Okay, so the idea of checking out Oregon popped into my head sometime late last year. Saw some photos online, you know, the usual stuff – coast, forests, looked pretty amazing. Decided maybe 2024 would be the year to actually make it happen, not just think about it.

First thing, I jumped online. Typed in the usual stuff, “best places Oregon,” “Oregon trip ideas.” Got flooded with all these slick travel blogs and booking sites. Honestly, it was overwhelming. Too many “top 10s” that all listed different things. Felt kinda fake, didn’t really give me a good feel for planning it myself.
Getting Down to Basics
So, I ditched the fancy sites. Went back to basics. Pulled up some maps online, just looking at the state itself. Realized pretty quick how big it is. You got the coast, then the mountains, then the high desert way out east. Can’t just hop between them in an afternoon.
Okay, gotta narrow it down.
- The coast definitely looked cool. Cannon Beach, Tillamook, all that.
- Then there’s Portland. Heard mixed things, but figured it’s worth seeing. Food, weirdness, you know.
- And Crater Lake. Pictures look insane. But it’s kinda out there on its own.
- Bend seemed like a hub for outdoorsy stuff, mountains, beer.
Started trying to piece together a route. Maybe fly into Portland, rent a car, do a loop? Coast first, then maybe head south towards Crater Lake, loop back up through Bend? Immediately saw the driving times. Yeah, this wasn’t gonna be a quick weekend trip. Needed to block out real time.
The Details Get Messy
Then I started looking at when in 2024. Summer seems obvious for weather, right? Especially Crater Lake, road might be closed otherwise. But then everyone goes in summer. Prices go up, places get booked solid. Looked into shoulder seasons, like late spring or early fall. Weather’s more of a gamble, but maybe fewer crowds? Still trying to figure that sweet spot out.
Accommodation was the next headache. Hotels, motels, Airbnb, camping? Prices seemed all over the place. Some spots, especially near the popular parks or coast towns, looked like they book up months, maybe even a year, ahead for summer. Found some cool-looking cabins but they were either way out of the way or cost a fortune.
Where I’m At Now
So right now, I’ve got a list of places I want to hit. Got a couple of route options sketched out on a map, depending on how much driving I’m willing to do each day. Still haven’t locked in dates, kinda waiting to see how work pans out and maybe find a slightly less crazy expensive time to go.
It’s more work planning this than I thought it would be, honestly. You see the nice pictures, but figuring out the actual logistics day-to-day, where to sleep, how long it takes to get places – that takes time. But, hey, doing the digging myself feels better than just clicking some pre-packaged tour. Got a better feel for the place already. Still looking forward to it, just gotta nail down these last few details.
