Oregon Road Trip

My trip to Oregon was also my first time ever in the Pacific Northwest, and it surpassed my expectations. With five nights, I was very happy with the balance of city, waterfalls, and beaches we were able to fit in, and I was also thrilled with our early September weather. Nonstop sun in a place known for its rain and dreary weather? Blessed by the travel gods.

Day 1

Portland - City Exploration

A lot of Portland's reputation hinges on being quirky and weird, and I am happy to report that it lived up to every bit of it. I was absolutely thriving on the alternative feel of the city and would love to go back.

After landing at PDX, which looks like a shopping mall from the 90s, we caught the train into the city.

Expected to see a Sears

We were a little hungry and passed a Japanese sandwich shop called Tanaka on the way to the hotel that looked really good, so we popped in there. My spicy tofu katsu sandwich and black sesame maple latte were both incredible.

The hotel I chose for our two nights in the city was Mcmenamin's Crystal Palace, and I got caught up in a Mcmenamin's rabbit hole while researching. This is a whole collection of hotels in the Northwest, but each one seems really unique with its own theme. You can even get a stamp card to fill up as you visit all the Mcmenamin's locations.

Crystal Palace and their dining patio in the background

Crystal Palace is music themed, with each room named after a song. We got the Soul Meets Body room, which had the lyrics painted around the top of the wall and a headboard painting to match. I thought the room was great--I liked the red colors, there was a sink inside, large windows, and there were four private bathrooms on the floor, but the one right across the hall was usually empty anyway, so it barely felt like we were sharing.

Our first day was spent walking around the city to explore, and my immediate favorite thing were all of the cat statues. I think we found about a dozen before the trip ended, all painted differently. I'll spare you my photographs of every single one of them, but a few are scattered through this section. I also liked Portland's fun trash cans (this feels like a sentence I'm unlikely ever to write again).

We hit up an oddities shop called Skeleton Key, which also had a small museum inside...

...the world's largest indie bookstore, Powell's City of Books, which definitely owes its fame to size rather than any discernible charm...

...passed by Lan Su Chinese Garden, which we opted out of due to the entry fee...

Sneaky photo through the gates

...then walked to the river where we saw the Portland stag sign...

...and passed the Keep Portland Weird mural on our way back.

The city was easily walkable and had some nice spots. I know one of the things people had talked about when I mentioned this trip was the homelessness in Portland, but it didn't seem much worse than other US cities to me (and definitely nowhere near San Francisco). There was only one park we avoided that felt a little sketch, otherwise no issues.

Walking back to the hotel, we passed a food truck park, and there was a double-decker bus at the curb with a bar inside called Rachel & Rose Public Drinkery. We had to check that out, so we went in for a beer, and they also had a photobooth area in the driver seat where you could pose with Harry Potter props (which was the theme of the interior decor).

After taking pictures, we went up to the open-air top deck to drink.

In the evening, we stopped at Never Coffee, which had really odd flavors, something I usually love, but unfortunately, I didn't think my coffee was great. We did go with iced, so maybe they're better hot.

We hit up Deschutes Brewing for IPA flights, then came back to Crystal Palace. I'd bundled our room with a nightcap credit that could be used at the bar, so we spent that day's on dinner which we ate on the patio. Food was decent but not very memorable.

Our flight had been very early, so I was not opposed to going up to the room at 8 PM to call it a night. For a first day, we fit in plenty.

Day 2

Portland - Washington Park and night out in East Portland

Getting a good rest meant we were up and ready to go by 8 AM. We started off at Stumptown Roasters where I got their Other Mother latte, which was my second black sesame latte of the trip (this one with salt and pepper), and holy shit. Who knew black sesame lattes would be amazing? Still impatiently awaiting this trend moving east.

Afterwards, we got food at Screen Door, which drew me in with its Southern menu. A spicy bloody mary, cheddar grits, and fried green tomato eggs benedict is basically my ideal breakfast.

Our entire day from there on was spent at Washington Park. It was about a twenty minute walk just to get there from our hotel, then we hiked across the whole thing for about four hours, mostly uphill and in 98 degree temps by the time we finished. Absolutely exhausting, but also worth it.

