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, waterfalls, hot springs 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. Best time to visit is summer and fall which are absolutely gorgeous.

My Favorites

1. Portland

Columbia River Gorge

Highlights: Food, music, nature, hipsters
Suggest Staying: 3-5 days
Stay Around: Pearl District or East Side (Jupiter Hotel)
Internet: Strong
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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.
  • The Fair-haired Dumbbell. Quirky, artsy building. Looks like something a predecessor of Salvador Dali or Gaudi might create.

Food & Drink

  • Just Bob. Awesomely quirky breakfast spot.
  • Cafe Destino. Good breakfast spot.
  • 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.
  • New Seasons. Large healthy grocery store.
  • Spitz. Mediterranen food with a bar and outdoor seating.
  • Prost. German restaurant and beer garden.
  • Samurai Blue Sushi & Ramen. Not the best sushi I’ve had, but what an amazing fish selection.
  • Crisp Salads. Outstanding made to order salads.
  • Tao of Tea. One of my new favorite tea houses. Great tea selection, unique tasting experience, light food, exceptional staff, and one of the coolest, chillest spaces. The tea house is adjacent to the tea shop, both having different hours.
  • Smith Teamaker. Great spot for tea. You can sit, takeaway, or purchase in the shop. Go for the tea flight.
  • Tea Chai Te. Nice tea spot.
  • Fly Awake Tea House. Small unique alley way tea house.
  • Tov Coffee. Tea or coffee in a double decker European tour bus with Middle Eastern decor.
  • Kava Seia. Kava bar. Owners are a husband and wife duo that are superb people. The drinks plus experience is phenominal. Kava is a root crushed up into a drink that gives you a bit of a buzz, kind of like alcohol but without the hangover as it was described to me. Different mixes and elixirs will put you in a great mood. Also serve refreshing mocktails.
  • Khun Pics Bahn Thai. Thai restaurant that will make you feel like you’re in a jungle forest.
  • Kinboshi Ramen. Really good ramen. Also has a couple other restaurants that share the space.

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.


  • Columbia River Gorge. Absolutely gorgeous area along the river with endless waterfalls and hiking trails. There are two routes, the main highway as well as the scenic byway (more waterfalls). Two places of note, Eagle Creek Trail is a lovely waterfall hike to a swimming hole and the magnificent Multnomah Falls right off the highway. During peak season you need to reserve a time and it costs $5.
  • Hood River. Cool, hipster town right along the Columbia River Gorge with some cool shops and places to eat. Definitely worth an afternoon.
  • Vancouver (Washington). Actually located just over the border in Washington state, a lot of people from Portland are moving across the river to this little city. Nice, clean town only about 20-30 minutes from Portland. Dandelion Teahouse & Apothecary is a must stop if you like tea. Oh man, the jasmine blueberry tea is exceptional. The riverfront is quite nice.
  • Salem. The capitol city is more hipster than I would have thought, with some nice healthy restaurants like Taproot Lounge & Cafe and quirky shops. Not nearly as cool as Portland, but if you’re curious, it’s an easy couple hour excursion.
  • 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.


  • 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. Bend


Highlights: Mountains, rivers, forests, high desert, hiking, skiing, waterfalls
Suggest Staying: 3-5 days
Stay Around: The Grove
Internet: Good
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From traveling around the U.S., I’ve heard Bend mentioned quite a few times. Located out in the high desert, meaning high in altitude, sunny, and dry, it’s a very different climate from the dreary reputation of the Pacific Northwest. Several hours from the coast over the mountains and into the desert, the topography is just like that of Northern California. Between that and the overall vibe of the town, felt a lot like Boulder, Colorado. Bend is a healthy, friendly, outdoor mountain town. Great for nature, hiking, and of course winter sports. Summer and fall are lovely. Though due to the heat, dryness, and forests, fire danger will keep you on your toes.

