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Oregon’s Hidden Gem

I am surprised that there is technically only one National Park in all of Oregon. I think of every state that we’ve visited, it had the most diverse landscape to encompass just about everything from very steep mountainous peeks to arid, dry, deserts, plateaus of interesting canyons, tall rocky features prime for climbing and so much beauty. And while Crater Lake would be awesome to visit, we didn’t know exactly how it would fit into our path.

We knew that we wanted to explore the region, just none of the specifics. After yesterday’s less than stellar results, we finally got the message that we needed to start planning a little better having booked the next several days of camping.

Kelso was the perfect reprieve and we were not in any particular hurry to hit the road, so we took our time enjoying the surprisingly delicious breakfast of burritos, omelets, sausages and lots of other yummy foods available. I glimpsed at the map to see where we were heading, and realized that we would have to pass through our old alma-matrimonial-site, VooDoo Doughnuts, in Portland. By the time we figured that out, my mouth was watering for a delicious chocolate cake doughnut.


It was a quick in and out trip, but so fun to go back to the old stomping grounds and see how much the place has changed. The same old Kenny Roger’s illustration shined as well as all of the fun tricks and treats hanging up all over the place. It was nostalgic and the doughnuts were pretty delicious.

Onward to Cove Palisades State Park, we left the plains to climb the slopes of Mount Hood, which was absolutely beautiful this time of year. Our destination lays further south from the lush green and back to the barren, dry and open countryside. It was brutally hot and neither of us was super keen on camping in this heat.

We were only a few miles away and looking out in every direction was pretty much nothing but open desert sparsely populated with sage. I was beginning to worry that camping would be a tiny bit miserable, since there were no landmarks or features (or even shade) anywhere. We turned off the main road down a winding road and saw the first campground, which looked just like an RV parking lot with a few trees scattered. God I hope this isn’t our spot. I double checked to find our camping was in an area called Deschutes, still 4 miles away. On we drove and within a few bends, we found ourselves going down a steep canyon and the sight of a large green and blue river made its presence known. It was so lovely I was totally shocked and excited at the prospect now, because it only got prettier the more we drove. Our campground was beautiful, and had plenty of shade and a flat, well-maintained area.


It was early afternoon at this point, and Jake verified that 2 of the properties we wanted to scout were only a few miles from here, so we opted to go check them out before the evening. My high hopes dwindled as we drove out of the canyon, back among the flat and barren landscape. The properties lay just off the winding road and had very little in the way of anything. A few junipers and sage and a lot of dry sand. The only redeeming factor is that its cheap. But its totally uninspiring. We gave it the benefit of the doubt and walked around to see if there may be some hidden potential but came back with naught but lots of sharp, prickly plants sticking out of our socks. At least it was easy to find the properties, which is a small success.

Back at camp we enjoyed the evening, when it finally cooled down, though not quite enough for us to be comfortable in the van. Warm is an understatement. It was royally hot and bugs kept flying in buzzing around our ears so we opted to button down the hatches to bare the heat.

The next day, we drove out to Prineville, to check out a property that appeared to be in a beautiful state park, which was gorgeous, but turned out to be on the side of a very busy road, which isn’t appealing. We weren’t too far from Bend, Oregon, and thought that maybe we would take the day to go visit the town and then maybe check out another property 45 minutes south of there. Bend is a place that we are both a bit intrigued by, for its similarities to Boulder, yet it has more space and some variety. We grabbed a bite to eat at a trendy hipster-type restaurant called Spork, totally yummy. The vibe in town is really nice, and it would be cool to live near here, however its just too crowded and expensive for what we are looking for.

La Pine is the next city on our docket, and the drive out there was promising. We passed a MASSIVE state forest that felt like it went forever and was so lovely. The lot out here is a bit more expensive than Culver but has a lot more trees and is closer to Bend, which is a nice city. We had to break out the GPS to make it the last few miles, requiring a lot of driving down dirt roads. The instructions were very detailed and so we pulled right up to the sign that indicated the 40-acre lots available. There were several adjoining parcels, and it actually looked promising. We got out to walk around and though there isn’t much of a view, there were plenty of trees and forest and even power. I could hear the road noise in the distance, which is not a deal breaker, but not ideal.