First up was the Rose Test Garden, full of many pretty roses and a cute little gift shop.

Next was the Japanese Garden, which charges for entry. It had two different zen sand gardens, a corner pond where this very cute squirrel hopping across the rocks drew in a captive audience, another pond with bridge, and a waterfall next to a stream where a staff member was feeding the koi.

After that, we walked a winding path uphill to the redwood observation deck which was kind of a hike, but we got to see the very tall redwoods there...

...then we kept going over a bridge that crossed a main road and up a very steep hill to Pittock Mansion. We didn't go in (and couldn't even if we wanted to because it had closed early due to the heat), but from the outside it was still fancy. The real draw for us was the viewpoint out back which looks over the whole city.

We were so drained by now (especially me) that we ordered an uber to go get ice cream at Salt and Straw, and this is, like, easily top 5 ice creams I've ever had. I wish I could have tried all the flavors! I sampled an olive oil and it actually was tasty? For my two scoops, I had cinnamon snickerdoodle (real snickerdoodle chunks in it) and salted malted chocolate chip cookie dough, both of which were just wow. And I tried Mat's flavors - chocolate gooey brownie and peanut butter brittle caramel fudge - which were also wow.

That gave us the energy to make the (thankfully flat) walk back to our hotel after and get changed for the evening. We took a cab across the river to check out some things in East Portland, starting with Rogue Brewing. I wasn't really impressed with any of the beers, but the staff was so nice and gave us both a free taster of the day when we got in.

Our other plans were dinner and this goth club I wanted to check out, but the club didn't open until 8, so we had a lot of time to kill and weren't ready to eat yet. I opened Google Maps and saw an interactive place called Hopscotch nearby, and we both were excited about that so walked over. It was only $20 entry and very worth it! There were about a dozen rooms each with a different theme, and a bar at the front where I got an adult Capri Sun (alcoholic and came in a plastic pouch).

My favorite rooms were definitely the giant trampoline where your movement made colored lights fly across the walls and floor...

...the dancing room where the screen would layer your videos on top of each other for a cool trippy effect (unfortunately, I only have videos there so I'm giving you a completely unrelated photo)...

...and the giant glow in the dark ball pit.

It was all a big playground, and we had a ton of fun. We were ready to eat by the time we left, so we headed to Obon Shokudo for dinner. The menu was all vegetarian, and we ordered the same thing - giant tater tots (filled with mashed potato!) and tempura udon that was amaaazing! Definitely one of the best meals of the trip.

It was after 8 by the time we finished, so the Coffin Club was open, and I was in love the second I walked through the door. Foggy, red, green, and purple lighting, skeletons, black everything, and a literal seance happening in the back room. Perfection.

I tried a Winged Creature West Coast IPA from Wayfarer, a brewery down the street from them, and it might have been my favorite Oregon beer I had on the trip.

Unfortunately, back at Crystal Palace, I was told at 10:02 PM that I was no longer able to use my nightcap credit since the bar had closed at 10. So that felt like wasted money, and I would definitely not recommend the bundle packages as a result.

At least we were able to end the night in the gorgeous basement soaking pool. Hot tub temperature. Loved.

Day 3

Columbia River Gorge

We took a walk across town Friday morning to find a highly-recommended donut shop, Blue Star Donuts, that was near a gigantic high school. Damn, these lived up to the hype though. Their classic buttermilk donuts - we tried lemon poppyseed and raspberry - were incredible. We stopped at Super Joy Roasters on the walk back for coffees, then we checked out of Crystal Palace and took the train to the airport so we could pick up a Hertz car for the rest of the trip.

Once we had wheels, we were on our way to the Columbia River Gorge, making Mcmenamin's Edgefield our first stop. This was much more of a whole-ass complex than Crystal Palace. There were multiple buildings, they host concerts, there were bars and restaurants and a spa and soaking pool onsite.

We walked through the main hotel which felt like a school, then outside to find the winery which was in a cellar area. We shared a tasting to pick one we liked (got the pinot gris) and also ended up getting these giant cans of takeaway cider.

After that, we were off to see the waterfalls! The first one was Bridalveil Falls which was a little hike down a hill and took us to a small platform to see the two-tiered waterfall.

Mat insisted I pose with the cougar sign.

