Saturday’s ‘Cutty Cap Challenge’ offers prizes and an excuse to explore

Riding bikes is fun. But if you ride a lot, it’s easy to get stuck in a rut. Sometimes you need something — like a goal or a game — to awaken your cycling spirit. For Portland-based Ride With GPS, the Cutty Cap Challenge is exactly that.

Now in its fifth year, the event has been reimagined as a live-action game that will be played by adventure seekers in 55 cities across the globe. It started in 2021 as a relatively traditional scavenger hunt. Ride With GPS (RWGPS), a company known for its popular route sharing and route making app, hid cycling caps in random locations and encouraged customers to go find them. The next year they added prizes, then expanded it to cities beyond Portland, and now it’s become a hotly anticipated start to the summer riding season.

“Cutty” is a term used to describe a route that’s a bit hidden or off the beaten path. Think of a cool spot you ride that isn’t well known, or that is borderline trespassing or sketchy for some reason. That’s cutty. There are a lot of beloved cutty routes in Portland, and this scavenger hunt is meant to encourage more folks to use them.

RWGPS Marketing Director and creator of the Challenge, Kevin Prentice, says the goal is, “To get people out riding in their city, and hopefully to a location or multiple locations they have never ridden. A new park, a new viewpoint, new trail, new business, solo or with friends, and have fun doing it.”

The challenge kicks off at 8:00 am sharp local time in 55 different cities around the world — from Sydney to Santiago, Osaka to Oslo. That’s when the location of at least 10 custom designed cycling caps will go live (additional cap locations will be announced after the first batch goes live). The locations are revealed in the RWGPS mobile app and participants compete by seeing who can find the most caps and bandanas (with a very cool design by artist and bike adventurer, Chas Christiansen aka @notchas on Instagram). Points accrue with each cap located. If you find it first, it’s yours and you get the bragging rights. But you can also score if it’s already been claimed. Players get bonus points by uploading photos and completing various missions that are broadcast throughout the day.

For Portland players, RWGPS has set up special prize giveaways with The Athletic. But to win them, you’ll need to unravel the hiding skills of Ron Lewis, one of the guys behind riding group Our Mother The Mountain, who Prentice describes as, “the unequivocal leader when it comes to both cutty locations and their descriptions.” “His locations will be off the beaten path, sometimes hidden in a drain pipe, not just a tree but a particular tree branch that resembles something, or maybe the cap is in a somewhat popular spot but his clues to find them are often riddles that also include song lyrics. Plus, nobody knows the city and it’s cutty locations better than he does.”

So if you like a good bike scavenger hunt and want a really fun excuse to explore the city — all while competing against other riders for points in a real-time digital game — download the app and check out the Cutty Cap Challenge website for more information.