After Spending Four Days in Portland, I Finally Understand Why People Love It So Much (and Want to Move There)

After taking a two trains more than 3,000 miles across the country, going from Washington, DC (on a Sunday) through Maryland, Pennsylvania, Ohio, Indiana, Illinois, Wisconsin, Minnesota, North Dakota, Montana, Idaho, Washington, and Oregon, we made it to Portland, Oregon (on Wednesday). It was the most popular city in a state we hadn’t visited before, so we were excited to see what it had to offer.

After all, people had been talking about how incredible Portland was, and that was in addition to the fact that a famous comedian made a show called Portlandia in which he and his co-star basically mock Portlanders for everything they’re worth.

In the lead up to the trip, people told us how amazing Portland was, including a woman at my yoga studio who has a tattoo of a famous bridge in Portland that spans her entire back. I had never felt that close to a city…or anything in life…to get it tattooed on my body, so this place must be pretty cool if she did. Our original plan was to spend three days in Portland—Wednesday, Thursday, and Friday—before heading back on a redeye flight on Friday night into Saturday morning, so we had to milk the city for what it was worth in a short time.

As we walked to our hotel from the train station, we noticed there were plenty of people going through hard times. As we walked by them, none of them said anything to us, which was quite eerie. In DC, we were used to being harassed by bums who asked us for money incessantly and, on many occasions, called us racial and homophobic slurs when we disregarded their begs. But these bums were different. They didn’t ask for anything, didn’t bother us, and didn’t talk to us, and it was the first of five incredible things I noticed about the city. Portland bums were quite nice. They minded their business, took what people gave them, and didn’t harass anyone. It was a welcome change from the District.

As we arrived at our hotel, we spoke with the concierge, who told us about all of the things we could do in the city. And that’s when I realized the second incredible thing about Portland: there are so many fun things to do. We had our choices between natural attractions like the Japanese Gardens, Rose Test Garden, Pittock Mansion, the Riverwalk, aerial tram, and others, while balancing that with the urban experiences of the restaurants, breweries, museums, and markets. And that was just the city. There were surrounding areas like the Columbia River Gorge, Mount Hood, Mount Saint Helen’s, and the Pacific coast, which was less than a two-hour drive away. We assessed our options and decided that we would spend two days in the city, then check out of our hotel on Friday morning and head to the airport, where we would rent a car and drive to the coast, spending the day on the beach. Then, we’d drive back to the airport, drop off the car and fly home on our redeye flight.

Our first adventure was walking to the western heights of Portland, which featured the Rose Test Garden, Japanese Gardens, and various monuments and dedications to Portlanders and its native inhabitants. On the way we stopped at Powell’s City of Books, the famous bookstore in Portland and took the mandatory selfie. Further along our way, we ate lunch a great burger joint called the Idaho Fry Company, with a cashier and cook who were extremely nice and served us well.

About 30 minutes later, we arrived at the gardens, where we walked through several trails, seeing different monuments to both Lewis and Clark and Native Americans, as well as a stunningly dark, yet beautifully done monument dedicated to remembering Holocaust victims.

Another 20-minute walk brought us to the Rose Test Garden, which featured no roses, as they weren’t yet in season to bloom. But a quick walk up more steps took us to the Japanese Garden, which features an incredible array of six different Japanese-style gardens in what would be their natural habitat in Japan. The gardens are surrounded by massive Douglas Fir trees that seem to be at least 100 feet in the air.

After our excursion into nature, we walked back to the city taking a break in the hotel before having dinner at a local restaurant called Huber’s. After dinner, we rushed back to our hotel, as we were excited to sleep in a real bed, having slept on a train the last three nights. We fell asleep watching Forensic Files as we usually did when staying in a hotel.

The next day, we dedicated our time to the attractions of downtown Portland. We first walked to the Oregon Historical Society, which provided a well-balanced view of Oregon’s history, including its persecution of Native American peoples and its banning of African-Americans from living in Oregon until the early 1900s. While Oregon, and Portland in particular, seems to be an open and welcoming place, it wasn’t always the case, so it was nice to see the curators of the historical society provide that perspective.

After a quick lunch, we hopped on the Portland Streetcar and looped from the west to east side of the city, stopping off on Taylor St, and walked one block to a local game store called Guardian Games.

It didn’t look like much on the outside, but on the inside it was much different. It was most incredible game store I had ever seen, easily 20,000 square feet of all kinds of games: board games, card games, collectible games, tabletop games, dice games, and more. Abby and I both enjoy playing board and card games (perhaps me a bit more than her) so this was like a mecca beyond belief. It was also no surprise that the store stocked a dice game I’d been seeking for some time, so I purchased it along with a few packs of collectible cards.

After that, we walked across one of Portland’s many bridges back to the west side of the river and strolled along the Riverwalk as dusk started to settle. We made a quick stop at our hotel room to drop off our purchases from the day before going to dinner at Jake’s Crawfish, a popular seafood restaurant in Portland, owned by McCormick of McCormick and Schmick’s steakhouses. I’m not a foodie, but I’ll say that my dinner was the best piece of fish I’d ever had.

Friday morning, which began our third day in Portland, we continued our plan and took the Tri-Met MAX light-rail line to the airport, where we would get our rental car. Around 11 a.m., now riding in a Nissan Sentra, we hit the road north through Vancouver, Washington before crossing the Columbia River again on to US-33. Our destination was Astoria, Oregon, the location where Disney filmed the movie The Goonies. While in the car, I came to my third realization about Portland (and Oregon, in general): it has incredible natural beauty. While this is certainly not a surprise, it is only realizing when you’re in the middle of it. Our car ride took us along the Columbia River, then through dense Douglas Fir tree forests, and eventually along a beautiful coast.

