The Pacific Northwest is unlike any other part of the U.S. Oregon in particular, has some of the most striking nature around. The forests, lakes, mountains and overall greenery coupled with the popular hipster town of Portland bring a unique feel to this West Coast state. It's lovely to simply drive around. The coast is different from inland and there is a little something for everyone. It is also in close proximity to California and Washington state as well as Canada, notably British Columbia.

My Favorites

1. Portland

Columbia River Gorge

Highlights: Food, music, nature, hipsters
Suggest Staying: 3-5 days
Stay Around: Downtown or East Side (Jupiter Hotel)
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My third favorite city in the U.S., Portland is one of those awesome hipster cities that has exploded in growth over the past few years. It bears resemblance to cities like nearby Seattle, San Francisco, and Austin. Some of the awesome highlights for me were the music scene, food scene, and surrounding nature. People are super friendly and it’s interesting to see the diversity in neighborhoods throughout the city as it expands and changes. Portland is one of those cities where you can just be yourself. There are tons of outdoor activities within, and just outside, the city. Really the only thing that keeps me from moving there is the weather, being dreary for about 9 months out of the year like Seattle. That said, summer/fall is gorgeous. The best saying I heard while visiting, “Portland, where young people go to retire.” I think the TV series Portlandia seems pretty accurate in its depictions. For anyone interested in tiny house living, Portland, and other parts of Oregon, make it a solid choice as the state seems pretty tolerant of the lifestyle.

See & Do

  • Pearl District. Popular, trendy shopping district.
  • Division St. Hipster neighborhood on the east side.
  • Hawthorne. Hipster neighborhood on the east side.
  • Bellmont. Hipster neighborhood on the east side.
  • Alberta Arts District. Arts and music.
  • Mississippi Ave. Area for live music.
  • Powell’s Books. A staple known not only in Portland but around the country.
  • Mount Tabor Park. Spend a leisurely afternoon at the park.
  • Japanese Garden. Who doesn’t love a Japanese Garden.
  • Rose Garden. It’s nice, easily added to your itinerary of nearby things and earn some points with your girlfriend/wife.
  • Columbia River Gorge. Beautiful nature area for hiking.
  • Evergreen Aviation & Space Museum. What a find, this hosts the world’s largest aircraft, the Spruce Goose, an SR-71 spy plane, fighter jets, and a host of other cool stuff. Less than an hour from the city.

Food & Drink

  • The Observatory. Wonderful food with interesting, creative dishes.
  • Mojo Crepes. Crepes and bubble tea.
  • Juniors Cafe. Hip, funky, vegetarian and vegan options. It was here I ended up having breakfast with a Swedish fellow who introduced me to the concept of tiny houses, though at the time I had no idea what he was talking about.

Music & Nightlife

  • Mississippi Studios. Well known live music venue. I got to see The Next Waltz, a tribute to The Last Waltz which was The Band’s farewell concert, a collection of local musicians who join the main band as guests. Great musicians and all around great music at a super cool venue. Though it hadn’t been done before when I saw it, I believe this is now a regular concert fundraiser.
  • Alberta Rose Theater. Fortuitously happened that Eilen Jewell was playing during my visit. Outstanding singer, songwriter.
  • Bar Bar. Right on Mississippi Ave.


  • Jupiter Hotel. I had read about this cool, chic, hipster hotel and decided to spend a night or two. Was great, but ultimately moved to an AirBnB to save some money (though it’s not super expensive or anything). Definitely worth checking out. Be aware it’s pretty social and also next to a music venue. Which can be cool if you’re in the mood or not so cool if there’s a lot of noise, like on a weekend. I don’t remember having any issues, but I think I stayed during the week. Just take note.
  • Weather. Beautiful June-Sept, dreary otherwise. Temperature always seem to be relatively mild and I don’t believe it ever snows (at least if it does it’s rare and probably doesn’t stick around).

2. Columbia River Gorge

Eagle Creek Trail

Highlights: Mountains, rivers, forests, hiking, waterfalls
Suggest Staying: 1-3 days
Stay Around: Portland
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Basically part of Portland, I call this place out simply because of how awesome it is. There are many hiking trails and even a couple different driving routes (highway as well as scenic byway). I didn’t get a chance to explore much, but what I saw was impressive.

See & Do

  • Eagle Creek Trail. Upon the recommendation of my host, I only had one day/trail to do and this was along the river and ended with a waterfall and swimming area.


  • Driving. Take the byway either on your way there or on your way back from Portland (or both) if you’re not in a hurry and want to drive the old road with more scenery and waterfalls along the way.

3. Crater Lake National Park

Crater Lake

Highlights: Lake
Suggest Staying: 1/2 day
Stay Around: Portland, Bend, or Camping
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Gorgeous. Though not much to do here, the lake itself is breathtaking person and a great stop on your route north or south. I heard you can take a boat to the little island in the lake, but otherwise you pretty much just go to site, take in the view, snap a photo, and be on your way. Bring a jacket, I remember it being cool and/or windy.

4. Cannon Beach & Astoria

Cannon Beach

Highlights: Beach, The Goonies, Kindergarten Cop
Suggest Staying: 1/2 day
Stay Around: Portland (or Seattle)
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If you’re not in the know, Cannon Beach is where they filmed the scene in The Goonies where they use the skull key to find the cabin leading to the “rich stuff” and ultimately have an encounter with the Fratellis. If you have no idea what I’m talking about, watch the movie! If you are a fellow lover of the childhood favorite, you will have lit up by now realizing yes this place exists and yes you can visit it! Not only is there the beach, which is generally beautiful, the town of Astoria features the famous house as well as the jail. Not only that, but literally down the street is where they filmed Kindergarten Cop with Arnold Schwarzenegger at Astoria Elementary. Another childhood classic. Down by the harbor just around the corner is a lineup of sea lions, barking and lying on the docks lazily which makes for some fun. While pretty close to Portland, I actually took a day trip here on a previous trip from Seattle just for the day. For the child in me, it was a great day.

See & Do

  • Cannon Beach. Go for a walk, a picnic, a swim.
  • Astoria. Not much in the town other than being known for the movies.
  • The Goonies house. Someone actually lives hear last I heard, so don’t be obnoxious, but do revel.
  • The Goonies prison. Don’t be staying overnight :)
  • Astoria Elementary school. Sadly times have changed and it’s weird for adults to just be roaming around an elementary school, but you can at least snap a photo.

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