At long last, my years-long dream of exploring and sleeping in the wilderness comes to pass.

At this point in my nomadic journey, I’d spent a whole month (March 2025) on the road…yet I felt like I didn’t have much to show for it in terms of the kinds of experiences (and let’s face it, photographs!) you can only get when you truly live as a cross-country nomad. For the most part I’d stayed near major urban centers in Oregon & Washington, and while I’d enjoyed a fair degree of nature experiences, I didn’t feel like I was living out in the wild, man…like the true hippies do.

This was all about to change. And I got the cover photo (above) to prove it!

Hipcamp is the Hip Camp

Where last we left our intrepid hero, he (I) was just returning from a fun touristy time in Seattle hanging out with my brother Shayne. But my adventure was just beginning, as I decided it was time to head the opposite direction and go south (and a bit east) in search of what I hoped would be an epic trip through the rugged high desert regions and eastern slopes of the Cascades in central Oregon.

But first I had to get through the Cascades, so I began my travels heading east from downtown Portland, stopping first for a leisurely afternoon respite at Blue Lake.

Such pristine waters

From there I made my way out along Hwy 26 and southeast towards the small town of Sandy, a well-known gateway to the stretch of highway which leads directly to Mt. Hood. I had decided to stay the night at my first Hipcamp ever, out in the foothills past Sandy.

For those unfamiliar, Hipcamp is essentially an “AirBnB” for camping. You can browse through listings of all sorts of camping destinations largely run by private operators (in many cases people who own homes on acreage and offer a portion of their land to be used by campers). Check out photos, read reviews, and when you’ve found the perfect spot, book online quickly and easily.

I was rather nervous about finding “the right place” to stay the night car camping for the first time, but I shouldn’t have been. As soon as I arrived, the owner of the property aka the host came out to greet me and walk me through the basic aspects of the property. It was gorgeous! And in addition to the cleared space where cars, vans, & RVs can park, it turned out there was a walking path through the forest in a loop around the perimeter. Was this my first time hiking through a privately-owned nature park? Could be!

Left: Sit a spell and enjoy the solitude of the ferns and the trees
Right: I was a happy camper…literally!

A quiet path all to myself…incredible

After exploring a bit, it was getting dark so I went back to my car and got settled in for the night. Even though technically it was now springtime, the nights were still quite chilly and the air was damp so I tried (and mostly succeeded) to stay warm and dry.

In the morning I woke up right at the crack of dawn—and let me tell you, there is nothing like beholding that magical moment when night gives way to day while you’re camping in a forest. Nothing like it at all. I simply live for forest mornings now. My oh my.

Anyway, I packed up and made my way back to Sandy, and after grabbing some coffee and a muffin, I had an inkling to explore just a little bit more on the edge of town before pointing the car towards Mt. Hood. And I’m so glad I did, because I found a quaint little country road heading north from the town and OH MY GOD OH MY GOD OH MY GOD!!!

Pinch me, is this for real?!

Spread out below me to the east were rolling hills and valleys laden with dense fog banks, and past that, the mountain. It was out, as they say here in the PNW. Not only was Mt. Hood out in all its glory, but the most incredible shimmering sunlight was streaming down past the mountain and onto the fog and it was a thing unlike any I had ever seen; thankfully I had a lens on me for my Nikon Z fc to capture some measure of the magic.

This was the cover photo you already saw, but it bears repeating!

Over the Cascades

With that rousing start to my journey, I drove onwards east to Mt. Hood. I stopped at the town of Government Camp, a sort of waystation for explorers of the mountain. At this elevation, I was starting to see clumps of snow here and there, but thankfully no dangerously slick ice.

Quick stop at the general store

Still a bit of a wintery vibe here

I soon continued on my way, heading east and soon southeast along Hwy 26. I must confess, some parts of the road here going through the mountainous terrain get pretty monotonous. Mostly all fir trees, all the time. But once you get past that and into the drier areas, you really feel the change of biome as the terrain gives way to the high desert of central Oregon!

