Roadside Diaries: Central Oregon + Diving Into The Deep End

“Hey. I have an idea.”

Man, do my friends ever love it when I chuck that in mid-conversation. They tend to brace themselves a little, already accepting of the fact that that statement is usually followed by some ridiculous scheme I’ve impulsively hatched from mid-air. And you know how much I love adventure scheming. A few weeks back, I had messaged my friend J out of the blue asking if I could come visit him in Bend. He said yes. I was half kidding at the time, but sure enough, as soon as the idea had bubbled up, it took on legs of its own and ran wild. I found myself jetting down to Oregon for a brief stint in the high desert a couple weeks later to run along with it.

So, here’s a fun social experiment: would you commit to spending an entire day with someone you’ve never met in person, or barely know? How about five? A week?

Under normal circumstances, we’re used to getting to know someone slowly over time, in carefully managed settings. It’s safe. Measured. Calculated, even. We ease in a couple hours at a time, wading slowly, able to make an excuse and tap out at the first hint of things heading awry. For the most part, society doesn't really embrace the all-or-nothing, go-big-or-go-home mentality. We get to know one another in controlled environments wherein the other person chooses exactly what to allow us to experience. Nothing more, nothing less, almost akin to cautiously peeling an onion at your own leisurely pace. You can dip your toes in to test the water, and jump ship if things get uncomfortable. Rarely do we smash right into the onion or dive head first into murky waters. 

Spend six days non-stop with a near stranger, away from home and everything else of known comfort, with no exit door in sight, and that’s what you get. A smashed onion, a nose dive, and one hell of a gamble – all in the best possible sense. I can’t believe I’m still using an onion analogy, but here we are.

Some peculiar shade of magic reveals itself when you immerse yourself wholly in someone else’s presence. There’s nowhere to hide. Not at 5AM every morning when the alarm goes off. Not when you both haven’t eaten in 10 hours and have many more kilometres to go before that pizza you've longingly discussed for the last hour. Not when you’re locked in a car together for hours on end, or when the moods set in, or when you’re exhausted, lost, angry, annoyed. You get the beautiful, the good, the bad, the ugly, the imperfect. The human-ness. You get seen - no smoke and mirrors. And that’s where the beauty lies.

The Highlights

Toketee Falls {which is a Chinook word for graceful – much unlike what you might choose to describe how I looked attempting to scramble down a weathered rope to the falls} is a stunner of a waterfall on the North Umpqua River at its confluence with the Clearwater River. Carved from ancient columnar basalt, this place feels a touch like finding yourself in The Land Before Time, minus Little Foot and the squad {unfortunately}. Awe-inspiring would be an understatement.

Next, we took a drive down to Crater Lake. The smoke from the fires clung heavy above the lake, making for a very hazy view, but it was stunning nonetheless. What came as an unexpected surprise were the thousands upon thousands of California Tortoiseshell butterflies fluttering through the thick air before us. Oregon has experienced an unexplained boom in these beautiful little things as of late, and we were surrounded the entire way from Toketee to Crater. I'll leave it at that and glaze over the slightly traumatic fact that a good amount of these little guys ended up splattered against our windshield and bumper. Fun fact: Crater Lake was formed from the collapse of a stratovolcano named Mount Mazama after a massive eruption thousands of years ago. It took around 250 years of rain and snow accumulation to fill the caldera with what is now seen as the lake. Neature is pretty cool.

Smith Rock State Park. Up before the sun every morning, our days kicked off at 5AM to afford us some exploring time before the blistering heat set in. We reached Smith Rock just after first light, golden rays soaking the sheer cliffs of tuff and basalt. Nestled near Redmond and Terrebonne, this park has stellar rock climbing and bouldering and is home to a number of scenic hikes. We spent most of our time here walking along the Crooked River {mainly due to the fact that I’m still the frustrated owner of a sprained foot} and admiring the dizzying cliffs towering above us. I’d love to come back one day and hike Misery Ridge along with a few others, preferably for sunrise. You can scope out all the trail options here

Chasing sunset up Pilot Butte. Both of us were dragging by the time evening rolled around this day, exhausted from the heat and long hours spent in the car, so much so that we nearly skipped sunset. It was a last minute push to get up and out of the house, and we were beyond stoked that we pulled it together and went. A quick drive within city limits or a light hike up along the trail, Pilot Butte is an extinct volcano sporting 360 degree views of the surrounding peaks and hills, with Bend resting tucked in around its base.


+ Sparrow Bakery - for its breakfast sandwiches which we ate repeatedly, and apparently for their ocean rolls, which I didn’t get a chance to try this time around {deep regrets}. It seems they’re amazing enough to warrant being shipped overnight to a different state as a birthday present, so there's that. Please report back if you’ve tried one!

+ Spoken Moto. What was once an old, forgotten mechanic's shop known in its day as the “Pine Shed”, is now a restored cafe and gathering space home to many gorgeous renovated vintage bikes. Motorcycles. Beer. Coffee. We spent a couple hours here hiding from the relentless sun, and I'd easily have stayed all day. Bliss.

+ Cascade Lakes Scenic Byway. We took an early morning drive alongside the rising sun to scope out this lovely road and the string of stunning lakes sprinkled around it. A vibrant emerald green Devil's Lake, picturesque Sparks Lake, Elk Lake, and the list goes on. Well worth a visit. 

Here’s the thing. If you look closely, you’ll see the light catch those minute intricacies that weave themselves into the foundation of others and make them who they are. The ones you wouldn’t normally chance upon under normal circumstances of carefully portioned interaction. Maybe it's the way they slip their feet out of their sandals to stand barefoot on the hot pavement any chance they get. Or the way they have, in fact, a hundred different smiles, each reserved for something different. The way they react to a sunrise, or to getting lost, or how they handle unravelling plans and chaos. You’ll see each facet of their personality, their moods, their finesses and subtleties, with no time-outs or space. Want to bond with someone? Like, really get to know them? Travel. Experience something new together. Put yourself into potentially uncomfortable situations just for the hell of it. Stick it out, in all its imperfect flaws. Take a risk and send it full tilt.

Since you're probably wondering by this point, no, we didn't strangle each other in the end.

And yes, we had one hell of a rad time.