Looking Back on 2025
This past weekend saw the first winter weather of the year here in Bozeman, Montana. The fall foliage mixed with fresh snow was an unignorable sign of the changing seasons, and as the office team begins to put away their trail running shoes and dust off their ski boots, I wanted to take the opportunity to reflect on Overland’s 2025 summer.
As ever, there’s no broad stroke that can be painted to describe the Overland summer: each group functions independently and builds their own special identity and experiences Overland in their own way. That’s a huge part of what makes the Overland model so wonderful. Yet, from where I sit, several themes rose to the surface and helped give shape to the shared experience of Overland this year.
Kids are as courageous and adventurous as ever, when given the opportunity.
The Overland team sees students and their families embark on a remarkable narrative arc every year, and in many instances, over the course of several years.
From our first conversations with families – when they’re trying to determine what trip is the best fit for their child – through the trip prep process, to the time out in the field, and then finally, to the feedback we receive at the end of the summer, we see a beginning, middle, and end of each student’s experience. In those storylines, the students who join us at Overland stand in direct opposition to the grumblings of “kids these days…”
- On one hand, yes, we recognize that it’s not easy to be a young person in the world today and that, yes, there are some concrete structures that are holding kids back from flourishing.
- But the students we get to know are resilient, energetic, passionate young people who jump at the opportunity to try new things, embrace discomfort, and make new friendships. Whether they are leaving home for the first time, or learning to backpack, or traveling abroad by themselves, or summiting Mount Kilimanjaro, Overland students impress and inspire at every level and every stage of life.
Does the Overland model help facilitate this adventurousness for our students? Absolutely. Small groups engaged in meaningful activities, away from technology, with great leadership provide a structure for students to be their best selves.
Take it from Miles, on Appalachian Trail Expedition, who shared, “My favorite part was being able to get off our phones and really talk face to face with other kids my age.” Even if it’s not always glamorous, it has resonance. The Caldwell family shared that their daughter “came home tired, joyful, brimming with stories, breathtaking photos, and, of course, a backpack of dirty, stinky laundry.” But, in the end, this is exactly the point; the Caldwell’s concluded that this was “all the things we’ve come to love about the Overland experience,” and we couldn’t agree more.
New dynamics and new opportunities.
For an organization in our 41st season, this summer brought a remarkable number of “firsts.”
Most notably, this was our first summer as an organization with offices in both Bozeman, Montana, and Williamstown, Massachusetts. For families, leaders, and students, the shift to a two-office model has had minimal impact (intentionally!), but it has been a necessary evolution for the year-round team, as we determine how to best support our leaders in time zones around the world and stay in close communication with one another. I feel so grateful to work in a role and among a community that is ever-improving and constantly tinkering with our product and our systems. The generative process allows us to home in on the core, non-negotiable features that make the Overland experience flourish.
That process of review and reinvention will carry forward into 2026.
We are excited to be launching two brand new hiking trips:
Additionally, we’ve revamped our service programs, taking them in a new direction toward environmental stewardship, and added an itinerary in our adopted home state:
Beyond just the trip offerings for 2026, we gathered as a year-round team this past September and had a broad-ranging brainstorming session about improvements and opportunities at Overland in 2026. Beth Larcom and I facilitated the discussion, and framed the session with “no bad ideas in a brainstorm.” In the course of an hour, every member of the team contributed a new idea, perspective, or area of focus for us to dig into together. We can’t wait to see those ideas come to fruition.
It’s the people.
Maybe it’s a cliche, but for an organization ostensibly focused on outdoor adventure travel, we find ourselves almost exclusively in the interpersonal relationship business. The places that we travel to, and the activities we embark on, are secondary and tertiary to the relationships developed in the course of an Overland experience.
One of our former leaders, Jake, distilled this sentiment nicely this year. He wrote that he sadly would not be able to lead again in a future summer as he enters the professional world, but he underscored the ways in which the Overland experience would remain relevant to him for years to come. He wrote:
Everyone I met– from the staff, to other leaders, and students– left an immeasurably positive imprint on who I am as a person now. I will never stop recommending a summer leading for Overland—it did more for me than any internship ever could.
For a leader who traveled across New England, the Colorado Rockies, and the Norwegian backcountry, Jake’s reflection resonated with the entire team. We see the same sentiment reflected in so many instances.
- Our leaders, as they share their highs and lows of their summer, always focus on the breakthrough moments of getting to know a student or seeing their group bond with one another.
- Families, when they share what went well for their child, always note the strong connections their child formed with other students and their leaders.
- And kids, who go into this experience preparing for a hiking trip in the outdoors, keep coming back because of the sense of community that they find at Overland.
For all of us, here in the Overland office, it’s takeaways like these that make us feel lucky to be in this line of work.
