There’s a fascination with Portland that seems to have spread globally. My first time in Tokyo in 2015, I came across a Portland festival. I decided I should visit Portlandia someday soon and see what all the fuss is about. I spent two days with my dear friend Lam hanging out in downtown in January. Here’s a sampling of what I found.

Portland was unfortunately having a cold snap of 32 degrees in January which limited my sightseeing. The locals said to come back in September for the best weather and that the best sights are the hiking trails, waterfalls and mountains. But I was looking for the hipster Portlandia that has now become so famous or infamous, depending on who you ask. This requires a trek into urban areas.

Portland is a city of rivers, bridges and neighborhoods of converted warehouses and brick buildings, at moments bleak, but on closer look, filled with a palpable creative energy. I would like to come back and explore more of the neighborhoods across the river, some of which have cute Craftsman houses, but I spent both days in downtown Portland.

You have to love a city whose number one attraction is the country’s largest bookstore! One of the city’s biggest attractions – Powell’s City of Books, which takes up a whole block and has its own parking garage, kept me glued to downtown. At first entry I felt overwhelmed by how big the store is, but then quickly realized how organized it was. It was easy to find what I was looking for, the staff was accessible and knowledgeable. I spent at least four hours here and left with a bag of books, some which were new titles at half off. They have a nice cafe where you can check out the locals as well as the books while grabbing a cup of coffee. Bookstores seems to wrangle an interesting set of characters. Someone told me that Powell’s Books was one of the best and kindest places to ditch a date. I can see how that might be true. I spent two days at Powell’s getting lost alone.

Close to the bookstore are some great restaurants, cafes and boutiques. I had hoped to explore further afield, but Powell’s kept me too enthralled. Here were some of the local highlights:

The Roxy Cafe – open 24 hours, a gay friendly, punk rock diner. On the walls are some oddities like a giant crucifix, t-shirts for sale that say “Gay Fu**ing Pride” amongst other interesting fixtures. Even the names on the menu items have an attitude. An establishment that is definitely “keeping Portland weird” as the rest of the Pearl District around it starts to look like a shopping mall. 

Stumptown Coffee Roasters – there are many hipster coffee establishments to be found everywhere these days but boy, they really do make a delicious cup of coffee. Expect to wait for a personally crafted cup of coffee. Minimal decor but a similarity with the Japanese Kissa lounges – they play vinyl records and exhibit the record cover on display. Bonus! While I was hanging out, they switched to play both sides of a Lionel Richie album from the 80’s. Couldn’t help but giggle a little. 

MadeHere PDX – a boutique that showcases various tables of locally made crafts from clothing, accessories, body care, stationary, jewelry to food, etc. A one-stop, local sampling in case you’re short on time and want a cool gift to bring home. 

North of West – clothing and home goods, unique, hand made, silk screened prints with a modern, aesthetic. 

Blue Hour – upscale restaurant in the Pearl District. Lovely setting with high ceilings, candles and a long bar. Warm atmosphere. Listed as an old staple front runner for the foodie culture wars.

Departure Restaurant and Lounge – swanky, modern rooftop location. Feels like you’re in the inside of a high class jet. Request a table with a view of the city. Asian fusion goes a little too hard on the spice and complex flavors for me personally, but you may like it if you like heat. Nice ambiance for a cocktail or a date in the lounge. 

Next time I come to Portland I’ll check out more neighborhoods across the river, hope to see the Japanese Gardens and some of the waterfalls and nature trails. Enjoy!