This surprised me because it felt like we had to drive miles off the road to get here, so I did a quick hike past the property and beyond a few bends to find a fully developed neighborhood right next door! Now, most people might be excited at this prospect, but my heart sunk. There’s a paved road too! Its just way too close to everything and obviously not secluded like the listing stated.

Oh well, it is a bummer but it felt nice to see something that we sorta liked. Based on what we saw, we decided to skip the last 2 properties in Christmas Valley because they were much more reminiscent of the arid-desert of Culver than the rich green of the mountains that we like.

All-in-all it was a pretty decent success in that we found several properties and visited new areas of the state. The last and most promising portion of the land-hunt in Oregon is Enterprise. If looking on a map, it appears like it should be a quick and easy drive, however there is only one road in and out, due to the giant canyon that splits up most of the eastern part of the state. There is no way we could do that today, so we will dive into that when we go to Wallowa Park the next few days.

The next morning we took the beautiful and scenic Elkhorn highway along a small mountain range rooted with forests, grasslands and a large river. It was a bit of a haul, taking most of the morning and early afternoon to get there, but as we rolled up into Enterprise, we got excited. Just beyond we reached the small town of Joseph, Oregon and pretty much took the only road there to it’s finality, which happens to land in the Wallowa State Park.


Holy Cow, we were blown away. It was so beautiful, so perfect that I could barely contain myself. The massive mountains sprang up high out of the ground, and gigantic trees surrounded a big and beautiful lake. It was so reminiscent of New Zealand and for the first time on this trip, I felt like this could be home.

The campground was gorgeous too, and we just can’t believe we get to stay here! We hiked around and chatted to other campers in the area who told us that this is one of Oregon’s best kept secret (SHHHHH don’t tell). 😉


Camping was fantastic and we both slept great. I think the cooler temps really helped. The next morning we had planned to meet with a realtor in town, to discuss several of the properties that we were interested in viewing. He offered to drive us out to each of them, which is really great since this is the first time any realtor has offered to take us to a property. It’ll be nice to NOT have to drive down unfinished, unpaved, nightmarish roads for a change and actually see the property in question.

Kirk invited us in for a chat and informed us of 3 properties in the area that sort of fit our requirements. The first one is a lot very nearby, with 40 acres. The price, however, is 200K, which is WAY over our budget. But we figured it’d be good to see something nearby. The next 2 properties are a bit outside of Enterprise, specifically in Flora. They are both over 160 acres, and valued at less than $1000/acre, which is a really good deal.

The first 40 acre lot was quite beautiful, sitting on the side of a small mountain and boasted some breathtaking views. There was a large variety of terrain and usable spaces AND both water and power. There wasn’t a road, though one could be built for a mere $15K. I did a double-take when I heard this, since it didn’t appear that you needed more than a few 100 meters of road from the one we drove up, but that’s when Kirk proceeded to inform us about Oregon law. A road to any property has to be accessible by fire trucks (due to high fire danger) and therefor has strict codes of building. Basically you need to hire the city to build a real road for you which is why its so expensive.

That’s good to know, but kind of a bummer. We asked Kirk about some of the other laws/rules and learned that Oregon has a very strict and short hunting season, which is kind of silly due to its many resources abound and similarly to states like Montana, which is pretty much open hunting for 6 months of the year. Most properties are zoned for only one livable space, which doesn’t work with our plans to have a Bed & Breakfast.

Despite these drawbacks, the terrain is so lovely. After looking at the smaller lot, Kirk drove us out to Flora, which was about 45 minutes away, from which we drove around half of the 160-acre lot that just came on the market. I thought I knew how bit 160 acres was, but now I know that I was off. Way off. Its beyond huge…massive. So massive that it had 3 different “ecosystems”. First was about 30-acres of completely flat, open wheat field (bordering a neighboring farm). Another 40-50 acres was a mixture of meadow and spring, large pine trees and tons of open space for building. the rest makes up part of a canyon that spans for miles and boasts some spectacular views.

