The Playfulness of the Trail

Finding Joy and Silliness in the Outdoors

There’s a certain reverence that comes with being in nature—walking beneath towering pines, listening to the quiet hush of snowfall, watching the light shift across a canyon wall. But alongside that deep awe, there’s also space for something equally important: playfulness. Too often, we think of the outdoors as a place for endurance, solitude, or quiet reflection. But what about joy? What about silliness?

I’ve found that some of the most memorable moments on the trail come not from the miles themselves but from the unexpected flashes of childlike delight. A few years ago, the Ice Age Trail Alliance had just updated its Monty the Mammoth mascot costume, and I was the lucky individual who purchased the older model at their benefit auction. I couldn’t resist putting it to good use: a friend was facing a hot, humid day training on the trails when suddenly, out of the trees, appeared a prehistoric beast cheering her on. The laughter and absurdity of the moment transformed what had been just another long trail run into something more memorable.

Or consider the group of trail runners who, every December, under the cover of darkness, sneak into the woods to decorate a lone tree along the trail. No one claims responsibility, and no one needs to. The magic is in the discovery—the way a tired runner rounding a bend might suddenly be met with dazzling ornaments and a few strands of tinsel, a small and quiet rebellion against the idea that adventure must always be serious.

And I’ll never forget that winter day, while trekking through fresh snow on a familiar trail, I stumbled upon a headless snowman resting at the base of a tree. Next to him, a plea was spelled out in sticks: "Help me find my head." I couldn’t help but laugh—and, of course, snap a photo. A quick glance upward revealed his missing head perched in the branches (how did they get that up there?), waiting to be reunited or simply to surprise the next passerby. That small act of creativity turned an ordinary run into something I still smile about today.

Play is not just for children. It’s an essential part of being human, a reminder that we’re allowed to take delight in the world around us. I know a runner who looks for - and always seems to find - heart-shaped rocks on her runs. I’ve heard of climbers who, reaching the summit of a grueling peak, don silly hats for their victory photo. I’ve watched kayakers navigate slow-moving rivers with plastic flamingos strapped to their boats, grinning at every passing paddler.

These small acts of whimsy do not detract from the grandeur of nature—they enhance it. They remind us that the outdoors is not just a proving ground for endurance, but a playground for the soul. They allow us to shed the weight of adulthood, if only for a moment, and to remember the sheer delight of being outside, untethered and unburdened.

And there’s something deeper to this idea of playfulness in nature—it fosters connection. When we engage in acts of joy and absurdity, we invite others to join in. A simple joke on the trail, a spontaneous game of rock-skipping by a river, or a shared moment of wonder over a particularly funny-shaped tree brings us closer to those around us. These moments dissolve barriers, reminding us that, at our core, we are all just humans finding our way through the wild together.

Even history holds examples of explorers and adventurers embracing a sense of humor in the wild. Antarctic explorer Ernest Shackleton, facing unimaginable hardships, encouraged his crew to engage in games, performances, and lighthearted camaraderie to maintain morale. Joy, even in small doses, has always been a necessary ingredient for endurance and survival in the outdoors.

At its heart, adventure should always leave space for surprise. When we take ourselves too seriously, we risk missing out on some of the magic of exploration. The most unexpected joys—whether it’s an impromptu snowball fight on a winter trek or dancing in the rain after a long hike—are often the ones we remember the most. They are reminders that the best adventures are not just about the destination but about how we embrace the journey.

The next time you set out on a trail, consider bringing a little mischief with you. Wear a ridiculous hat. Pack an unexpected surprise for a friend. Start a tradition that makes no sense but brings endless joy. The trails will always be there for quiet reflection—but they’ll also welcome a bit of laughter, too.

And who knows? Maybe one day, when you least expect it, you’ll round a bend and find something delightfully unexpected—a woolly mammoth, a twinkling tree, or even just the sound of someone laughing, carried on the wind.