The road to Madras, OR

Let me say a few things about desert. I’m not really a “desert guy” at heart. Yes, I have traveled pretty extensively throughout the American Southwest. I’ve driven through California’s Mojave Desert, I’ve been in and around Las Vegas, Nevada, and I’ve stayed at various times in Arizona, New Mexico, and Texas. It is not my scene. In fact, in New Mexico some years back I had a variety of bad personal experiences such that I doubt I’ll ever go there again. (Santa Fe is a lovely town, I’ll grant you that.)

All that to say…I love the Central Oregon desert! 😄 Place your finger on the map right at The Dalles (or just east of it where the Deschutes River meets the Columbia) and trace a line straight downward all the way to Bend, OR. This whole region simply slays. I mean, sure Montana is “Big Sky Country” but, like, we got that right here in Oregon.

I actually took this in February 2022 but…yeah 🤩

Deschutes…More like DeWOW

On a whim, I decided to head off the main highway a bit before Madras and follow the Deschutes River south. So much of what makes the Oregonian landscape iconic are its many outstanding rivers, and the Deschutes is no exception. I hadn’t spent a whole lot of time around it other than in Bend previously, so this was the perfect opportunity to experience more of it.

Almost immediately I was graced with an incredible view of the river as it bent towards a reservoir.

There's a wonderful and roomy parking area overlooking this scene

After following the river a ways, I ended up wending my way through BLM (Bureau of Land Management) land which truly felt like the middle of nowhere…in a good way. I found a glorious dirt road to park on so I could take a stroll through the grasslands, and this vista of Mt. Jefferson to the east simply took my breath away.

Very Wild West vibes out here

By this point, I was already quite satisfied with all the landscapes I’d seen on my drive, but the best was yet to come!

I continued wending around on whims in a southerly direction close to the Deschutes River, when purely by accident, I stubbled onto a landscape so unexpected, so mind-blowing, my jaw hit the ground and rolled off over yonder somewhere.

Apparently Oregon has its own little "grand canyon" and no one told me?!

Photos just can't do it justice…this view felt positively MASSIVE

Now when I say my jaw fell, I mean I was literally standing at the cliffside with my mouth agape looking like a maniac and this continued on for some while.

Not the most flattering selfie, but I was truly dumbfounded, flabbergasted, and hit like a ton of bricks!

Truly the highlight of my day, once I’d regained my composure I continued south in a leisurely way, eventually merging onto Hwy 97 and reaching my principal destination: Bend, Oregon.

How Come the Badlands are So Good

After spending a restful night at a modest hotel and getting some computer work done in the morning, I was feeling greatly refreshed and ready to head out to the Oregon Badlands Wilderness, an area southeast of Bend which looked like a blank nothing on the map and seemed mysterious and intriguing.

I was expecting…well, I was mostly expecting what I’d seen much of elsewhere in the middle of the desert once you’ve left the Cascades behind: sand, grasses, tumbleweeds, flat terrain, and not much else. What I saw instead completely blew me away.

I was not prepared for this

I suppose the badlands would hit differently in late summer when it’s ridiculously dry and hot out, but at this time of year with so much snow lingering on the paths, it felt almost verdant. Juniper trees abounded, along with craggy lava rock formations and an undulating, otherworldly landscape.

Left: Holey rock formation
Right: The vibes were immaculate

There are nearly 50 miles of easy walking trails here…truly a place to get lost in the best possible way

Yours truly with a big smile on my face

Left: I feel like this is right out of a coffee table photo book
Right: Another gnarly old juniper

I hated to leave, I could have spend much more time here; but duty called and I had to head back to civilization to get a bit more work done. However, that didn’t stop me from later finding another park area closer to Bend, OR for a good ol’ stretch of the legs.

I love this quote

Back in Bend, I picked up some grub at the most excellent Grove, a food hall with multiple restaurants and an excellent coffee shop (Thump Coffee).

The outdoor seating area was quite lovely

Fancy fancy

Achievement Unlocked: Dispersed Camping

At this point, I decided to be bold and try something I’d never done before. With apps like The Dyrt and iOverlander in hand, I made my way west into the mountains and the ponderosa pine forest, trying to find a dirt road I could follow to an area good for dispersed camping.

