The Forts of Oregon Country

Booking the last two stays — The Dalles and Oregon City Portland — was trickier than usual. We were spoiled for choice, which led to great indecision. Then we ran into a few bumps. We found a house on a hill in The Dalles that fit the budget and caught our attention because of the name, so we asked ChatCPT to make us an intro:

Another introduction letter I did not send.

But ultimately that reservation didn’t work out, but Plan B ain’t too shabby! And we’ll have two nights in the area to explore as we prepare ourselves to float the Columbia or decide to take The Barlow Road.

In Portland, we had far too many options. Ultimately, while staying somewhere historic in Oregon City would have been great, we needed to be central enough to be able to host a car sale and then get around town with a dwindling number of vehicles.

But if the reader will allow one more trip down “what could have been” lane: we did find a massive themed listing on a ranch southeast of Oregon City called “End of The Oregon Trail Experience.” Had money (and logistical considerations) been no object…

At first we couldn’t tell what we were looking at. Was it a game room? Was this something on the property? A nearby attraction? No, the indoor space is an entirely themed “old west” town. The four bedrooms are The Jail, The Brothel, The Lewis & Clark Headquarters, and The Cowboy Room. Other amenities include a bar and big gaming table in The Saloon and a 12 foot projector screen that comes down in the middle of town square (the open space between each of these rooms). All of this sits on a 15 acre farm that also has some wildlife. Guests receive a carton of farm fresh eggs from hens on the property as well as an opportunity to meet an Emu! Alas, just out of reach.

Instead, we’ve found a restored Craftsman house just off Division Street, near many of Portland’s popular restaurants and bars. Sears catalog homes may be about 100 years out of date for our 1800s adventure, but we’re already bending the timeline, what with the horseless carriages and all. And reading between the lines of the listing, we’ve discovered that this home is owned by a local author, so that’s nifty!

I haven’t been back to Portland since 2019 while still working with Four Kitchens and our client-at-the-time, Oregon Public Broadcasting. (Which, given our history with car sales… I might have to look up the contact I had in vehicle donations to be on standby…) So I am very excited to visit again.

Independence. Again.

And in the middle of all of this, I got a notice that our starting line house in Independence, Missouri had to cancel on us. And on everyone else. Apparently there was a neighborhood dispute about short-term rentals… which… well… I have conflicted feelings, despite being a rather frequent tenant. So we went back to the catalog and found this delightfully historic mansion at the intersection of “Interesting” and “Affordable-ish,” I present the “Fully Restored 1885 Queen Ann:”

It far out-specs our true needs, but there weren’t a ton of options in Independence with less than a month to go. And it was less expensive than some of those. We will have one office day and some initial car tinkering to do here, and there’s plenty of space and a garage. So I’m pleased with out choices.


And with that, we’ve mapped out all the forts and settlements across the great frontier to Oregon Country. This might be our bet set of accommodations yet.