hosting into a celebration and treat the bikers on their teen summer adventures like local celebrities. In Union, they’re escorted by the fire truck. Everyone turns out to watch “the bicycle kids.” The sheriff of Jackson greets the kids at the town line as they enter and exit, and then they’re treated to a free meal at Melinda’s restaurant.

American Challenge group wearing party hats before sharing a meal with their host.
An American Challenge group celebrates a birthday this summer

The kindness and generosity these families extend to kids who are not their own is genuinely moving. Year after year, they organize laundry and trips to the pool. They sponsor free dinners and set off fireworks. They pull out old newspapers featuring articles with Overland kids or photo albums of past visits, where students can recognize their sibling or a friend from school.

Nice gestures from our American Challenge hosts like this note left out to the bikers on our teen biking trips

When asked what inspires this generosity, Sherry talked about how it’s an opportunity for her town to rise to the occasion. And she loves to see students come back as leaders in later years. Melinda agreed: she has kids of her own, but she feels like these students are her kids, too.

If completing the American Challenge teaches you anything, it’s the importance of having an open heart. There are people across the country who upend their lives and empty their cupboards for a group of dusty bikers. It takes courage of all types to complete this journey, and the courage to be open and kind to others is just as integral to the American Challenge as that first glimpse of the Santa Monica Pier.

An American Challenge group poses together at sunrise to start of their teen biking trips
Getting ready to start a journey across the country

Editor’s Note: Every year, we have dozens of gracious hosts who help our American Challenge groups make it to the Santa Monica Pier. Some of them even write about the crazy groups of kids who decide to try to cross the entire country by bike. Read more about the different bike trips we offer here.

Teen Summer Adventures / Teen Biking Trips / Student Experiences

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