The first location I found on the map appeared closed, but I continued on a little farther and found an absolutely stellar road. In surprisingly short order, I found my camp spot for the night. A few other folks were scattered about nearby, clearly fellow nomadic travelers. I didn’t quite work up the courage to go up to anyone to talk, but they left me alone as well so it was all pretty chill.

And oh wow, my dream of walking through and staying in a ponderosa pine forest was finally coming true. 😍

The view outside my "bedroom" window for the evening

Blissfully awakening the next morning

I’ll have a lot more to say about how fantastically awesome the ponderosa pine forests of the eastern Cascades are later on, but suffice it to say, I was rather pleased with myself that I’d managed to sleep out in the wilderness on public lands with no issue. I’d done the thing I’d seen so many “van lifers” do on YouTube. Now I could count myself among them. Wowee!

I headed back into Bend for a mostly uneventful day of working in coffee shops and libraries and such, but not without a bit of exploring around the Deschutes River in town.

A tranquil lazy river

Left: A delightful walking bridge
Right: Hey, it's me again

An Unexpected Lakeside Campsite

After wrapping up work for the afternoon, I had an itch to explore even farther to the east…what might I find past the badlands on the other side of the plains? I had absolutely no idea what was out there which honestly is the best way to travel.

As I approached the town of Prineville, I took the viewpoint exit and ended up atop Ochoco Divide at Ochoca Wayside State Park with a grand landscape stretched out below.

It's like SimCity in real life!

Scrambling over rocks on the bluff

Trying to figure out all the different mountains and mountain ranges

Exciting stuff, but now that I’d seen how the plains were giving way to rugged terrain, I wanted to see a little more, so I found a road to take me east into the Ochoco mountains. I didn’t have to go far before I came across an absolutely stellar place to set up camp for the night, Ochoco Lake County Park.

I had such an incredible stay here, I would drive all the way out here from Bend, OR just to spend another night by the lake. 😍

Dazzling clear reflective waters

Night descends on the lake

A truly magical way to awaken

Left: Goooood morning!
Right: The last selfie of this travelogue installment, I promise!

After daybreak, I had a clear idea of where I wanted to go next: one of my absolute favorite little towns east of the Cascades, Sisters.

Sisters, Ponderosas, and Bidding Central Oregon Farewell (For Now)

Sisters, named after the “Three Sisters” mountains in the Cascades, is a charming, western-style town nestled in the thick of the ponderosa pines. I’d always been mesmerized by the pine forest in this area; that expansive feeling you get due to the fact that the trees are spaced relatively apart from one another and there’s not much in the way of underbrush. You can really see through the trees, and I’d always wanted to explore more.

But past trips through Sisters I was on my way to another destination (usually heading towards or coming back from Bend), so I had yet to check off my bucket list item of hiking through the pines. This time, I was going to do it! But first, I had to make a stop at my favorite spot in town: Sisters Coffee Co..

Left: Family owned since 1989
Right: It's not technically a selfie, right?

Once I’d enjoyed a fabulous cup of coffee and gotten a bit of work done, it was time to seek out a trailhead and hike through the ponderosa pines. And oh wow did I feel like a dope for not doing this a lot sooner…turned out a great trail (Peterson Ridge Trail) was mere minutes away from town!

A dream come true

Strolling through the pines

Left: The Leaning Tower of Ponderosa
Right: I just love the rich rust color and texture of the pine tree bark

A few gnarly junipers in the mix as well

An open, sunny path…just incredible!

Sometimes you build a future vacation destination up in your mind so much, and then you get there and it’s a bit of a let down. Not so with this trip. I had an absolutely incredible time in Bend, Sisters, and beyond…even more than I was expecting. And the pines in particular—oh I was smitten. So smitten in fact that I would return again…but that’s a tale for another time.

Eventually I made my way back to the car and started to head back over the Cascades once more. Circumstances required me to arrive once more in the Portland area, but if you think this meant my nomadic adventures had come to an end…most certainly not. I’ll pick up right where we’re leaving off in Part V of my travelogue, to be published later this month.

I hope you enjoyed this installment all about central Oregon! ✌️ Check back soon to pick up the trail.

Oregon's "Matterhorn" in the guise of Mt. Washington (alas, lots of fire damage in this region)

#nomadlifestyle #oregonexplored