In October of 2014, Overland Logistics Coordinator Conor Canaday scouted our Iceland Explorer trip. Recently, Tom Costley sat down to talk with him about his experience and the highlights of Iceland Explorer.

Tom Costley: Who should sign up for Iceland Explorer?

Conor Canaday: Active students who are excited to see one of the most beautiful and diverse places in the world should sign up for Iceland Explorer. Iceland is unlike any other place I’ve visited and offers a unique experience for adventurous students. Iceland Explorer is ideal for students who are interested in exploring the country on day hikes, a sea kayak trip and 6-day backpacking route through the island’s interior. It will give you the chance to experience one of the most up and coming tourist destinations in the world in a way that most visitors never see.

Conor hiking on Htrail

Conor hiking on Laugevegur Route

Tom Costley: What are three of the trip’s highlights?

Conor Canaday:
1. Exploring Iceland’s west coast alongside an extinct glacier-topped volcano, Snaefellsjokull
2. Paddling along the coast for an overnight expedition by sea kayak
3. Completing Iceland’s most renowned trekking route, the six-day Laugevegur Route

Tom Costley: What is the hiking like?

Conor Canaday: The hiking is moderately challenging; it is perfect for someone who wants to gain hiking experience in a dramatic and unique landscape, but is also appropriate as an introduction to backpacking. Our itinerary starts with day hikes along one of the rugged western peninsulas, where we’ll stretch out our legs and get used to hiking, but also take breaks to enjoy the views along the trail. Due to its proximity to the ocean, the hiking is low elevation (you will not exceed 4,000 feet) and allows the group to experience both the glaciers and coasts of Iceland.

After gearing up for our backcountry hike, we’ll head out on the truly world-class Laugavegur Route. The Laugavegur gives our groups the chance to see and experience Iceland’s wild interior while still remaining on established trails. This trek offers changing scenery every day—from the vibrantly colored hills of Landmannalaugaur at its start to the steaming volcanic vents of Fimmvorduhals Pass and finally the thundering cascades of Skogafoss at its finish. Although it will be a challenge, it is also a great beginners backpacking trip.


One of the many beautiful and unique landscapes on Iceland Explorer

Tom Costley: Why is Iceland called “The Land of Fire and Ice”?

Conor Canaday: Locals and tourists call Iceland the Land of Fire and Ice because it offers both extremes; many parts of the island are covered by extinct volcanos topped with glaciers and ice fields, including Vatnajökull, one of Europe’s largest glaciers. We will spend our time hiking in the dramatic valleys created by these geologic phenomenon over the centuries. Although Iceland has notoriously variable weather, it’s not as cold as the name may suggest. Even though the island is just south of the Arctic Circle the ocean current from the south makes the climate temperate with average summertime temperatures in the 50s (and highs up to the 70s).

Tom Costley: What was the highlight of your scouting trip?

Conor Canaday: Honestly it was the variety that each day brought while visiting Iceland. I was constantly surprised by how extraordinary many of the views were around the island. It is a location unlike any other on earth with such big contrasts between the mountains and ocean, the glaciers and towns and views of volcanoes on the horizon. The beautiful rural areas and friendly locals also made me excited to get out and explore each day.

Conor checking out a hot spot

Conor checking out a local hot spot

Why I Return by Luke Knisley

A six-time Overlander, Luke Knisley started going on trips during the summer after his 7th grade year. First, Luke went on Cape Cod & the Islands; then he biked Vermont; next, he biked the New England Coast; then he headed west to bike Pacific Coast and California; and finally in 2014, he biked from Paris to the Sea. In the following essay, Luke reveals why he returns to Overland each summer.

Nice, France. Burlington, Vermont. Acadia National Park. The California Redwoods. These are just a few of the places I have visited on Overland bike trips. Without Overland, I wouldn’t have been to any of these places. The varying geography isn’t the only reason why I long to return each summer to an Overland biking adventure.

