Imagine a man, let's call him Jerry Shrall, who decided to embark on an extraordinary journey through the streets of Portland. And what a journey it was! Jerry, an engineer with a passion for cycling, set out to explore every single bikeable street within the city limits. He pedaled across the Ross Island Bridge, both ways, and even ventured into areas he never knew existed.
Jerry's cycling adventure began as a practical commute from Southeast Portland to his office in Beaverton, a distance of roughly 16 miles. But little did he know, this daily routine would turn into an epic quest. Using the Wandrer website, he tracked his travels and realized in April 2025 that he had already covered a significant portion - about 30% - of Portland's bikable streets.
Wandrer, a clever app linked to sports tracking apps like Strava and Ride with GPS, offers a unique perspective on your travels. It gamifies the experience, showing you the percentage of an area you've completed, be it your neighborhood or the entire world. And it was on this app that Jerry discovered he was at the top of the bike leaderboard for Portland, having conquered all 2,400 miles of bikeable streets, with several others hot on his trail.
By November, Jerry had completed most of the city, changing his route to work to cover as much ground as possible. All that remained was a tiny fraction - about a third of a mile - at Portland International Raceway, which was only accessible on and off. With the help of his wife, he finished this section on November 30th, during the track's 'Winter Wonderland's Bike the Lights Night' event.
Jerry's journey not only took him to familiar places but also introduced him to hidden gems. He discovered Mount Tabor, a favorite biking spot close to his home, and Pittock Mansion, which he had only visited once before.
"I'm kind of shocked at how many places I didn't know in Portland," Jerry shared while standing on Mount Tabor.
Among his other favorite riding spots are Rocky and Powell buttes and Northeast Sacramento Street above the Rose City Golf Course. But it wasn't just the breathtaking views that made his journey memorable. Jerry encountered many dead ends, some of which were frustrating, especially the steep, gravel-filled ones in Southwest Portland. However, he also found hidden treasures like George Himes Park, a little-known spot with a perfect bench where he could recharge and watch people racing boats on the river.
Now that Jerry has completed Portland, he's setting his sights on new challenges. He's determined to explore Clackamas and Washington counties, aiming to cover as much ground as possible during reasonable commutes or long weekend rides. And when he's done with that, there's always the Oregon leaderboard, where he currently ranks second, having covered about 2.5% of the state's 194,000 miles of bikeable streets.
So, what do you think? Is Jerry's journey an inspiring tale of exploration and discovery, or just a quirky obsession? Feel free to share your thoughts in the comments below!