Next was Wahkeena Falls which wasn't much to see from the road - it started way too high up and was so long that we only got obscured views of the bottom, but it did send over a nice breeze.

Multnomah Falls, the famous one, was just down the road from there, but they were trying to charge $20 for parking! We turned right around and parked back at Wahkeena (for free), then took the 10ish minute hike on a hill beside the road to get to Multnomah. This was definitely the most built up one we went to with a whole visitor center and restaurant next to it. It was so picturesque with the waterfall flowing down under the bridge. Every photo I took looked like a professional shot; it just was gorgeous.

Our last stop was Horsetail Falls, and this one I liked because you could walk into the water below it (one guy was fully swimming underneath).

We backtracked a minute then and visited Oneonta Gorge which had a wooden tunnel built into the cliff, although the gorge itself is closed off.

Finally we headed to Cascade Locks, where we stopped to take pictures of the Bridge of the Gods (which crosses to Washington) and had dinner at Thunder Island Brewing on their upper floor patio with mountain views. The IPA I had was super good (plus it was called Secret Tunnel, and we love an Avatar reference) and so was my vegetarian chorizo taco bowl.

We took the long way to Estacada where our Air BnB was so that we could drive around Mt. Hood, although that was mostly obscured by the giant pine trees around it.

We made it to our Air BnB before sunset, and our hosts met us out in the parking area at the end of their driveway next to the guesthouse. They were both so nice and showed us all around the patio and guesthouse. Plus they brought their house cat out to meet us when we enthused about the calico we'd seen in the driveway coming in. Three cats total that hang on the property, as if I needed another reason to love it.

The guesthouse was gorgeous and so spacious. It was a separate farmhouse next to their fancy, glass-paned main house. The farmhouse decor was so cute and had so many nice touches, including a bottle of wine for us which made our trip to Mcmenamin's kind of redundant (oh nooo, we did an unnecessary wine tasting).

The yard was cute too. We had two chairs right outside our door that looked back at the field, and the patio with the hot tub was so adorably decorated with lawn ornaments. We put on our swimsuits and brought the wine out to the hot tub to drink it and chill.

Day 4

Willamette Valley, Pacific City, Tillamook, & Seaside

We had our coffee on the chairs outside and enjoyed a very leisurely morning getting ready. We didn't head out until 11 AM and also ran into the hosts' cat and a black cat outside, so we were off to a great start.

Our route to the coast was taking us through the Willamette Valley, which is wine country, so we stopped at a fancy winery for lunch near McMinnville called Willamette Valley Vineyards. They had a tiered back patio looking out over the grape fields, and we got a table right next to the fountain that flowed down under a bridge and into a bigger pond. So pretty. Split a bottle of "pinot noir" that was suspiciously rose colored, and I had a mushroom truffle bisque for lunch.

On our drive after, we also got our first Dutch Bros (regional chain) coffees. I had a cookie butter latte, and it was what Dunkin' could be if Dunkin' was actually good (Starbz for life). I also took advantage of passenger privileges by finishing off our leftover wine.

We stopped at Pacific City Beach and took a walk along the shore in the foggy weather (ok, this was the one day we did not have nonstop sun).

Next up was Tillamook Cheese Factory and Creamery, which I was hyped for, because cheese. It was huge and so crowded.

We went to order food right away and got a spot at one of the big communal tables. On the negative side, at 6 PM they announced the factory attractions were all closing (even though their closing time was listed as 7), which meant we missed the whole upstairs and samples. On the bright side, this meal was fucking great. I had the grilled cheese with fries and fire-roasted tomato soup with cheese curds, and Mat got himself a flight of ice cream and one scoop for me of the campfire s'mores. I was so happy with it that I wasn't even upset about the rest of the place closing.

It was going to be getting dark by the time we finished our drive, so we just headed straight for Seaside after that where we'd booked the Starry Night Inn for the evening. This place was adorable and basically felt like a cozy house both outside and inside.

The lobby had a bunch of free snacks and drinks and there was art all over the walls (bedrooms too) that was for sale. At the bottom of the stairs was a huge VHS selection, and there were board games and books to borrow.

