Shae, Truffles and I spent mid-October to mid-December in Oregon, having postponed that from our original plans to spend the summer there.
We didn’t pick the greatest time of year to visit weather-wise which meant we were less inclined to spend a lot of time outdoors, plus snow meant there were some places we weren’t able to access. It also didn’t help that Shae had to have emergency gall bladder surgery during our first week in the state which affected her ability to go out and do activities for several weeks after that.
Despite the timing not being perfect, it wasn’t all bad. Here’s a list of our favorite – and not-so-favorite – things from our two months in Oregon.
Favorite Accommodation We Stayed At
Stephen – It was nice being in a one bedroom Airbnb for a month in Portland, but the Holiday Inn Express Bend wins this category because it was such a lovely stay. The staff there were incredible – just the nicest, most helpful and genuinely kind and friendly group of people from the front desk to maintenance to the breakfast team.
Their hot breakfast was also good, the hotel was great value when using points and our room was decent too.
Shae – Hands down the Holiday Inn Express Bend, for all the reasons Stephen mentioned above, but an honorable mention goes to the Duniway in Downtown Portland for a few days. It was beautifully appointed and was really fun to be right in the center of the city.
Favorite Meal
Stephen – PDX Sliders in Portland. My burger and BBQ sandwich were some of the best burgers/sandwiches I’ve ever had.
Shae – Ohhh… such a tough call. PDX Sliders were so good and the Truffles Fries…. *drool* but I also really enjoyed the brunch we enjoyed on our first day in Portland at Screen Door. While we didn’t eat there for brunch, we also enjoyed a drink at Cafe Zeus and the Hot Toddy was so fabulous I went back for another a different day!
Most Disappointing Meal
Stephen – It wasn’t necessarily the worst-tasting thing, but Blue Star Donuts in Portland was disappointing. They supposedly rival Voodoo Doughnut but there really wasn’t anything special about the two donuts I got. I don’t think I even finished either of them and I’m someone who normally doesn’t like letting food go to waste.
Shae – I expected Voodoo to be the one we’d put here since we weren’t impressed when we tried them before, but they were really good in Portland. I loved the Mexican Chocolate donut at Blue Star but I wouldn’t say it was the most disappointing. My most disappointing meal was the burger from The Main Place in Halfway since it was the final meal before my downward spiral into my gallbladder issues, surgery and recovery.
Favorite Free Activity
Stephen – Visiting Multnomah Falls. It’s so beautiful and we visited on a quieter day which meant we didn’t have to endure looking at Instagrammers gazing wistfully at the falls for a few seconds to get their perfect shot.
Shae – Visiting the Last Blockbuster on the Planet. That was just the perfect blend of nostalgia and quirky to take it over the top from the views of all the falls. But the free tour at the Tillamook Creamery was also top notch!
Favorite Paid Activity
Stephen – This is a tough one as there isn’t really one specific activity which stands out. The High Desert Museum was a great museum in Bend, but Smith Rock State Park might edge it out for best paid activity. Although it was in theory free to visit the state park itself, there was a $5 parking fee.
Shae – I’d have to agree that the High Desert Museum was probably the best for me as well. I love to learn and there was a ton to explore and learn there. I had a great time trying ciders at 2 Towns Ciderhouse on our way out of Oregon too.
Favorite Pet-Friendly Activity
Stephen – Cannon Beach on the west coast while we were staying in Portland. Truffles loved running around and chasing after her ball for a couple of hours on the beach.
Shae – Awww definitely Cannon Beach. I almost listed as favorite free activity too. Truffles was just living her best life there!
Least Favorite Activity
Stephen – Driving through a winding canyon in the dark in the early hours of the morning having had no sleep to the ER while Shae’s writhing in agony in the passenger seat of the car.
Shae – The sickness and removal of my gallbladder in Oregon. Ugh. Thanks Oregon.
Favorite Hike
Stephen – Smith Rock State Park. It was so beautiful and peaceful there.
Shae – The day we went to Newberry National Volcanic Monument near Bend where we saw the volcanic area and the snow!
Favorite Quirky Thing We Did
Stephen – Visiting the Last Blockbuster On The Planet.
Shae – The Last Blockbuster on the Planet was probably the quirkiest thing we did and best!
Favorite Memory
Stephen – Getting to meet up with our friends Mark and Megan several times in Portland.
Shae – Oh man, getting to see our long-time friends and travel buddies Mark and Megan – but also meeting new friends like Heidi, Josh and Kara.
I also loved learning about the American Larch which is a deciduous conifer (an evergreen that changes its needle color each fall) and teaching that fun fact to all my students and showing them the larch smiley face.
Funniest Moment
Stephen – I know we had some funny moments, but I’m struggling to think of any in particular.
Shae – Seeing Truffles’ new friend Charlie confused about coming with us (his new friends) and his pawrents who continued down the beach! He was like “wait… where’s the fun and friends going?”
Thing We Most Regretted
Stephen – Visiting while the weather was so bad. We’d postponed our summer visit as accommodation prices were so expensive, but I think we would’ve had a much more enjoyable couple of months visiting when the weather wasn’t so dreary for much of our time.
Shae – Getting quite a small Airbnb. In theory it was great since it was so close to downtown but without a little more space, bad furniture placement and no laundry it was just not very fun to be there for a month.
Something We Missed And Want To See
Stephen – Crater Lake National Park. The roads in the park closed just after we got to Bend, so we plan to return to check that out.
Shae – Crater Lake for sure and the Oregon Trail Interpretive Center that as closed for renovations.
Our Biggest Surprise
Stephen – How nice Portland is. While the weather wasn’t great, we didn’t feel like it was unsafe and there’s so much beauty there contrary to what some media outlets might try to say.
Shae – How much I didn’t care for Oregon. I thought I’d really like it, despite the weather, but it just isn’t my jam. Sorry Oregon! I mean you’re no Connecticut but… close.
My Oregon Drinking Game Would Be…
Stephen – I actually have three Oregon drinking games. Take a drink every time you:
- See a brewery (there are tons of them all over the state and it makes it much easier to do a drinking game 😉 )
- See something relating to Bigfoot/Sasquatch (Oregonians love themselves some Sasquatch)
- See a waterfall (there are almost 250 of them, but that’s apparently quite low compared to many other states)
Shae – Um… hubs took them all apparently.
I’d say take a drink every time you see a brewery in Portland. They love them some craft beer there too.
Summary Of Oregon In 10 Words Or Less
Stephen – Lots of beauty but also lots of rain.
Shae – Nice enough but mostly trees, not Connecticut but close.
Oregon Cities We Visited In Order From Favorite To Least Favorite
Stephen – Portland, Bend, Halfway
Shae – Portland, Bend, Halfway (it’s really pretty there though so it’s more like tied with Bend for me)
Edmund Welter says
Too bad about your experiences in Oregon. Really, September would have been the optimal month for weather and costs. But even in September Crater Lake is a hit or miss. We went there in August once and it was snowing and you couldn’t even see the lake. But you missed Silver Falls State park, Sea Lion Caves, doing the Rogue River, Ashland’s hippy vibe and so many outdoor experiences to mention.
stephen says
Thanks for those extra suggestions – I’ve added them to our list for if and when we head back to Oregon in the future.