Portland – quick travel guide

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Portland was and still is one America’s most (authentically) hipster, hip, trendy, coolest towns to live in.

It has the authentic Portland quirky weird vibe, beautiful pacific northwest landscapes and trees (which actually looks like real nature vs California’s desert landscape and beaches), beautiful craftsman homes in giant forest ambiance, and a vibe that feels very authentically white-American rather than the typical hispanic immigrant culture you’ll find in America’s other big cities.

For many years since 2010, it was one of the fastest growing cities and taking in the millennial exodus from burned-out overpriced cities like Los Angeles, San Francisco, and New York. The original Portlanders were all “F**K YOU, CALIFORNIANS! GO BACK TO WHERE YOU CAME FROM AND DON’T CALIFORNICATE OUR BELOVED PORTLAND!”

And rightly so…because all the outsiders were bringing in their money, buying up property, raising property values and rent beyond what local Portlanders could pay, clogging up streets with traffic, and just ruining the organic hippie ambiance.

Let’s find out why I (and everyone) think Portland is so cool.

Portland culture

I’m not a true Portlander, not from there or ever lived there, but visited it numerous times and considered it like my 2nd home during 2014-2019. So I guess you could say my view of Portland is somewhat of a savvy visitor. Let’s learn some things about Portland’s hipster culture…arguably among the most defining origins of American hipster culture.

Where to stay:

Portland is generally divided up into 5 areas…Southwest, Northwest, North, Northeast, and Southeast. As a visitor…the unique Portland vibe you’re looking for is the “weird Portland” (quirkier, eclectic, bohemian) which is primarily in the east side of Portland (northeast and southeast). It also happens to be the more affordable and bike-friendly part of Portland.

The west side of Portland feels more like any typical city…ranging from downtown area with big buildings, or very residential area. So I’d generally avoid it, especially for first-time visitors.

Specifically, I recommend the Buckman area. It’s on the east side of Portland but still centrally-located. And from here, you can easily drive to all districts of Portland within 15 minutes. And also be in walking distance of Hawthorne (my favorite street). If I had to pick a pinpoint, I’d aim for Hawthorne and 28th. But really…it doesn’t matter much if you have a car.

Authentic housing to stay in…

  • Friend’s house with a big back yard.
  • AirBnB – lots of cool spots on here. You can try craftsman home, tiny home (in the backyard of a craftsman home), old converted hotel.
  • For sure, I’d prefer craftsman home over a sterile modern apartment.

Main streets to explore:

Look up Salt & Straw ice cream shops, which are often located in Portland’s busiest areas, and walk those streets. There are many cuter smaller areas too, but I can’t remember names right now. I remember only when driving there.

  • SE Portland (creative, artistic, bohemian, weird)
    • Hawthorne Blvd – my favorite street, which goes from the water all the way to Mount Tabor. 12th to 26th street feels more downtown. The cool area starts from 26th, walk east from here.
    • Division St, Clinton – Division is a main street with a rustic woodsy vibe. The busier/better parts are from 10th to 60th, then again at 82nd where it becomes the Jade District. Clinton is the back street that runs parallel to Division. Lots of shops and eateries. I would also walk through Ladd’s Addition. Feels like a big neighborhood park with many beautiful craftsman homes.
    • 82nd Ave (Jade District) – where Division & 82th Ave meet. Also known as the “New Chinatown”. Lots of places to eat here and shop as well.
    • Mississippi Ave – from Skidmore down to Fremont. It’s ok. Plenty of food options but kinda dead at night. I much prefer Hawthorne or Jade District.
    • Lively night areas – Mississippi Ave & Williams/Mason/Skidmore. This is what my friend said but honestly it felt a little dead when I came off-season.
  • NE Portland (laidback)
    • Alberta St – another awesome street for shops, food, and a bit of Portland’s eclectic vibe. I’d walk 14th down to 30th, and then cut over to McMenamins Kennedy School. More of. a daytime street IMO. At night, can feel kind of dead when it’s not summer.
    • Broadway – another busy street.
  • NW Portland (metropolitan, downtown posh)
    • This area feels like any big city downtown area. Can be nice but I feel it’s a waste of time as you’re in Portland to see the more quirkier Portland things. If your walking tour takes you through here, I’d honestly skip it. If you’re looking for nightlife, the most consistent nightlife would be in this area.
    • NW 23rd Ave – a good street to explore the full range of NW Portland. Lots of shopping, food, cafes built into old houses.
    • Old Town – some cool shops and clothing boutiques. It’s right next to the Pearl District and often referenced together as one combined general area.
    • Pearl District – downtown area with downtown type of shops and eateries, bars and nightlife. I only go here if my friends are looking to party city-style. Or if I’m craving Voodoo Doughnut. 🙂
    • Nob Hill – posh area, expensive-looking, nice and pretty. Checkout the area around NW 23rd & Glisan. It’s the only tourist area I recommend on the west side of Portland.
    • NW 13th Ave – another notable street in this area.
  • SW Portland (residential, water area)
    • Even though it’s a nice area to be and also many spots to relax or do activities by the water, I almost never go here. And I don’t recommend it for tourists.