We opted to stay in for the night and read books down in the empty lobby while we drank one of our gargantuan cans of pear cider in pretty colored opaque glass teacups. Very cute.

Day 5

Cannon Beach & Astoria

Breakfast Sunday morning was at the Chalkboard Cafe on a boardwalk, and we ate outside by the water. The breakfast bagels were made from homemade soda bread, so that was killer.

We were right by the carousel mall, which is a tiny shopping center with a carousel at the center, so we visited that before heading back to check out of the inn, then parked by the ocean to take a walk as far as the Seaside sign and Lewis and Clark statue. Excitingly, there was also some kind of dachschund convention going on by the aquarium, so there were many tiny dog sightings.

The famous Cannon Beach was next, and it really was beautiful. The tide was low enough that we could have walked to the gigantic rock in the water.

We had the sunniest weather, so we found a log to sit against where I enjoyed (slash choked down) my other impractically large can of cider and earned a slight sunburn in the time it took me to drink.

Before we left, we popped into Pelican Brewing for a beer, then we drove up to Astoria, our last destination of the trip, which was a quaint and completely walkable little town.

I'd booked us this boutique hotel called Near the Pier, and our attic room was freaking adorable. Total grandma vibes. Turquoise carpeting, flowered bedspread, lace tablecloths and curtains, even a stained glass along the stairwell like my actual grandma had in her house. I loved it so much.

The lobby had the same old vibe but with red carpeting, and again there was no reception desk, just self check-in.

We went for a walk after leaving our things, starting with the Pigeon Steps.

Our dinner choice was the Inferno Lounge, right on the water, and although the inside was nice with big red booths and decor, we went down to the glass enclosed sunroom area that looked at the ocean.

On our walk back, we saw this Garden of Surging Waves Chinese monument, then dropped off our leftover food and headed to Fort George Brewing, which had really excellent beers. There were two separate buildings, one of which had a live singer, and an outdoor patio in between.

We ended the night at a gay bar called Xanadu where I partook in karaoke night, and the super nice bartender gave me a sightseeing list which we ended up using the next day.

I drew myself a bath back at the inn and had a glass of wine, which was nice until I realized that I was extremely drunk and had given myself a stupid hangover to look forward to the next day.

Day 6

Astoria to Portland

We waited until exactly 11 to get our stuff together for checkout, because I was feeling rough even though we both had a really long night's sleep on the very comfortable bed.

The Coffee Girl cafe on the pier aided my healing process, as did the Powerade I picked up from the gas station, and I was also cheered by the many loud sea lions we could see out on their landing in the middle of the water.

We drove to the Astoria Column next. The gift shop sells wooden airplanes that you can take up the 164 spiral stairs to the top and throw off the edge. Mat's caught a drift and soared beautifully around the whole column, while mine immediately tanked into a nosedive for the ground.

Our next two stops were courtesy of our Xanadu bartender's list - the Peter Iredale wreck on the coast...

...and Youngs River Falls, which we had all to ourselves.

Mat wanted to cross over to Washington, so we took the bridge and tried to go to some sights and state parks there, but literally all of them we drove to required a fee, which was not worth paying since we only wanted to hop in for a quick look. I'm not counting this as a proper trip to Washington, and the state will remain unscratched on my scratch-off map.

We got another coffee in Astoria at Sleeper Cafe before making the two hour drive back to Portland, and our last dinner was at Steeplejack Brewing in a building with total church vibes. We split some mashed potato croquettes, and I had the vegetarian jerk tacos for dinner which were delicious, although I kept my beer to a 5 oz taster glass in deference to my morning of agony.

We made a final stop at Mcmennamin's Kennedy School near the airport to bring our Mcmennamin's count to three for the trip. This one really was in an old school, and all the rooms and bars had appropriate names (like Detention). The only bar open on a Monday night was the Boiler Room, but that was pretty neat with two stories and pipes as the railing and balconies. I had a non-alcoholic lemonade and Mat had an apple cider, then we went to the airport to return the car and catch our red-eye home.

It was a great trip overall, everything flowed so smoothly, and I must again commend our absolutely perfect weather.

There's so much more of the coast down south that we didn't get to see, as well as parks all over the state, but six days was a great sampler trip. Will be back for more someday, PNW!