See & Do

  • Downtown. Nice downtown area with good restaurants and outdoor shops.
  • The Grove. Cool local neighborhood with a food hall. Like a mini downtown for the locals.
  • Old Mill District. Shopping district.
  • Blockbuster Video. The last one on Earth. Take a trip for some nostalgia, a movie rental, or some swag.
  • High Desert Museum. Very cool indoor and open air museum with artwork, animals, and old homestead. Plan to spend about 2 hours.
  • Deschutes National Forest. Lots of hiking. Mt. Bachelor ski area.
  • Tumalo & Double Falls. Short hike to Tumalo Falls. Keeping going on to Double Falls which is absolutely spectacular.
  • Tumalo Mountain. Great panoramic views. Steep 4-mile round trip hike to the summit, definitely worth it.
  • Todd Lake. Nice chill spot with mountains in the backdrop. Short hike around the lake.
  • Broken Top. Steep off road drive from Todd Lake to the trailhead of this stratovolcano. Requires high clearance AWD vehicle.
  • Cascade Lakes National Scenic Byway. Beautiful drive that takes you past several lakes, including Elk Lake. Several campgrounds along the route.
  • Benham Falls. Nice relaxing hike through the forest along the river to a waterfall. Can park on either side on the east or west side. The biking/walking trail connects the two parking lots.
  • Newberry Volcanic National Monument. Hidden gem. The hike through the lava field to Phil Brogan Viewpoint is awesome and you get great views of the mountains. Late summer, early fall makes for a nice color contrast. You can also drive up to the rim at Lava Butte Lookout. During peak season, you must take a shuttle, but in September you can drive up yourself. Closes around 4 or 5 but you can also walk up if the gate is closed.
  • Smoth Rock State Park. This place is magnificient, must see. Great landscape, cool views, very popular for rock climbing. When I visited, the bridge was out, so I had to (got to?) wade across the river. There was a spot people were crossing that went about mid thigh height at its deepest.

Food & Drink

  • Active Culture. Really great healthy cafe style restaurant. My favorite place to eat in Bend.
  • Wild Rose. Best Thai food in town.
  • Kanona Cafe. Stellar smoothies.
  • Mimi’s Bagel Deli. Food truck with bagels.
  • Market of Choice. Healthy grocery store.
  • Sebastian’s Seafood and Specialty Market. Located at The Grove, awesome seafood selection from fish to frozen eel filet. Also sells all kinds of salts, seasoning, camping food, mostly local, that I’ve not seen elsewhere.
  • The Sparrow. Located at The Grove, nice variety of food. Good for breakfast and lunch. Known for its cinnamon roll.


  • Newberry Volcano. Part of the caldera that’s a bit further out and takes longer to get to is Paulina Peak and Obsidian Flow. Plan to take a couple hours at least. There are campgrounds too.
  • Three Rivers & Sunriver. Two neat little towns just outside of Bend. Cafe Sintra is a good place to eat, named after the town in Portugal.
  • MacKenzie River. Beautiful sapphire blue river.
  • Salt Creek Falls. Short hike to a massive waterfall. Can continue on to Diamond Falls.

3. Oregon Coast

Haystack Rock

Highlights: Beaches, coastal views, waterfalls, forests
Suggest Staying: 1-3 days
Stay Around: Portland or Eugene if day tripping, otherwise pick a coastal town or park
Internet: Weak
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Just about the entire coastline holds treasures and is easily accessible from several major cities. Coastal cliffs make way for ocean views, similar to Big Sur, but is uniquely Oregon. The coast will be cooler than inland if you plan on camping or otherwise staying in any of the coastal cities.

See & Do

  • Cannon Beach & Haystack Rock. Film location for 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 this childhood classic, you will have lit up by now realizing yes this place exists and yes you can visit it!
  • Ecola State Park. Great overlook of the coast and of Cannon Beach.
  • Astoria. In addition to The Goonies, also filiming location for Kindergarten Cop. You can see the Goonies house, which last I heard someone lives in so don’t be obnoxious but do revel, and the jail. Astoria Elementary is just down the street. Don’t expect to be able to go inside, but should be no issue taking a photo. It’s a real, active school last I visited. Just around the corner down by the harbor is a lineup of sea lions, barking and lying on the docks lazily which makes for some fun. Wouldn’t say there’s much else going on in the town itself. While close to Portland, I 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.
  • Tillamook. Situated on the bay, this town is a good place to stop and eat or re-supply. Some nice beaches and state parks to the north and the south.
  • Lincoln City & Road’s End. Recreation area and beach.
  • Yachats. Seafood and coast, what could be better. Two particular coastal spots include Devil’s Churn and Thor’s Well, which if you get close to the specific spot, the water crashing on the rocks does kind of sound like Thor bringing down the heavens. It’s pretty cool. For tiny house enthusiasts, Tiny House Tranquility is a phenominal tiny house and RV park. I hope to see more of these types of communities pop up around the country.
  • Florence. Lovely little town along the coast. Catch some good food at Bridgewater Fish House and Zebra Bar or any of the other nearby restaurants. Definitely a good place to stop and eat. Head over to the coast for more beauitful ocean views. Oregon Dunes National Recreation Area is also nearby.
  • Shore Acres State Park and Cape Arago State Park. Passing through Coos Bay you’ll find more stunning coastal views with some really interesting and unique rock formations as well as a reef that’s home to around a hundred sea lions. Some come closer to the coast and hang out on the beach, others remain on their rock island out in the sea. You can check them out at Simpson Reef Overlook.

