Built on the Trail, Inspired by Nova
TrailTales started with a simple idea: every hike has a story worth sharing — and technology should make that effortless.
How It All Started
Hi, I'm Cal Wilkes. I'm a storyteller, a hiker, and the creator of TrailTales.
I've always believed that the best stories are the ones lived outside — on ridgelines, in river valleys, under tree canopies that block out everything except the sound of your own footsteps. I grew up in Toronto, and while I've spent time building products and companies (including The Next 36 and founding Hotspot), the thing that keeps pulling me back is the same thing it's always been: getting outside and finding ways to share what I find there.
The spark for TrailTales came from my dog, Nova. She's the kind of trail companion who makes every outing an adventure — scrambling over rocks, nose-deep in every fern, always ten steps ahead on the path. After each hike I'd come home with a phone full of photos and a GPS track, and I'd think: "I should write this up before I forget it."
But I never did. Writing a blog post after a long hike felt like homework. Organizing photos, pulling stats from the GPX file, formatting everything nicely — it was too much friction. So the memories just sat in my camera roll, unseen and unshared.
One weekend I decided to fix that. I built a small tool that could take a GPX file and some photos, feed them to AI, and generate a polished hiking blog post automatically. The first post was about a rainy spring hike with Nova through the forest. It came out better than anything I would have written myself — complete with trail stats, an interactive map, and a narrative that actually captured what the day felt like.
That prototype became TrailTales.
Why We Built This
This isn't a business. TrailTales is a passion project, built because I believe the outdoors changes people — and that change deserves to be shared.
Think about the last time you discovered an incredible trail because someone else wrote about it. Maybe it was a blog post, a photo on social media, or a friend's story over coffee. That's what TrailTales is for — helping people share their outdoor experiences so others can discover new places to explore.
Most hikers aren't bloggers, and most blogging tools aren't built for hikers. There's this gap between having an amazing day on the trail and actually telling anyone about it. We want to close that gap. Upload your GPS data and photos, and TrailTales turns them into something beautiful — a real blog post with maps, elevation profiles, stats, and a narrative that captures what the day felt like.
Every trail tale someone publishes is a new window into a place someone else might never have found. A hidden waterfall in a provincial park. A ridge walk with views you can't believe. A dog-friendly loop that's perfect for a Sunday morning. When you share your hike, you help someone else find their next adventure.
There's a bigger picture here too. The most popular trailheads are overcrowded while incredible trails nearby sit empty. When more people share detailed accounts of the places they've been — real routes with real data — it helps spread people out across the landscape. It also gives hikers the confidence to progress further into the backcountry, because they can read firsthand accounts from someone who's been there before. Better information means better decisions on the trail.
That's why we built this. Not to make money — but to get more people outside, help them discover trails beyond the usual crowds, and make sure the stories from the trail don't stay stuck in a camera roll.
What We Believe
The principles that guide everything we build.
Every Hiker Has a Story
You don't need to be a writer or a content creator to share your adventures. We make it easy for anyone to turn a day on the trail into something they're proud to share.
The Trail Comes First
Technology should enhance the experience, not replace it. We handle the tedious parts — formatting, stats, maps — so you can focus on what matters: getting outside.
Sharing Inspires Action
When someone reads your trail tale, they might lace up their own boots. We're building a community where outdoor stories inspire more time outside.
A Note About Nova
None of this would exist without Nova — the four-legged trail partner who got me outside, kept me exploring, and gave me a reason to document every adventure. She's the original TrailTales user and the reason this project exists. Every feature we build, we ask: "Would this help someone share a day like the ones Nova and I have on the trail?"
Your Trail Has a Story Too
Join us and start sharing your outdoor adventures with the world.