As we made our way through Astoria (pronounced ÆS-tohr-ia, not æs-TOHR-ia, as I thought) hoping to find a nice beach, we took a diversion to stop and take a picture in front of the Goonies house. Unfortunately, our plan was foiled by a rudimentary sign that indicated that the police would be called if you came too close to the private property. So we took a picture from an area that wasn’t private property.

After taking our quick selfie, we realized that Astoria wasn’t much, and didn’t offer us the beach we were looking for, so we turned south and kept driving to a place called Seaside. When we pulled into the town, we realized it was exactly what we sought: a quaint beach town along the Pacific Ocean. We found street parking and walked along the main street, seeing everything we expected of a typical beach town: ice cream shops, a massive arcade, beach clothing stores, and even an old-time photo place.

We were sure to stop in the arcade and play skee-ball, until we were deterred from our usual game by something we found that was much better: bingo ball. In a room in the middle of the arcade, we saw two lines of 30 tabletop machines, with a caller sitting on a podium in the middle of the room. People were rolling balls down the table as quickly as they could. What is this place? Whatever it was, it looked incredible. About a dozen people were playing, and I quickly realized what the game was about: Get five in a row… a bingo. The game only cost 25 cents, and was one of three in the world, according to the caller. I came from a bingo family, so Abby and I immediately sat down and played, and kept playing, until our desire for the beach and sand overtook us.

As we walked outside and headed toward the beach, we could smell the salt in the air. It was one of my favorite aromas and always brought a smile to my face. A few hundred feet down the block, the road ended at an overlook perched on top of one of the widest beaches I’d ever seen. The beach wasn’t particularly long, but the ocean seemed like it was a mile away from us, and in the middle was a mixture of very fine black and white sand. We both smiled and I immediately ran down the stairs and onto the sand, running toward the water. I began to twirl as I raised my arms in the air, breathing in the salty mist. I loved it. I loved the beach. Abby loved the beach. And there we were, a quick two-hour drive from Portland, on the beach.

We stayed until it got late and became time to head back and catch our flight. We waved goodbye to the ocean, took in one last breath of salty air, and drove the two hours back to Portland, arriving at the airport around 7 p.m. for our 10:40 p.m. flight.

The problem was that the flight wasn’t going to happen. Shortly after arriving, we found out that our flight was delayed until 2 a.m. due to weather problems on the east coast. Our connection from Newark Liberty airport to Washington Reagan airport had been cancelled. We talked with an attendant at the United desk, who was extremely compassionate with our situation. We knew it wasn’t her fault and she was doing the best she could to find us a way to get home, but in the end, we settled on a direct flight on Sunday, which mean we would be staying in Portland for two more nights and one day.

Flexibility was Abby’s and my strong suit, so we took the MAX line back to downtown Portland and found a swanky hotel in the downtown area. After a quick dinner at MOD Pizza, we retired around 10 p.m.

Our experience with the United attendant, who lived in Portland for about 20 years, was the start of the fourth incredible thing I learned about Portland: the people are so damn nice. After checking in at our new hotel, a quick, friendly chat with the hotel attendant yielded us a free room upgrade to a corner room and two free coffee drinks in the morning. When we woke the next day and used the coupons to get the coffee drinks, the woman behind the counter gave us a free chocolate bar. Our experience in the Portland Saturday Market was just as good. Every vendor was cordial, proud of their work, and extremely friendly.

In the afternoon, we took an Uber to the Pittock Mansion to get a view of the famous home and its incredible overlook of Portland. Everyone sitting at the overlook was nice, engaging, and respectful of everyone’s opportunity for a good view.

Another great Uber driver dropped us off at The North Face store, where Abby and I planned to get new jackets, taking advantage of the lack of sales tax in Oregon. The assistants in the store were incredibly nice and helpful and I sensed no pushiness from any of them. While trying on different jackets, we spoke with a girl who had moved to Portland from San Francisco a year before, who talked about her love for the city. She told us about her experiences and how much better she liked it than California.

The people were just so damn nice!

Donning our new jackets, we walked around the corner and stopped at a brewpub for an afternoon snack. The bartenders were very nice, the complete opposite from many bartenders in DC who maintain a strong arrogance. They talked with us, explained their beer and food menus, and asked us where we were from and asked how we liked Portland. When one of them saw that I had put the Washington Capitals game on my phone and leaned it against a ketchup bottle, one of them, without my asking, put it on one of the few big screen televisions in the bar. There we were, in Portland, Oregon, and one of the local bartenders just put up a hockey game from two teams from the east coast. The server for our dinner that evening was very nice, as well, and provided us great service for our last meal in Portland.

Again, the people were just so damn nice…

The next morning, we woke and took the MAX red line to the airport, which led me to the fifth incredible thing I realized about Portland: It has great public transportation infrastructure. Not only does every street seem to have a bike lane, but the streetcars and light rail system span far and wide and operate at useful hours. For example, to get to the airport on time, we needed to hop on the MAX red line by 6 a.m., and I was grateful to find that the train ran that early on a Sunday. Not only did it run at 6 a.m., it started at about 3:30 a.m. This is a far cry from the DC Metro system, which only starts operating at 7 a.m. on weekends. If we were in DC, we wouldn’t be able to take the Metro to the airport for an 8 a.m. flight on a Sunday. In Portland, it’s not a problem.

And those are the five incredible things about Portland (and probably Oregon, in general):

  1. Natural Beauty
  2. Lots of things to do
  3. Extremely cordial people
  4. Non-aggressive bums
  5. Adequate public transportation

After four days in Portland, I get why people love it so much. We did, and you probably will, too.

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