I keep returning because I love the structure of the trips. On these trips, I feel like I’m on a team of leaders. I love being able to have a say in what we do as a group; especially when that group has a shared goal it desires to achieve. One of the ways that I feel like an equal leader in the group is through crews. Everybody in Overland’s small groups rotates through four crews: journal crew, clean crew, cook crew, and special operations, or spec-ops. I particularly enjoy being on cook crew and spec-ops. I feel like I have the most influence on cook crew, because we are directly responsible for not only planning the meal, but also for the grocery shopping and cooking. On cook crew, our ability to make decisions and change our plans on the fly keeps the group moving. I also like being on spec-ops because we are really the catch-all for the group. Whenever somebody in the group needs help, spec-ops steps up. We do everything from filling water bottles to maintaining bikes.

Another reason why I keep returning to Overland is the clean environment that gets promoted. By clean environment, I am not referring to the actual physical environment, but rather to the verbal and mental one. One of Overland’s core values is respect. On Overland, we respect each other, we respect the people around us, and we respect the environment. Swearing, drugs, and alcohol are prohibited on Overland. The leaders encourage us to keep things Overland-appropriate, or “O-pro”. They remind us, if the conversation strays, to keep it in the “O-zone”. Exclusive relationships are also strongly discouraged on Overland. They don’t allow more than two pairs of friends in any one group in order to help maintain geographic diversity. Thanks to Overland, I have friends all over the country and the world.

I also keep coming back because every trip is a learning experience for me. On Overland, I’m always learning about new cultures, places, and environments. This past summer, I biked through France with Overland. Thanks to Overland, I got to learn a lot more about French culture as a whole, and about how much it differs based on where you are in the country. For example, Paris is very different from Nice, even though they are only a few hundred miles apart.

Another thing that keeps bringing me back to Overland is the opportunity to unplug while I am on them. We aren’t allowed to bring any personal electronics, not even an e-reader, so the only source of news is through the leaders or the occasional newspaper. Before my first trip, I didn’t know what it would be like to be out of touch for an extended period of time, but I came back with no regrets. I’ve discovered that it’s nice to be able to escape the world for a while and to live in the moment for a time, something I find harder to do with each passing year.

“Once you have tasted flight, you will forever walk the earth with your eyes turned skyward, for there you have been, and there you will always long to return.” I found this Leonardo da Vinci quote in the book of poems and quotations that Overland gives to its students every year, and it has stuck with me ever since. This quote truly describes how I feel about Overland, thanks to the leadership and learning opportunities and clean environment that their trips present.


Royals Magic by Max Londberg

Last night I was at the World Series. The night before that I was also at the World Series. A week ago, when the Series started with the first two games at Kauffman Stadium, I was lucky enough to be there, too. Biking into the stadium for my first World Series game, and each successive one, I saw more jubilant fans and media vans than I thought one parking lot could reasonably contain.

When I first started working at Kauffman, about 10 days after Overland’s leader closing in August, I didn’t know much about the Royals. I did know, however, that they were hiring photographers to take photos of fans. I also knew that I was jobless. Putting two and two together, I applied, got hired, and thought it would be a fun job until the end of the season, when the Royals would inevitably miss the playoffs. I mean, these were the Kansas City Royals, I thought then.

But I was wrong. A little more than two months later, I found myself bemused by good fortune as I walked past hordes of blue-bedecked and buzzing fans to enter the World Series in a stadium and city that had waited 29 long years to get back to that stage.

And I was there, and I couldn’t really believe it.

Life is about perseverance and hard work and all that, but I tell you, there’s an unmistakable amount of pure, unbiased chance in all of it.

Before the Series, you can perhaps imagine the thrill I felt with each Royals postseason win, as each one made a World Series berth more plausible. The only time I doubted was in that wild card game against the Oakland A’s. The Royals had to claw back from a four-run deficit, which they did using a combination of gutsy base stealing and sacrificial bunting. It was selfless, fundamental baseball at its best. And in the 12th inning, Salvador Perez—the team’s bearish catcher—came to the plate for the biggest at-bat of his career. Two outs, man on second, chance to send his team to the divisional series—storybook material. And Perez delivered, pulling a ball down the third-base line that just—just—zoomed past the third baseman’s outstretched glove. The ball couldn’t have been more than an inch from the leather.