Both Jake and I felt that this was absolutely perfect for us. We’ve found it!

In my mind, the search was over. We only spent about 40 minutes walking only part of the lot and driving part of it, but we loved it.


Kirk took us to the third property, which was nearby and beautiful, but didn’t have the appeal of the second. On the drive back we were talking about what sort of things we needed to do in order to secure this deal. He said we could make an offer now, and sort of pushed us to doing that (he’s a realtor so naturally that’s his priority). But we had to think about it.

Back in Joseph, Jake and I went out to lunch to talk about this. Is this really something we’re ready to do? But then we got to thinking, how the heck are we going to buy this? Its very much out of the price-range that we planned and even if we could get a loan, we would be putting all of our eggs into this one basket. And more than that, we don’t even know this town or city or anything in or around it.

At this point we realized, or I realized, how little we thought this through. Are we ready to settle down here? Are we prepared to go back into debt on this property? Are we prepared to stop travel at this very moment?

These questions were difficult yet vitally important to answer. I certainly don’t feel ready to settle down just like that. I don’t believe that its smart to make such a big decision so quickly. What about Bosco boat? Unable to decide, we thought we needed a second opinion. So, Jake reached out to our buddy, Ed, to seek his advice. He gave us great perspective: “Don’t rush it. If the property is still for sale when you are ready, then do it, otherwise its not meant for you.”

Though its maybe not what we wanted to hear, we needed to hear it. I don’t think we’re ready to commit to anything so quickly.

That said, neither of us wanted to walk away from this either. So, we decided to go back the next morning to the property on our own to walk it and see how we feel. How funny is it that we created this trip of ours to find a new home and land to buy, and this is the closest we’ve come to pulling the trigger, and yet we never thought through the important details.

We spent the better part of 3 hours at the property, walking along the entire edge that didn’t go down into the ravine. I was blown away by its beauty, but I was also feeling the immensity of 160 acres of land. Its A LOT of land! Maybe too much for us to bite off in one go? We finished the perimeter walk and together took the rough, overgrown path down into the ravine. The temperature changed drastically and it dropped about 15 degrees, which felt quite nice. The trees were thicker and brambles were all over the place, sticking us left and right.

At some point we both heard the cry of a coyote, far too close for comfort, just over a berm. I wish I had something more than a stick for protection. Not long after, we spotted fresh bear scat on the track. So, we know animals are here and very close. That’s good, yet we were both scared too. So we turned back and headed to the safety of Blue, who was now totally covered in sand.


I think that perhaps this property, while beautiful and with so much potential, is a little too much for us to bite off. At least with regard to making a quick decision. Neither of us is sure that this is THE ONE.

I know, its silly superstition, but one funny thing that happened made me think that there was something to this. The big property in Montana that we really liked had a beautiful bright turkey feather laying out in the middle of an open field. We saved it and put it on Blue as a symbol of our trip. Well after we walked this property in Oregon a second time, I spotted another big beautiful turkey feather, like the first, in perfect condition. I picked it up and put it with the first. Maybe it’s a sign from the Universe that either of these properties is for us. Or maybe…third time’s the charm? Or maybe it means nothing at all. Its fun to ponder anyways.

Back to reality – while we love this property, I don’t think either of us is ready to commit to it yet. Maybe its not quite the right time but it forced us to make some important decisions.

And at that, we hit the road again on this journey to nowhere, unsure of our direction.

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2 comments on “Oregon’s Hidden Gem

  1. Wow you guys, this is a really funny. I can completely relate to making quick decisions without thinking about the finite details. Its nice to know that even avid travelers like you guys don’t let that hold you back from going forward. Very inspiring.

  2. Aww thanks so much! That means a lot.

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