The outdoor industry is built on experience, and so is our team. Nearly 70% of the Flybook crew has worked as guides, outfitters, managers, or operators, spending years helping people connect with the outdoors through unforgettable adventures.
Those experiences have taken us across rivers, through mountain ranges, and into situations that taught us valuable lessons about leadership, preparation, problem-solving, and adventure itself. Today, those lessons continue to influence the way we support operators.
And while not everyone at Flybook comes from a professional background in outdoor recreation, a passion for adventure runs throughout the company. Every department is home to outdoor enthusiasts, recreationalists, weekend warriors, and newcomers eager to try something new. Whether it's hiking a local trail, paddling a river, learning a new outdoor skill, or planning the next big trip, our team genuinely enjoys spending time outside. We built Flybook to support this industry, and the people behind the platform are active participants in it.
In these posts, we're sharing stories, tips, and insights gathered from our own experiences in the outdoors. Some come from years of guiding and operating trips, while others come from personal adventures that sparked curiosity, challenged comfort zones, and deepened our appreciation for the places and experiences that make this industry so special.
Consider it trial-tested knowledge from the Flybook team.
Next stop: the Bitterroot Mountains along the Idaho-Montana border.
By Jake Cozart, Flybook Security Engineer
In August 2020, I biked the Route of the Hiawatha with my uncle, his wife, and a friend.
It was a clear day, but the ground was still wet from recent rain, which made parts of the trail a little slick.
The Route of the Hiawatha is located in the Bitterroot Mountains on the border between Idaho and Montana. It’s an old rail trail that’s now used for biking and hiking.
It is 15-miles of bike trail that runs along the old railroad, with 10 tunnels and several trestle bridges that give you some solid views of the surrounding forests and mountains.
One of the many tunnels along the Route of the Hiawatha.
Most people go in the summer or early fall since the trail is only open from late May through September, but August is a great time for it because the weather is usually clear and comfortable.
The trail itself is mostly downhill, which makes it manageable for most skill levels. There’s a shuttle at the bottom to take you back up if you don’t want to ride back.
The tunnels were a big part of the experience. The first one, St. Paul Pass Tunnel, was over a mile long and completely dark except for the light from our headlamps. Riding through it was a weird feeling - cold, damp, and almost disorienting. The ground in the tunnels was rough and wet in places, which made the ride more interesting, to say the least.
Coming out of the tunnels, we’d hit long stretches of trail that opened up to some pretty incredible views. The trestles were cool, too, giving a better sense of how high up we really were.
The trail itself was mostly downhill, so the ride wasn’t too tough, but it was definitely worth the trip.
Plan for around 2-3 hours, depending on how fast you ride and how often you stop to check out the views.
A few additional tips: definitely bring a headlamp or a good bike light for the tunnels, especially the first one, which is over a mile long and pitch black. Also, the trail can get slick in spots from recent rain, so keep an eye on your speed.
Overall, it’s a smooth ride with incredible scenery and just the right amount of adventure, especially with those tunnels and trestles. Make sure to reserve your shuttle and rental bikes ahead of time if you're not bringing your own.
No matter where the trail takes us, these adventures serve as a reminder of why we do this work: to help outfitters and adventurers focus on the moments that matter most. The outdoor community is where we come from, and it continues to shape and inspire everything we build at Flybook. We hope these stories fuel your next adventure, and maybe spark a few new ideas along the way.