Yup, I will be Oregon gone gone again in just over a week. I’ve booked vacation from May 23 to June 2, 2023.

Monday, May 22 is Victoria Day, a stat holiday in Canada. Anytime a long weekend is involved, it’s a good idea to stay away from the border. I’m not sure what my strategy will be. Maybe even wait until May 23 to head south.

The flip side is that Memorial Day in the states is always the week after Canada’s Victoria Day, in 2023 falling on May 29. I’m trying to squeeze myself inbetween the two long weekends on both sides of the border. Mostly I want to avoid long border line ups. Two hours wait or longer is not uncommon on long weekends.


Do I have a plan or will I do my usual fly by the seat of my pants thing? I’m good at winging it.

Practicality also grips me. Whether you call it Victoria Day or Memorial Day, it’s the unofficial kick off to summer. People are on the move around long weekends and booking hotels in advance.

Here’s a loose plan of activities, including known hotels I want to stop at:

  • Horseback riding on the beach
  • Lincoln City
  • Bowpicker Fish and Chips
  • Depoe Baykery
  • Bend
  • Painted Hills
  • Cranberry Sweets
  • Walk on Seaside Beach
  • Walk on Cannon Beach
  • Ester Lee Motel
  • Wild Horses Monument
  • Visit Tillamook Creamery
  • The Boat Fish and Chips
  • Ride a dune buggy
  • Appaloosa Museum
  • Hotel McCoy Pullman
  • Coos Bay

Originally I was thinking of ending my trip on the Oregon Coast. Now, I’m thinking of beginning my trip on the coast. It all comes down to making sure I get to the Depoe Baykery and it’s closed on Mondays and Tuesdays. It’s the best bakery in Oregon. According to me and Taste of Home magazine.

Painted Hills

I’ve never been to Painted Hills in Oregon. They’re part of the John Day Fossil Beds.

In 2018, I was planning to do a day trip from Bend, but I was too tuckered out from driving from Crescent City, California, circling Crater Lake, and finishing in Bend.

Too ambitious!

This time I’d like to visit, though I’m a little foggy on the directions. The Painted Hills are about 75 miles from Bend, Oregon. I can’t get a good reading on them from my GPS here in BC, but I recall the last time I was in Bend I got better directions. Oh well. I’ll worry about it later. This is the reason I’m thinking it’s better to do the coast first and then head inland.

Photos courtesy Pixabay.


Moscow, Idaho

I have a few things in mind. I plan to visit Moscow, Idaho. Yeah, I know, not Oregon.

And, no, not planning anything gruesome like a drive by of that house where those four university students were slaughtered last year.

I want to visit the Appaloosa Museum.

Probably not a big highlight on most traveler’s itineraries. Unless, of course, you love Appaloosa horses!

Cheryl @ The Lifestyle Digs Favorite Things 2018

I love spots!

I’ve known about the Appaloosa Museum for a long time and wanted to visit it. Now seems like the time to throw in a weird side trip on my Oregon vacation and do it.

With my upcoming exit from Canada, it might be now or never.

Kind of a tribute to my beloved Appaloosa, Whistler. RIP.

Also. there’s a Shari’s restaurant next to the museum. I have to stop for lunch somewhere!

The Hotel McCoy in nearby Pullman, Washington looks pretty cute and I’ll probably spend the night there.

Wild Horses Monument

Photo courtesy Washington Trails Association.

I’ve driven by the Wild Horses Monument a few times. It’s very visible for miles along the highway.

However, I’ve never stopped and hiked up to the monument. This is the trip where I’ll do it!

I have to get in the training for walking the Camino de Santiago.

Going to be Oregon gone gone

So there it is. My very loose itinerary for driving around Oregon, Washington, and a bit of Idaho.

There are things I want to do, places I want to eat at, and hotels to stay but I haven’t put it all together yet. I probably won’t even figure out if I’m heading south or east to begin. I like the idea of ending my trip on the Oregon Coast, but I have to keep in mind the opening hours of some of the places I want to stop at. Going east and then coming back west might be more convenient.

Nothing like flying by the seat of your pants!

Road trip and adventure await!

I will be Oregon gone gone again!


Published by Cheryl @ The Lifestyle Digs on May 13, 2023 and updated on June 13, 2023.

And here it is, photos and itinerary of my Oregon road trip late May, 2023.

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