House tour:

  • Because no Portland tour is complete without exploring the beautiful craftsman homes of the pacific northwest of America.
  • Burnside St – many nice houses going west of SE 47th Ave, also drive around Laurelhurst Park area. Otherwise is boring.
  • Ladds Addition – a fancy neighborhood of big beautiful craftsman homes. Definitely walk around this area. It’s great for when you’re in the mood for a “walk in the park”.

Restaurants:

Portland’s restaurant scene is one of my proudest moments as an American. They got entire streets full of amazing food. Awesome restaurants back-to-back-to-back. You can literally jump on Google maps and find anything about 4.5 stars and it’ll likely be a total hit. But below are some ideas to give you the “food culture” of Portland.

  • Brunch/Lunch scene –
  • Dinner scene –
  • Food truck parks – you can’t go to Portland without eating at a food truck park. The food is amazing and there’s something for everyone. Best done in groups where everyone orders a different thing to the table. Some might also have movie projections, outdoor games, and other fun stuff going on. Look some up and visit one.
  • Salt & Straw – iconic ice cream chain originally from Portland. Visit any of their locations (usually located on popular Portland streets).
  • Voodoo Doughnut – iconic donuts chain from Portland. Fun picture-worthy designs.
  • Late night food:
    • Le Bistro Montage (closed) – I am sooooo incredibly sad this place closed because of COVID. It was the coolest late night spot ever. A restaurant in a big weird space right under the freeway. Dark and vibey, and good food (and interesting dishes too, like alligator). Now their cuisine lives on in the form of multiple food trucks throughout the city. But I miss the restaurant space. It was THE spot to be when you’re hungry at 2am and want to go somewhere cool.

Things to do:

  • Portland culture –
  • McMenamins Kennedy School – a very Portland culture thing. The McMenamins brothers were known to convert old historic buildings into other things. In this case, they turned an old grade school into a hotel and restaurant. Eat lunch here, and then walk the hallways. Get your camera ready for photos of weird Portland-ey stuff. There’s also the saltwater pools here, which are a popular thing for locals (throughout all seasons).
  • Nature:
    • Multnomah Falls – about 20 minutes drive away. You don’t have to do the hike if you don’t want to. You can walk up 10mins for easy pictures. On your way back to the city, you can pull over at Dalton Point to get a look of the water and nature landscapes on the other side of the Columbia River.
    • Mount Tabor – really nice park. Park at the visitor center and walk over to Reservoir #5 to get elevated views of the city. It’s not a huge park, so you can move through quickly.
    • Reservoir.
    • Goat’s ear plant – distinguishable by the white powdery aesthetic. Touch them and see…nice and soft.
  • Hopscotch Portland – interactive light art gallery.
  • Electric Castle Wonderland – nickel arcade. Kinda lame and I wouldn’t waste time here as an adult, but might be fun if you have kids.
  • Freakybuttrue Peculiarium Museum – look up pictures, read reviews, and decide if it’s for you.

Bars, clubs, and nightlife:

  • There many bars everywhere.
  • McMenaman’s – these brothers bought a whole bunch of different venues and turned them into really cool themed bars. Check some out when you get the chance.

Miscellaneous tips:

  • Quick travel tips for the United States.
  • Safety – generally people say all streets lower than 82nd Ave are safe, and higher than 82nd Ave are dangerous/sketchy. But you can feel the vibe for yourself. If it doesn’t feel right, don’t walk alone or don’t be there at night.

Itinerary:

  • DAY 1 – check out Hawthorne Blvd.
  • DAY 2 – checkout Division St. Get brunch or coffee nearby and then walk around Ladd’s Addition and then further
  • DAY 3 –

Nearby towns:

  • Seattle*
    • I like Portland more than Seattle. More of a unique vibe, more compact, more affordable, nicer people, closer relationship with nature. Feels like the city is built within a giant park. So walking around outside (almost anywhere in Portland) always feels like you’re walking through a park. It’s very peaceful and nature-y.
    • But no doubt, Seattle is also a great place to be with many things to do. Seattle’s uniqueness is more that it’s probably one of the best balanced places of city and nature in the US. If you want more city things to do and also more nature things to do, it feels like Seattle beats Portland in both. But if you want to feel like you’re living in nature, then Portland wins. Regardless, Seattle is beautiful and definitely worth a visit.
    • In terms of tourism IMO, Seattle has more tourist things to do but Portland has more unique tourist things to do. Between the do. Portland is a MUST-SEE for me and Seattle is a good place to live. With that said, some visitors might find Portland too quiet or boring compared to the bigger cities.
  • Ashland* – definitely a worthy stop if you’re driving up from California. Pass by the artsy area and then check out the Japanese garden. Even if you only have 30mins, it’s enough.

Unfiltered notes:

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