The Day Nothing Went Wrong: A Surprisingly Thrilling Bike Adventure (And a Toast to Smooth Sailing)

Ever had one of those days where the adventure is... that nothing goes wrong? No flat tires, no surprise storms, no wrong turns (okay, maybe one wrong turn)? Join us on a ride where the biggest twist was the unexpected joy of a flawlessly smooth journey.

Ty on his gravel bike on the Rim Rock Trail

We haven't been able to ride our road bikes (or in Ty's case, his gravel bike) much in the last couple years, so our goal was a simple 20-mile out-and-back. We started by loading the bikes on the rack and driving down to Bend's Old Mill District. Parking alongside the Deschutes River put us in close proximity to oh-so-many of Bend's best post-ride celebration spots – a crucial detail for any adventure, if you ask me.

We jumped on the bike trail and headed towards Mount Bachelor. It was a nice steady grind, no crazy climbs but consistent. The blue sky was brilliant, temps were just right, and the trail wasn't remotely crowded. We cruised past gorgeous tall pines, grasses, and shrubs, reveling in the ability to ride quickly without the noise or danger of cars.

Reaching the Cascade Lakes Visitor Center, we noticed our bike path kind of... disappeared. A sign saying "Pavement ends in ¼ mile" pointed us in a different direction, under the highway. In a moment of foolish optimism (or maybe just sheer stubbornness), we ignored the sign and kept going. Surprise! The pavement did indeed end, and my skinny road tires were not happy about it.

Cycling along Cascade Lakes Highway toward Mt Bachelor

With a shared look of "I told you so" and a quick U-turn, we backtracked onto the highway, each silently blaming the other for not heeding that sign. The Cascade Lakes Highway was more of the same steady grind we'd been enjoying – nothing steep, just consistent climbing. The blue sky popped against the green of the trees and the red rock lining the roadway. As we neared our 10-mile turnaround point, one last big hill loomed.  We could have easily stopped short (and I may have considered it), but neither of us uttered a word about quitting.  We hit our goal, turned around, and whoosh – it was downhill all the way home! We took turns leading, drafting off each other, and having a blast hauling down the road. The sheer speed made our eyes water, and passing cars could barely keep up with us... okay, maybe I'm exaggerating a bit here. But it was pure magic!

Back at the Old Mill District, the promise of that post-ride celebration was calling. We found ourselves at Crosscut Warming Hut, drawn in by their cozy atmosphere, as well as their bourbon and local beer selection. A glass of Elijah Craig Small Batch was the perfect way to toast our smooth ride. The warm spice notes complemented the heat of our climb, while the subtle smokiness mirrored the fleeting scent of burning rubber from our downhill sprint.

Elijah Craig Small Batch and a Hazy IPA at Crosscut Warming Hut

Sometimes, the best adventures are the ones where everything goes right. And sometimes, the perfect bourbon is the one that mirrors the journey – smooth, unexpected, and undeniably satisfying.

Cheers to the unexpected adventures – both on and off the bike!

Michelle Eidam is a freelance writer with a thirst for adventure – exploring mountains, trails, breweries, and everything in between.