Unridden™ is a trail-riding quest for people who like maps, bikes, and the dangerous notion: “I wonder if I could ride all of that.”

It started with a simple enough question: what would it be like to ride all of Phil’s Trails efficiently, maybe over two days, without repeating much? Many route-planning rabbit holes later, I had two big rides^[1], 80 miles of trail, and a new kind of motivation. Not faster. Not “win the internet.” Just two very solid days of fun.

That idea grew into another one: what if I tried to ride every trail in Bend in a season? Suddenly familiar zones felt new again. Weird connector trails had a reason to exist. The map became a checklist, a puzzle, and sometimes a personal problem.

That’s what Unridden is for. It gives riders a game-like challenge to explore their local trails, discover new routes, and find fresh reasons to get out the door. No podium required. No wattage sermon. No need to be the fastest dude/dudette in the parking lot.

Unridden is meant to be inclusive. Ride at your own pace, on the bike that works for you. Acoustic, e-bike, snack-paced, world cup wannabe, highly strategic, deeply unserious — it all counts. We'll even celebrate the slowest completions (Lanterne Rouge), because honestly, saving one tiny trail for the final day of the year is the kind of nonsense we respect.

Mostly, I hope Unridden helps make riding feel playful again. May it nudge you toward trails you forgot about, loops you wouldn’t have planned, empty snack wrappers, questionable route choices, and very good days on the bike.

So who’s behind Unridden? I’m Chris Bailey — a lifelong software developer who loves to ride, mostly off-road, ski, run, drink espresso, and build things.

I’ve worked at Adobe and other companies, and have been a co-founder at several startups, including HotelTonight, which was acquired by Airbnb. These days, my other primary endeavor is NatureQuant (check out our NatureDose app). I also have a fun weather app for helping plan rides and other adventures: Venture Weather.

I live with my family in Bend, Oregon, where I’m lucky to have trails, mountains, and good coffee close by. See you on the trails!

[1] Strava routes for: All Phils Day 1 and All Phils Day 2.