A Weekend in Portland, Oregon

Portland skyline

While my new home of Washington, D.C. was digging out of a massive snowstorm a few weeks ago, I was on the other side of the country, running along the rainy waterfront in Portland, Oregon. My trip to Portland was originally mostly business, but due to the impending storm, I moved my flight up a day to make sure I made it out there, which left me with two and a half days to explore.

I pictured Portland being a lot like Seattle – a city that I have really enjoyed in the past, both for its aesthetics and its overall vibe. My first impression was strong; within minutes of landing, I was on the light rail train headed toward downtown. It was one of my easiest arrivals in a new city that I can remember. After checking into my hotel, I headed out for some food and was pleasantly surprised to discover a 100% gluten-free restaurant just blocks away. At Petunia’s, I got a delicious (if slightly too small for the price) grilled cheese sandwich on gluten-free bread, together with a local cider. It was a great start to the weekend.


Struggling with jet lag after my coast to coast flights (DC to Phoenix to Portland, taking nine hours!!), I stopped in to Powell’s Books (one of the largest book stores I have ever seen) but only lasted about half an hour before succumbing to fatigue and returning to my hotel for a nap.


I woke up Saturday morning to cloudy skies and a light drizzle, but threw on my running shoes anyway and headed to the waterfront. A woman at the front desk had told me that I could run a 3.2 mile loop from the hotel to the waterfront and across to the other side of the river and back. I needed to get in eight miles for my half marathon training, so I ended up running the loop just short of three times, walking the rest of the way back. Despite the rain, it was a pleasant run along the Willamette River. On the far side, the path was more of a metal boardwalk floating on the side of the river, but it provided a nice view of Portland’s downtown skyline (which I went back to see the next day when the sun came out).

Portland waterfront

With it raining most of the day, I sought out something indoors to check out and the best (only?) option was the Oregon Historical Society Museum. I spent about an hour going through the two floors of exhibits that covered everything from the early Oregon Trail to modern day politics. And then I was kind of stuck as to what to do next. Luckily, my friend Erica had introduced me to a friend of hers who lived in Portland and he texted just in the nick of time about meeting up for a drink. To my surprise, we had to try several bars before we found one with any open seats – and it was only 4 p.m.!

Sunday started off on a high note as I woke up to sunshine and returned to the waterfront to take the pictures I had wanted to take the previous day. But as I checked out a gluten-free food truck for lunch, the skies clouded over and the rain started up once again. I couldn’t come up with anything else to do inside and didn’t feel like wandering around in the rain, so I went back and relaxed at the hotel.

Portland skyline and ducks

Portland skyline and boat

That evening, I took a tour of Portland’s underground, known as the “Shanghai Tunnels Tour.” From what I can tell, the whole idea of the so-called “Shanghai Tunnels” is a bit controversial. While the tunnels once connected the basements of many of downtown Portland’s hotels and bars, the tour was focused on the idea that they were used for a nefarious purpose: the practice of “Shanghai-ing.” This was a new term to me, but it apparently is used to refer to the practice of kidnapping people to serve as sailors in the mid-19th century. According to our somewhat obnoxious guide, they did this in Portland through the use of trap doors in bars that would open up and drop drunk patrons into the tunnels.

Shanghai Tunnels

We spent a good hour in the tunnels, although we didn’t go far – I doubt we made it more than a block. The guide (who was seriously one of the most annoying guides I have ever encountered) threw out all sorts of random “facts” about Shanghai-ing and told several tales of ghosts haunting the tunnels as well. It was certainly interesting, although I question whether almost anything she told us was actually true.

Shanghai Tunnels

The sun finally came out and stayed out the next day, but alas, I had to spend the day in business meetings. By that time, though, I was ready to move on to Seattle for the second half of my trip. Overall, Portland was a bit of a disappointment. It lacked the visual appeal and atmosphere of Seattle, the downtown seemed to be overrun with homeless people and there was little of interest to see or do in the city itself. Indeed, when I asked on Facebook for suggestions of things to see or do, almost all of the responses directed me outside of Portland itself, to the coast or into the mountains. If I ever head back to Portland, it would likely only be to use it as a base from which to explore the surrounding area.

Have you been to Portland? What did you think?

3 thoughts on “A Weekend in Portland, Oregon”

  1. I’ve lived in Portland for a few years now and when a friend came to visit on a particularly rainy weekend in January, I was also stumped on what to do. I agree though — if you can make it out to the Columbia River Gorge or the coast that would be ideal. Portland itself doesn’t have many touristy type of things to do. We have a great beer scene (gluten free beers too!) and food scene including restaurants and trucks alike. But of course there is only so much one can eat in a day. And if you ever are able to come during the summer, that’s when the PNW is really at its best.

  2. i love the pacific northwest; the entire outdoorsy vibe combined with the excellent food. IMO, vancouver takes the cake (lived there part time for a long while), while seattle is quite far back and portland behind.

    think portland with a car is a much more enjoyable experience. i’ve never been there w/o one. the japanese garden is nice (if pricey), the rose garden worthwhile (but not in winter). forest park is great for a walk in the mist. great veggie restaurants (again, not all right downtown). the other stuff is out of town.

  3. I live in Seattle and have been to Portland many times. Let me tell you as a local – they’re not the same :). They’re both waterfronts but Seattle is a little more mainstream 🙂

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