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Digital Nomading Chapter 3: Portland and Bend, Oregon

11–16 minutes

In August 2025, I started on a six-month digital nomad trip around the U.S. My plan is to live in different cities for a few weeks to a month, to explore each location more deeply than a normal vacation would allow, and figure out where I want to live long-term.

Portland and Bend in Oregon were the third stop on my trip, a brief chapter after a month each in Seattle and Denver and a week in California to hike Mount Whitney. I’d visited Oregon in the past, but only spent time in the southern part of the state to see Crater Lake and the southern coast.

I spent four days each in Portland and Bend, which gave me the chance to explore some neighborhoods, food, and nearby nature. I’d love to come back in the future to explore in more depth. Here are my takeaways and reflections from visiting Portland and Bend for a week.

Portland

What I liked about Portland

  • Fantastic food scene. Portland punches above its weight food-wise, among the top U.S. cities for food in my book. Not too expensive, good portions, overwhelmingly incredible dishes.
  • Great coffee culture. Lots of coffee shops open late, high quality coffee, cute outdoor spaces, etc.
  • Quirky, artsy, and interesting neighborhoods. Alberta Arts District (where I stayed) is an awesome place to spend some time and explore – Great shops, food, etc. I expected Portland to be similar to Seattle, but I thought Portland’s neighborhoods had a lot more character than Seattle’s.
  • Lots of green spaces.
  • Great and diverse nature nearby. Oregon Coast within an hour and a half, an old volcano and plenty of hiking trails right in town, waterfall hikes within an hour, mountains (Mount Hood, Three Sisters, Mount Rainier, etc.) within an hour and a half to three hours.
  • No sales tax!

What I didn’t like about Portland

  • Relatively poorly connected airport. Expensive to fly in and out of PDX. Connections to other airports are often required, even to fly domestically.
  • Rainy. We had good luck (sun) for a couple days and the weather was perfect, but it was raining 70% of the days we were in Oregon.
  • Lots of traffic, somewhat confusing roads. I say this about every city I visit
  • Questionable safety in certain areas. The downtown donut shop had their own private security guard and certain areas felt a little unsafe.
  • Mountains aren’t super close by. I’m comparing this to Denver (a high bar), but it seems more difficult to go for an after-work hike in the mountains in Portland than in Denver or SLC. There are city hikes and waterfall hikes close by, but hikes in the mountains (especially hikes at elevation) are a bit harder to reach.

Best things I did in Portland as a digital nomad

Hiking and nature

  • Cannon Beach: Iconic beach on the Oregon Coast, known for its rock formations (Haystack Rock is really cool). We tried to come for sunset and it was cloudy, so we didn’t get much, but I still really loved it. Saw lots of starfish!
  • Columbia River Gorge: To be honest, I wasn’t crazy impressed by the nature at Columbia River Gorge, but the waterfalls were still nice to visit, and it was great to have hiking trails so close to Portland.
    • Multnomah Falls: Tallest waterfall in Oregon, the view with the bridge in front is very pretty. I made the mistake of hiking the entire loop, when the best view of the waterfall is right next to the parking lot. The trail to the top of the falls was short but steep, and it yielded a very disappointing view.
    • Wahkeena Falls to Fairy Falls: Wahkeena Falls is pretty much right off the parking lot, nice waterfall but nothing crazy. Fairy Falls is a short but steep hike away, the trail is very empty. Fairy Falls is pretty small and also not super impressive, but quite pretty. Wouldn’t go out of my way for either, but the hike was enjoyable enough.
    • Latourell Falls, Bridal Veil Falls, Shepperd’s Dell Falls: All within less than half a mile from their respective parking areas, not very impressive.
  • Silver Falls State Park: Known for the Trail of Ten Falls, where a relatively short loop passes by ten waterfalls, many of which you can walk behind during the hike. Trail was a bit muddy, not slippery, and well-maintained. The waterfalls were nice, and there were beautiful rainforest views along the hike.