The next two series saw the Royals sweep both the Angels and the Orioles. During the fourth and clinching game against the Orioles, with the Royals nearly a lock for that long-awaited World Series berth, the buzz in the stadium was palpable. In the top of the ninth, as the Orioles hopes were expiring, I stood 20 rows from the field on the first base side. My view of the diamond was somewhat obstructed by the mass of blue, but I enjoyed watching the fans almost as much as the game. As the final out neared, I watched nearly every fan raise a phone to record the moment. When the final out gloriously came, fans high-fived like they normally do after any big moment, except that this session of high-fiving lasted far longer than any other I’d ever seen. And the roar was otherworldly.

The Royals were headed to the World Series.

In the first few games of the Series, I noticed that adults were kids again. Many of them told me how they’d been at the Series back in ’85. They said they’d watched the game with parents who were now gone. Others were the parents who were now the grandparents with little ones in tow yet sharing the same exuberant energy as their grandchildren.

Another thing I noticed was how such a simple thing as a game of baseball can unite an entire city. When I wasn’t at Kauffman, I still saw Royals pride everywhere: in logos painted in restaurant windows, “We Believe” on billboards and the sides of commercial vehicles, and in so many fountains dyed Royal blue. Some of the downtown buildings even beamed blue lights onto their roofs, giving them the appearance of glowing blue crowns atop the city’s towers. All the buses, which are paradoxically ubiquitous and impossible to catch because of the city’s pervasive construction, flashed “Go Royals!” in their destination displays.

After game two of the Series, with the games shifting to San Francisco, I found myself having conversations with strangers about the team every time I left my house.

“I hope they win,” I’d always say. And I would mean it. I genuinely wanted the Kansas City Royals to win. The positivity surrounding them, the underdog attitude, the joy throughout Kansas City made not rooting for them impossible.

When I told people, “I hope they win,” they always and without exception would declare, “I know they’re going to win. I know it. It’s not about hope. I know it.”

This unwavering conviction was a result, I think, of years of waiting. People thought it was simply the Royals’ turn to take the crown. Not only was the team respected outside of Kansas City, but they seemed to be so Cinderella-like, what with their gloomy past and meteoric rise to relevancy, that imagining them failing was, well, unimaginable. When game seven rolled around, I gave up my petty hoping and started believing, really believing, that the Royals would win it all.

But, alas, sport is too unpredictable for belief.

Salvador Perez, he of Wild Card heroism, had another crack at glory when he stepped to the plate in the bottom of the ninth inning. Two outs, man on third, chance to send the final game of the World Series to extra innings—storybook material.

But he skied one into the night, high above the ‘ohh-ing’ crowd. For a second I thought the ball might drift foul, but the third baseman had plenty of room and corralled it, ending the wild ride with sudden and wrenching finality.

Even as the Giants celebrated on their stadium’s diamond, Royals fans started chanting, “Let’s go Royals.” But not in the roaring way characteristic of a Royals rally, and not even in a mocking or angry way that I’d honestly expected coming from fans that had waited so long and come so close. No, the chanting was done in a thankful, empathetic way. The fans were sharing in each other’s hardship—one that started 29 years ago and will continue into next year. The gesture, I thought, was nearly as beautiful as would have been even the sweetest victory celebration. It showed pride, loyalty and a willingness to keep waiting. Royals fans could have turned angry, even ugly, but they didn’t. As the blue-bedecked mass flooded the exits, “Let’s go Royals,” morphed into, “Thank you Royals.”

Their gratitude was as unexpected as it was beautiful. And for the first time in my life, I found myself thinking fondly about baseball’s next season.

Max Londberg led Overland’s Summer Writing Program this year. Afterward, he moved to Kansas City. Since then he’s written a lot, including a novel that’s nearly finished. If you work in the publishing industry, Max would love to hear from you.


OUTSIDE magazine chooses Best Places to Work 2014: Overland makes the list

Overland has been selected as an OUTSIDE Best Place to Work 2014. Each year, OUTSIDE recognizes the top 100 companies in the United States that help their employees strike the ideal balance between work and play. These companies encourage employees to lead an active lifestyle, are eco-conscious and prioritize giving back to the community. The entire list of winners appears online at Last year, Overland made OUTSIDE’s Best Places to Work 2013.


