portland, oregon - 2017

Despite the fact that my first two blog posts are now centered around it, I find my own birthday to be very stressful. I try to keep celebrations mostly low-key to spare myself the crippling anxiety that accompanies party planning. Last year I ended up having a party at a dive bar in North Center with $2 beers and it turned out great! However, I still wanted to do something a little different for this year, with it being a bigger milestone, so my boyfriend Pete and I decided to head out of town. 

My requirements when choosing a destination were affordability, reasonably decent weather in October, and a good Halloween atmosphere. While I usually try to save on hotels, I did want to be able to stay somewhere a little nicer since it was a special occasion. New Orleans was my first idea, but it quickly got crossed off the list due to steep flight and hotel costs. Next I started planning for Key West, but Hurricane Irma derailed that plan too. Finally, I ended up settling on Portland - a location that had been on my list for a while, and had remained reasonably priced even with last minute traveling. It couldn't have been a better choice.

This is a long post - so if you're looking for something specific you can jump around with these handy buttons. 

Trip Highlights

Portland Japanese Garden 

This was by far my favorite thing we did (and honestly one of my favorite places I've been to, period). We got beyond lucky with the weather - it was in the 50s-60s for most of the weekend, and the day we went to the Japanese Garden was brilliantly sunny. Portland seems to be blessed with brilliant fall colors all over the whole city, but the trees here were so intense and colorful it almost seemed fake. I am too lazy to drag a good camera around with me these days but I wholeheartedly regret having only my iPhone with me that day.

Aside from the beautiful winding walking paths, there is also the Umami Café, where you can drink tea and eat Japanese snacks on a balcony overlooking the gardens. Pete and I both tried the sencha green tea which was very good. The food is very light, however, so I considered this more elevenses than a true meal.  There's also the Cultural Village, with a gift shop, some small exhibits of Japanese artwork and historical artifacts, and an explanation of the history of the Japanese Garden in Portland. 

I honestly would recommend a trip to Portland in the fall just to come here - but apparently it's much more common for there to be cold rain, so you might not get the absurdly magical sunlight we did. Still would be beautiful, though, and I'm sure it's also gorgeous in the spring.


Another very common Portland tourist stop is the Pittock Mansion, a turn of the century estate on the hills above the city. The weather was unfortunately the very opposite of the morning we spent in the Japanese Garden, so we couldn't really take in the spectacular views of the city from the hilltop. It did make for some appropriately spooky photos, though.

I love museums and I'm especially into historical recreations (one of my favorite parts of any museum in Chicago is Yesterday's Main Street in the Museum of Science & Industry). The house is decorated with period furniture, although sadly not many originals from the Pittock family themselves. One thing that surprised me was how awesome the bathrooms were - surprisingly modern with waterfall showerheads and white subway tile. I was disappointed to realize later I forgot to take a picture of them. 

It was really interesting to learn about the history of the Pittock family. Henry Pittock went from a penniless 17-year-old Oregon Trail pioneer to the founder of the modern-day Oregonian and one of the richest men in Portland. Unfortunately, his children weren't able to upkeep the massive house and it was sold just a few decades after it was finished. Luckily, the residents of Portland bought the mansion to save it from being torn down and replaced by a subdivision.

Go on a clear day to take advantage of the sweeping views of downtown Portland. We also heard from more than a few local residents that the mansion is decorated beautifully for Christmas every year. 

Biking along the river

Because the weather was so nice, we ended up spending a lot of time just exploring the city and trying not to think about the imminent Chicago winter. We stayed at a great spot right next to the river (more about our hotel a little further down), and they had an awesome program where you could rent out some bikes for the day. They include locks and helmets if you'd like - I absolutely require a helmet because I am clumsy and prone to falling off bikes. This was a great way for us to get around! The Willamette River has a beautiful waterfront park next to it with large paths perfect for biking, and it was a great place to take advantage of the time change by catching a sunrise. 

One afternoon we biked across one of the bridges and met a few friends to bike from bar to bar, which was so much fun I apparently forgot to take photos of most of it. Our last stop was Washington High School, which would have been weird except that it's not a high school anymore - it's been redeveloped after being vacant for many years. It's got a great roof deck and was the perfect spot to end an afternoon and enjoy a view of the city.


I didn't get a ton of photos at the hot spring, for reasons that will soon become apparent. Here's a picture of the Cougar Reservoir nearby instead.

I didn't get a ton of photos at the hot spring, for reasons that will soon become apparent. Here's a picture of the Cougar Reservoir nearby instead.