Exploring the city

  • Alberta Arts District: Street full of really good food, galleries, quirky boutiques. Very safe and walkable.
  • Downtown Portland: A bit rough around the edges, but has some great spots.
    • Portland Visitor Center: The people who work here are really nice and happy to answer any questions about Portland. Some great maps / information here as well, along with free Portland stickers and a buy-one-get-one coupon for Salt & Straw!
    • Powell’s: Massive bookstore with four floors and themed rooms named after colors. The size of the bookstore is absolutely insane and there are hundreds of books on every topic.
    • Portland Gear: Cool store with a selection of Portland-themed clothing. I really liked their designs, even if the fit wasn’t right for me.
    • Tender Loving Empire: Portland and Oregon-themed souvenir store.
    • Kiriko Made: Japanese design store, some cool furniture, decor, and clothing.
  • Tillamook Creamery: The factory where Tillamook produces its dairy products. This was surprisingly one of my favorite experiences – Free cheese and ice cream samples, a self-guided tour of the factory, a huge gift shop with a lot of cool things, and great food and ice cream to order!
  • Mount Tabor: A dormant volcano at the heart of Portland, with views of Mount Hood on one side and views of downtown Portland on the other, lots of trees at the top. One of my favorite city parks of all time. Great spot to watch the sunset.

The best food I ate in Portland

  • Memoire Ca Phe (Alberta Arts District): My personal favorite place that I ate Portland, I went four times during my four days in the city. Their protein bowl (pork sausage, fish sauce bacon) is basically perfect (great flavor, crunch, unique, big portion). The black sesame waffle is also fantastic and tastes just like butter mochi. I would skip the egg coffee though, it was about 400% too sweet.
  • Sanae Thai (Alberta Arts District): Large portions, reasonable prices, great food. Pad thai with chicken was not too sweet (great balance) and roti with thai tea “jam” was a great dessert, loved that the thai tea flavor came through very clearly.
  • Gumba (Alberta Arts District): Casual Italian spot, the food was pretty expensive, came out fast and was very good. Had the vodka sauce gnocchi with mushrooms, no complaints, great dish, although it was supposed to be spicy and it definitely wasn’t.
  • Tillamook Creamery (Tillamook, OR): The smoky sausage mac and cheese was probably the best mac and cheese I’ve ever had, great flavor, very generous with the sausage (I do wish there was more pasta and that they gave a bigger portion for $17). Their espresso chip ice cream (seasonal flavor) was also phenomenal. The butter pecan ice cream left a lot to be desired though – didn’t have much butter flavor (tasted like sweet cream).
  • Yaowarat (Montavilla): Chinese-Thai fusion spot, moderately expensive with medium portions. Their kway teow is fantastic, great crunch on the noodles, not too salty which is tough to do. The toasted buns with pandan custard were the star of the show, perfectly toasted bread and the custard was delicious – the best dessert I’ve had in a while.
  • Roseline Coffee (Multiple locations): Great place to get some work done (although the wifi didn’t work for me), the people who work here are really nice, and they don’t mind people sticking around for a few hours. It also had one of the best chocolate almond croissants I’ve had at a coffee shop. Great iced coffee with free(!) oat milk.
  • Bollywood Theater (Alberta Arts District): Restaurant / bar, quite pretty. Chicken tikka bowl tastes great, not a traditional tikka masala (included chickpeas, which was delicious). Wish there was more chicken (dish only included two small skewers).
  • Fifty Licks (SE Division): Ice cream shop with Asian-inspired flavors. I really loved the black sesame and mango sticky rice flavors. Everything I sampled tasted just like the flavor it was supposed to be.

Bend

What I liked about Bend

  • Nature. The nature access in Bend is ridiculous. Trails along the Deschutes River right in town, mountain trails across the Three Sisters Wilderness within 40 minutes to an hour, Smith Rock within 40 minutes, Lava Butte, etc. Bend itself is also beautiful, especially as the leaves are turning.
  • Nice people. People generally seemed to be very happy, and they were very friendly!
  • Good food for a city of its size. Food in Bend and the nearby town of Sisters wasn’t the most amazing food I’ve ever had, and some places were a miss, but for their size and population, I was really impressed by several of the places I ate.

What I didn’t like about Bend

  • Congested. There was a surprising amount of traffic for a small city.
  • Expensive. In my experience, Bend was far more expensive than Portland, and it felt more difficult to find a sizable dinner for less than $20, which was absolutely no problem in Portland. There were lots of restaurants where prices were shockingly high (e.g. garlic naan for $7, pad thai for $25, seven momos for $25) compared to prices even in cities known for a high cost of living.
  • Diversity. I think I saw maybe a total of ten people of color while in Bend.