The A-ha Moment by Andy Pass

A three-time Overlander Andy Pass wrote an essay about his 2014 American Challenge trip. Before riding cross-country,  Andy went on Nova Scotia & Acadia in 2012 and the Pacific Coast in 2013.

It was 11 am, and it was already 105 degrees in the Mojave Desert. We had been cycling since 6 am and had two more hours to go. The conditions were tougher than any we had seen. But I wasn’t thinking of quitting. Not with only two days left. Not after five and a half weeks and 3,100 miles already behind me. I was thinking about seeing my family and friends. I could picture them yelling at the top of their lungs to welcome us at Santa Monica Pier. I was also thinking about what an incredible trip I was about to complete, and how much it meant to me to be reaching a goal that I had set for myself so many months ago.

This was my third summer participating in bicycle trips around America and Canada. I rode over 3,000 miles in six weeks. My trip this year started in Charleston, South Carolina, and ended in California. I enjoyed seeing the country from the seat of a two-wheeled vehicle. On the trips, our group of 12 kids from different parts of the country starts bonding as soon as we see each other in the baggage claim and remains close until the last day when tears and hugs are shared.

With the exception of thunder and lightning, we biked in any weather, all day long. The pace was demanding, averaging 80 miles a day. The rain was our shower – and when we didn’t feel a drop for weeks, we biked even faster to block out the stench.

Since this was a family away from home, we experienced high and low moments throughout the trip. The low moments were somehow the best of all, because that’s when we learned to solve problems together. When we had a bad day, we became even closer, cheering and helping each other through the tough times. I learned to put the group before myself and gained immeasurable confidence and utter determination to push through most any challenge. Some days were really tough, and if we hadn’t all learned to work as a team we wouldn’t have made it.

There were many incredible moments, too. We took in the world around us from a point of view that only bike riders can experience. On the descent from Wolf Creek Pass in Colorado, we admired the amazing blue sky, fluffy clouds and plentiful trees in the background. My jaw dropped as we rode down. It felt like a dream. Journeying down the elevation with people I love was a perfect experience that led us to this high point of the trip.

I do these trips to find the “A-ha” moment. I love the sense of accomplishment when I see the summit of a hill, after hating the anticipation of climbing it. It can take me two hours of cycling straight uphill to reach the top. Many members of my group had breakdowns as we struggled to continue peddling. As much as I hate a climb, there is no better feeling than seeing the mountain peak looming closer in my sight.

Every day I needed different amounts of mental strength. Sometimes, something as small as a letter from a family member was all I needed to stay motivated. Other times the motivation came from me. When I became fatigued, I focused on keeping my goals, large or small, in mind. I learned that I can set a goal and complete it, even if it is as challenging as riding my bike through the Mojave Desert.

Andy celebrating with his leaders Jackson and Annika in the Pacific Ocean

Andy with his leaders Jackson and Annika

Apply Now for 2015 Summer


Thank you for a terrific 2014 summer!

After a fun-filled break during which Overland year-round staff traveled to Switzerland, Norway, Iceland, Maine, Michigan, Colorado and California, we are back in the office and are busy planning our trips for 2015. Please give us a call at 413.458.9672 with any questions. If you’re ready to apply, simply fill out our online application.

Enrollment Update from Director Tom Costley: Thursday, May 8, 2014

We still have spots left for girls and boys on a number of trips. Please take a look at availability below:

  • Is your 8th-11th grade son interested in cultural engagement, outdoor exploration and service? Consider Field Studies Costa Rica (Sunday, June 22 to Friday, July 11 for 8th-10th grade boys); Field Studies Peru (Friday, June 27 to Friday, July 25 for 9th & 10th grade boys) and Field Studies Thailand (Thursday, June 26 to Friday, July 25 for 9th-11th grade boys)
  • Do you have a daughter in 7th-10th grade who is interested in developing her leadership skills while exploring the Maine Coast or the Yukon Territory? Check out Maine Coast Leadership (Sunday, June 22 to Friday, July 4 for your 7th, 8th or 9th grade daughter) and Yukon Leadership (Sunday, June 22 to Friday, July 11 for your 8th, 9th or 10th grade daughter)

Please give us a call at 413.458.9672 with any questions. If you’re ready to apply, simply fill out our online application.