We had decided to take a few days off for this trip, so when Monday rolled around we decided to get out of the city a little bit. Unfortunately due to the fire in the Columbia Gorge earlier this year, some of the spots we had wanted to visit weren't open to the public yet. We rented a car, picked up our friend John and headed three hours outside Portland to Cougar Lake, located in the Willamette National Forest. 

The primary reason for this long scenic drive was that we had heard good things about the Cougar Hot Springs (also known as Terwilliger Hot Springs). If you look it up, you'll find awesome photos of beautiful scenic pools under a canopy of trees - looks straight out of Lord of the Rings or something. 

We went on a Monday, thinking it would be less busy than the weekend and that maybe we'd get lucky and have the pools all to ourselves like social media led us to believe. Upon arriving in the parking lot nearby, an attendant charged us $6 each and warned us that clothing was optional at the spring. Unfazed, we hiked a short way up to the pools, carrying our tiny hotel-issue towels with us. 

Let me say first that I don't think I'm a prude. While I prefer not to be naked in public, I'm certainly not shocked and appalled by other naked people. Years of swim team as a kid (and heading into the locker room to find an old lady sitting bare-cheeked on my towel) taught me that many older folks really have no problem being naked in front of other people. But I will admit I was not prepared for the Cougar Hot Springs.

First off, it was extremely crowded. There are five different pools that stair-step into one another, with the top pool pouring into the next level, and so on. Every single pool except for the very bottom one was nearly full when we got there - people were sitting shoulder to shoulder, essentially. And a better warning really would have been "clothing is discouraged" because almost every single person was naked as the day they were born. 

I know this sounds very precious and pearl-clutchy, but I balked for a second. I have some personal space issues and certainly didn't want to wedge myself into one of the crowded chatty circles, but I also didn't find the lowest (and coldest) pool, which looked like murky run-off from the crowds of naked hippies stewing in upper levels, particularly appealing. However, faced with the prospect of six hours cumulative driving for no good reason at all if I did not get in, I gritted my teeth and decided to go with the flow, like a twig on the shoulders of a mighty stream.

John took this photo, but I borrowed it to show you the layout of the pools and how busy it was. Check out more of his stuff on Instagram - @johncywinski

John took this photo, but I borrowed it to show you the layout of the pools and how busy it was. Check out more of his stuff on Instagram - @johncywinski


I wish I could say that it was an amazing, transcendent experience, buuuuut I never really relaxed enough to truly enjoy it. I did eventually work up the nerve to move to the upper pools, and I was able to take a few photos that capture how magical this place would be if you did manage to find yourself relatively alone there. I would not do this again, but all said and done I'm glad we did go - it makes for a good story, anyways.


Birthday breakfast at Mother's Bistro

Birthday breakfast at Mother's Bistro

We didn't spend a lot of time focused on where we were eating & drinking on this trip, but we managed to find some good spots anyways. Some of my favorites: 

  • McMenamin's Backstage Bar: Named because it's located in the back of an old 1920s movie theater, it's got massively tall ceilings and pool tables galore.

  • Mother's Bistro & Bar: We walked here for breakfast on my birthday - solid spot for breakfast and giant mimosas. I really appreciated their Halloween decorating efforts, too.

  • Basecamp Brewing: Very #Portland brewery with a nice patio outside their taproom.

  • Washington High School: Mentioned above - repurposed high school with a bar on the roof deck, overlooking the city.

  • Secret Society: A Victorian-era hall with live music, looks to be primarily jazz & swing based on their event calendar. We ended up here for Halloweekend and I kept expecting the Sanderson sisters to make an appearance.

  • Swift Lounge: Cocktail bar with a cool vibe; they serve seasonal drinks in giant mason jars for a surprisingly low price.

I will confess that I actually took this photo from the hotel website because I scribbled all over my photo of the room in Instagram stories. But I promise it looked just like this.

I will confess that I actually took this photo from the hotel website because I scribbled all over my photo of the room in Instagram stories. But I promise it looked just like this.

Where we stayed

Knowing that I'm a completely neurotic disaster when it comes to planning, Pete kindly took the reins once I made up my mind on a destination. He had stayed at the Kimpton Riverplace Hotel on a previous trip to Portland and loved it, and it ended up being a perfect spot for this trip. Situated on the river next to a beautiful waterfront park, it's also right in the middle of the city, which made it relatively easy to get to the tourist spots to the west and more trendy, fun nightlife to the east. I should take this opportunity to mention that working in the hotel industry has made me slightly picky about where I stay, and I really enjoyed this hotel. Good pick, Pete.  👍