Best things I did in Bend as a digital nomad

Hiking and nature

  • Smith Rock State Park: As someone who primarily loves alpine lakes and mountains, I was surprised by how much I enjoyed Smith Rock State Park, which is a high desert canyon known as a rock climber’s paradise. We did the Misery Ridge – Summit Trail Loop, which starts very steep up and down with amazing views of the canyon and river, winds around to some pretty boring views but nice gradual incline, and ends with a walk along the river.
  • Three Sisters Wilderness: Hiking trails around the Three Sisters, a group of volcanoes. It was very snowy and the weather was bad when I visited, so I only got to hike part of the Tam McArthur Rim Trail. I still really enjoyed it and want to come back to hike the South Sister and some other trails in the area. Permits are required for each trailhead from June 15-October 15.
  • Lava Butte: Lava Butte was a victim of the government shutdown, where the road leading to the top was closed (with no warning). We could still walk to the top but opted not to, since it was raining that day. The volcanic rock and the butte are still cool to stop by and see.
  • Deschutes River Trail: This trail has several smaller sections all around Bend. I walked the section to Benham Falls. It was very flat, short, and enjoyable, with nice views of the fall foliage and the river.
  • Sahalie & Koosah Falls: Sahalie and Koosah were the most impressive waterfalls of the trip for me. They’re also both a couple hundred feet from the parking lot, so very easy to stop by and see (no need to walk the connecting trail between the two).
  • Clear Lake: I liked Clear Lake more than I thought I would. The water is so blue and very clear (as the name suggests) and the surrounding lodge feels very rustic. Really nice place to stop by on a sunny day.

Exploring the city

  • Downtown Bend: Downtown Bend has a lot of great shopping and food.
  • Downtown Sisters and Harvest Faire
    • I was lucky enough to be in Sisters during the Harvest Faire, held the second weekend of October, when hundreds of local vendors sell food and crafts in an outdoor market. Some of my favorite stalls were Jacobsen Salt, Dave Fox Studios, Charlotte Wallace Art, and Michelle Michael Studio. There was also a live band (I didn’t catch their name) that was fantastic.
    • Beyond the Faire, I enjoyed walking around Sisters and stopping into a few shops. There are several stores peddling outdoor gear and Oregon souvenirs that are worth a visit.

The best food I ate in Bend

  • Lone Pine Coffee Roasters (Downtown Bend): Very busy, relatively expensive, good coffee, fantastic quiche, pretty good pastries. Beautiful space, good spot to get some work done.
  • Wild Rose Northern Thai (Downtown Bend): I don’t see many Northern Thai restaurants in the U.S., especially restaurants that only do Northern Thai instead of the more popular dishes. We went here three times during our four days in Bend. Highly recommend the khao soi (delicious although the portion is kind of small), curry basil noodles and street noodles (big portions), and sweet sausage fried rice (could’ve used a bit more sausage).
  • Sisters Bakery (Downtown Sisters): Sisters Bakery was shockingly good. We tried ten items here and pretty much every single one hit. My favorites were the chorizo chimichurri scone, chocolate croissant, pumpkin scone, ham & cheese croissant, and cinnamon roll.
  • Bonta Gelato (Downtown Bend): I will be raving about Bonta Gelato for a long time as the only ice cream place I’ve ever been that’s really mastered the chocolate flavor. Their salted chocolate flavor is pretty much perfect – It tastes exactly like a brownie and is not too sweet or overwhelming. Their other flavors (peanut butter, coffee chip) also did a great job representing the flavor without being overpowering and too sweet.

Conclusion

Based only on my very short stint here, I don’t think Oregon is my personal frontrunner in terms of a place to live – I want a place with both a more well-connected airport and slightly better access to mountains and alpine lakes.

Overall, my week in Oregon was absolutely awesome, and I can’t wait to return to explore more of Portland’s neighborhoods, drive more of the coast, and visit Bend in the summer, when the weather is better for hiking. I’ll also be dreaming about the incredible food in Oregon for the foreseeable future.

What’s next?

I’ll be taking a short hiatus from my digital nomad trips to spend a couple weeks in Charlottesville, VA. After that, it’s off to Moab, Utah for a few weeks before taking a vacation to Guatemala and El Salvador.

Read about my experiences digital nomading in other cities here:

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