Bend/Sisters, OR

Bend and Sisters were two distinct options in the original 43, but they are only 30 minutes away from one another and we spent our five days in the area jumping back and forth between them. Bend is the big city in the area, with a population around 100,000, yet the airport is in Redmond (a town about 1/3 the size of Bend, and which creates a nice triangle with Brnd and Sisters. We didn’t spend any time there, which is why it’s not included in this assessment.) Sisters, named after the Three Sisters Mountains, is relatively tiny – only 3,000 people – yet it is a popular vacation destination. Both spots are popular for outdoor enthusiasts, and more recently, remote workers like us.

The region is covered in sparse ponderosa pine forests, and a big portion of the surround lands are designated BLM and national forest. There are lots of creeks that ultimately feed into the Deschutes River, which flows through Bend. Mount Bachelor is a prominent stand-alone volcano which offers 360° skiing.

Bend: My first impressions were negative – it feels like a city that has a lot of wealth and not much unique character. However, after a few days we eased into it and found some spots that felt more local. We especially like eating Northern Thai food at Wild Rose and walking alongside the Deschutes River whitewater park. Plus, rich-people towns have nice things: plenty of parks, a free showing of Shrek at the Tower Theater, free life vests and helmets available at common River put-ins, nice walking trails…you get the idea.

Sisters: I kept needing to remind myself that I was in Oregon, not Wyoming or Montana, because Downtown had a strong western theme. Despite its small population, there was a lot of offer, including two bakeries, cheap public showers, and miles of trails walking distance from downtown. Everyone we talked to was enthusiastic about potentially welcoming two new remote workers, and the town seems to pride itself on being adaptable.

The Good

• Tons of outdoor access without having to sacrifice city amenities.
• East of the Cascades and far enough south that dreary darkness is not a concern. Yet, close enough to the Cascades that you can go out for a mossy fern-filled day hike. 
• Open to remote workers. By some measures Bend has the highest percentage of remote workers in America. We would have a built in community.
• Trails galore, and would be great for Cameron’s running goals. 
• In summary, we are the exact demographic that area caters to: van-owning digital nomads who are looking to settle down in a well-balanced community. 

The Bad

• Too expensive and too many rich people.
• It’s already discovered. In my fantasy, we’re the first of our kind to happen upon an undiscovered gem. 
• Seasonal influxes could probably be annoying.

The Verdict

Yes. There is a lot here that is our wish list, but the big hesitation is that this area has already been discovered. Do I really want to jump on the bandwagon?

Biking, both road and mountain biking, is a big deal in this region. There are tons of cycling shops and I saw this Oregon bike in both towns (this one was in Sisters).

Picture-wise, let’s start with Sisters.

Despite its size, there seemed to be some in-town entertainment.

We spent a lot of time working here. The Village Green is a little park a few blocks from downtown and less than a half mile from the Deschutes National Forest. Plus, we were able to shower for $0.25/minute. 

We parked in the forest overnight, and ran/hiked along the trails during the day. The Sisters Trail Alliance is actively working on new trails.

Like all of the areas that appeal to us, Sisters has an expansive trails system.

We only tried one of the two bakeries, Sisters Bakery, but I throughly enjoyed everything we got there. 

We also checked out Sisters Coffee Co. The inside was a good representation of Sisters: artsy/country/homey.

Food-wise, we also did an impulse stop at this food truck court. We went with the tacos. 

Architecturally, it seemed like you could plop this town into a more western cowboy state. 

Sisters isn’t big, but it had a community feel. This center plaza is where events, like the seasonal farmers market, take place. 

The Three Sisters, as seen from Sisters.

And with that, we’ll transition out of Sisters and head over to…

…Bend. There was a pair artists who created a series of “welcome to” murals across Cental Oregon. 

Some highlights in Bend included the whitewater park (there were a few kayakers practicing their surf),…

…the walking trails,…

…the variety of food options (this was Wild Rose),…

…and the seemingly abundant entertainment options. As mentioned, there was a free showing of Shrek one of the nights we were in town. 

For whatever reason, downtown felt a little soulless to me. It was large, but everything felt new, trendy, and transitory. I wouldn’t be surprised if over half of the businesses get replaced within five years for whatever the new trendy vibe is. 

That said, I would love to eat at the Jackalope Grill if it’s still around the next time we’re in bend. Of course I love the name, but the menu sounded good, too.

The part of the Deschutes River that runs through town is gorgeous. 

I don’t know why, but this outdoor theater and the background smokestacks seemed to be iconic locally. 

We ended our time in the area skiing at Mount Bachelor. Unfortunately it got cold and windy, and the two lifts that service double diamonds were out of commission, so we didn’t have a great time.

We’ll finish it up with our view of the Sisters from Mount Bachelor before the clouds came in.