As a passionate cyclist who has spent the better part of 30 years calling Bend home, I’ve had my fair share of exposure to different riding options in Central Oregon. But to call out my favorites is honestly much more of a challenge than I initially expected when the Tour des Chutes asked me to come up with a list of my favorite rides in the region.

For road rides, however, it’s not hard at all. There are three that stand out to me pretty clearly above the rest. Most of what Bend has to offer for road riding, when compared to so many of the other places I’ve been fortunate enough to ride over the past few years, is far too vanilla for my taste. Yet when I’m away for long enough, even riding some mind blowing climbs on the Front Range or descending a winding, single-lane ribbon of pristine tarmac on some island in the Mediterranean, there are three distinctive Central Oregon road routes that often pop into my head and make me miss home a little more than I already do.

Favorite Routes

The first is the McKenzie Scenic Byway. As a Bend native who graduated from the University of Oregon, I always have to laugh at how every single one of my friends from this side of the Cascades refers to the route that connects these two communities as simply “McKenzie” and all of my friends from the valley refer to that same stretch of road as “242” (its highway number). Despite which name I prefer, those friends from “over there” undoubtedly have the superior approach. Although it makes for a long day, and it’s not as often accessible from the east side, the western slope of that road is really what makes it so special for me. Between the perfect 6-7% gradient, the switchbacks, and the contrast between the lush forest and the arid moonscape up top, the west side of McKenzie Pass leaves the eastern approach in its shadow.

The next is the Crooked River Highway and Prineville Reservoir climb (or “27” to all you valley folks). The twisted, mangled junipers that line this roadway, mixed with the unabated sun exposure and the impressive climb to the top of the canyon past the reservoir makes this distinctive High Desert road ride a classic for many of us. It’s so distinctive, perhaps, that it’s left a brand in my memory — one that calls on my conscience every time I stray too far from home. Even if that 15 miles of seared, straight, pock marked chip seal on the return to Bend is enough to make anyone question their motivations, the undeniable beauty of that Cascade mountain view straight ahead of us the entire time seems to make it all worthwhile.

The third shouldn’t come as any surprise to any of us familiar with this event. One of the crown jewels of this region is Smith Rock State Park. Even though the roads approaching the edge of that park are pretty plain, the view they bring us is perhaps breathtaking for first timers and regulars, alike. The fact that many of us who participate in the Tour des Chutes get to help support cancer care and survivorship in our community and bask in the glory of this great natural formation (and maybe a dozen Joes O’s) at the same time is truly remarkable.

~Dillon Caldwell

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