2025 Ride With GPS Cutty Cap Challenge

The fifth-annual global bike scavenger hunt kicks off Saturday, May 31 in 55 cities worldwide. Find out how you can join the hunt below…

Cutty Cap Challenge 5.0

The 2025 Cutty Cap Challenge presented by Ride With GPS is set to transform the cycling community's beloved scavenger hunt into an exciting live-action competition celebrating its fifth anniversary. San Diego joins the global event thanks to a partnership with Ride With GPS, with the hunt scheduled for Saturday, May 31st. Participants can stay updated on key details and additional news by subscribing to the Gravelstoke newsletter here.

This year's completely reimagined challenge allows cap seekers to earn points in real-time by visiting multiple locations and documenting their adventures with photos. The competition spans both global and local levels, creating opportunities for cyclists to compete against riders worldwide while also vying for recognition within their own cities. The accessibility of the challenge remains a key feature, as anyone in participating cities can join the hunt using only the Ride with GPS mobile app, which serves as the central platform for all activities.

The anniversary celebration brings together more cities, surprises, and opportunities than ever before, all centered around winning custom caps designed by artist and bike adventurer Chas Christiansen. The prize structure offers multiple ways to win, starting with The Cutty Crusher grand prize for the highest global point scorer, who receives the ultimate prize package and year-long bragging rights. Local competition is recognized through The Local Legend category, where the top scorer in each city wins a limited-edition five-year bandana, custom Ride with GPS water bottle, and free annual Premium subscription.

NEW MERCH!

26oz Purist Bottle

22oz Purist Bottle

Gravelstoke Glitch Tee

Gravelstoke Reroute Tee

EPIC Sticker Pack

The original honor remains The Cap Master designation, earned by physically finding and claiming one of the hundreds of Cutty Caps hidden throughout participating cities. With 55 local partners hiding at least 10 caps per city, the physical hunt maintains its traditional excitement. Additionally, The Cutty Cruiser category offers randomly awarded bonus prizes based on point accumulation, with each point serving as an entry into the drawing.

The hunting process requires downloading the Ride with GPS mobile app, which displays cap locations once they go live and provides bike-friendly navigation directly to each spot. This integration ensures participants can seamlessly move between digital point collection and physical cap hunting, making the challenge accessible to friends, families, riding buddies, and neighbors who want to participate in this global cycling celebration.

Participating Cities

NewsDave MalwitzMay 24, 2025ride with gps, cutty cap challenge, scavenger hunt