The hill seemed endless. It was the summer of 2006 and I was home from college, interning at this very magazine (dreams do come true!), and my then-boyfriend suggested we ride our bikes to his family’s house in Southwest Portland. Though we’d dated for a couple of years, I didn’t really understand where he lived—I was an east-side kid perpetually getting lost in the serpentine anti-grid of the west side. But on this balmy afternoon, I pedaled behind as he led us out of downtown and up the densely wooded curves of Terwilliger Boulevard. It was chill enough at first. But then it kept going. And going.

Sweaty and red-faced, I eventually made it up that hill. And though that relationship buckled, the bicycle and I stuck it out. When I moved back to Portland five years later, I claimed my mom’s aging hybrid and resolved to become a bike commuter, brandishing my helmet like a championship trophy. I loaded up my first set of panniers and learned to ride clipless, enduring several graceless topples in the process. On soggy days, I would swap steely looks of solidarity with other cyclists. On sunny days, I would sail past backed-up traffic, feeling sorry for (and, yes, slightly superior to) all those drivers in their metal boxes. And on weekends, I learned routes up and over Skyline Boulevard, along the Clackamas River, and into the Gorge.

Getting to know Portland from the saddle is how this city became more than just where I was from. It became the place I call home. It’s also, crucially, how I’ve maintained healthy doses of silliness as an adult, including not-at-all-awkward run-ins with coworkers on the World Naked Bike Ride. It’s that spirit that I sought to bring to this month’s urban biking feature, which is all about having more fun on two wheels. You’ll find tips for maximizing comfort and safety, several sweet summer rides (plus epic bikepacking trips in our Outdoors cover story, along with hiking and rafting), Pedalpalooza picks, and a slew of local cycling groups. I also dug deep into the city’s golden age of cycling—i.e., the 1890s—and found that Portland’s penchant for bike fun has deeper roots than you might expect.

I’ve climbed Terwilliger many times since 2006, including one spin with a few hundred others on the monthly Midnight Mystery Ride. That’s not to say my bike career has been uniformly glorious—ask me about the date that ended with two chipped teeth, a stitched-up chin, and a night in the emergency room. But this much I know is true: my favorite view of this city will always be the one from behind my handlebars.