4. Crater Lake National Park

Crater Lake

Highlights: Lake
Suggest Staying: 1/2 day
Stay Around: Bend
Internet: Weak
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Absolutely gorgeous. The lake is breathtaking and you can get some great views driving along the rim. You can also hike down to the base and take a boat to the island. It’s a cool hike and you can go swimming down below, or just climb around on the rocks. The hike back up is a bit challenging with all the switchbacks and elevation gain. Bring a jacket depending on the time of year, as it’s quite windy along the rim. You can either make this a quick visit or spend the afternoon.

5. Eugene

Fifth Street Public Market

Highlights: Forests, coast
Suggest Staying: 1-3 days
Stay Around: West or South of Downtown
Internet: Good
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Eugene is a very chill university town with a healthy, hippie vibe. A lot of similarties to Portland and Bend. More of a town to settle or live in versus visit as a tourist, but absolutely worth a stop if you’re passing through. And make no mistake, like other parts of Oregon, there is plenty of nature nearby. One nice thing about Eugene is how centrally located it is for side adventures.

See & Do

  • Skinner Butte Park. City park with views of downtown and the mountains. River access.
  • Delta House. The fraternity house from the classic Animal House. There was actually a fraternity party going on when I stopped by and playing none other than Shout as I drove up. It was kismet. No togas though.
  • Downtown. Cool little downtown area that gives off a college vibe due to the bar scene. There are also restuarants and hippie shops.

Food & Drink

  • Fifth Street Public Market. Area with a bunch of restaurants and shops.
  • Farmer’s Market. Given the number of hippies, it’s no surprise Eugene has an epic farmer’s market on Saturdays.
  • Newman’s Fish Company. Exception fish market with a nice variety of fresh and smoked fish. If you like fish, a must stop!
  • Capella Market . Healthy grocery store.
  • Meraki Coffee Co.. Excellet breakfast and coffee/tea spot. Pretty sure it’s the same as Meraki Cafe in San Diego, but if not, bears a striking resemblance.
  • Jade Dumpling & Noodle House. Dim sum! And other Chinese food.
  • J-Tea. Unfortunately the owners were on vacation when I was there, but looked like a great tea house.


  • Cottage Grove. For you film connoisseurs out there, this is where The General was filmed, starring legendary Buster Keaton. Nice little town if you have some extra time.

Other Considerations

John Day Fossil Beds National Monument

John Day Painted Hills

While there’s not much out in eastern Oregon, this place is a hidden gem. I was on my way out to Idaho in search of hot springs and this was not much of a detour. After seeing some pictures I figured it was at least a good place to break up the drive and stop for lunch. Ended up spending a few hours here exploring the very colorful landscape. I visited two of the three units in this national monument, each of which is about an hour drive apart. The Painted Hills Unit is just what it sounds like. Millions of years of evolution created this incredibly scenic and highly colorful landscape. Be sure to stop at the visitor’s center to read about it. The Painted Hills Overlook is a must see and the Painted Cove Trail was short, pretty, and informative. The Red Hill Trail is short and sweet if you still have some time. Moving on to the Sheep Rock Unit, it’s not quite as colorful, but has some pretty hikes, including the Blue Basin Overlook Trail and Cathedral Rock. This is where the paleontology center is located.

Internet: Weak

General Tips

  • Fires. Prevalent starting as early as July, but ramp up in August and September. Mostly to the east, but the smoke may affect the air quality of places several hours away. Not to mention hiking and other natural areas may be closed off. Plan your trip accordingly, look for fire activity maps/apps (e.g. Google Maps), and definitely be aware of what's happening around you if you plan on camping.

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