Must See Things to Do in Prineville, Oregon

Our travel therapy adventures led to us spending 3 months in Prineville, Oregon.

Prineville is a small town outside of Bend. You’ve probably heard of Bend. Prineville is a 40 minute drive away.

Bend is a hippy town. Prineville is not. Prineville is Bend’s conservative uncle. While Bend has exploded with growth and change, Prineville seems like it hasn’t changed much in the last 50 years – and the locals like it that way. Fair enough.

Yes, Prineville can be rough around the edges. But we still had a great time exploring Prineville and everything it had to offer.

Here are the top must see sights, experiences, and things to do in and around Prineville, Oregon.

1) Drive to the Painted Hills

Many people stop in Prineville on their way to the Painted Hills. We visited the Painted Hills while living in Prineville, and they’re absolutely worth a visit if you’re in the area. The Painted Hills are one of the seven wonders of Oregon (yes, that’s a thing).

2) Drink

For a town with fewer than 10,000 people, Prineville has a surprising number of great places to grab a drink.

I’ve been to other small towns in America – like Edenton, North Carolina – where it was tough to find a good bar. There were 10 churches and like 2 bars.

Fortunately, Prineville is a fantastic place to grab a drink. Some of my recommended places around town include:

The Horseshoe Tavern: You’re guaranteed to meet some characters. It’s everything a country bar should be. People were always friendly to us. The fries were great. Drinks are strong and cheap. Great live music on an outdoor patio. After living close to The Horseshoe Tavern for all 3 months we lived in Prineville, we became very familiar with it.

Sons of Beer: Owned by the same people as The Horseshoe Tavern, Sons of Beer has plenty of fantastic craft beer on tap along with decent pub food. Don’t miss their Wednesday deal. You get pints of amazing craft beer for $3.75 and a burger basket with fries for $6. You won’t find a better deal in town.

Club Pioneer: Club Pioneer is a restaurant established all the way back in 1942. It’s a genuine Prineville tradition. We always had good meals at Club Pioneer, and it’s probably the fanciest restaurant in town for a date. If you want a nice cocktail in Prineville, Club Pioneer is a great option. There’s also a separate bar area if you want more of a saloon experience (enter through the left door instead of the right).

Dillon’s Grill: Owned by the same people as Club Pioneer (are you sensing a pattern with Prineville?), Dillon’s Grill is tucked away down a weird street but offers great food and drinks, including a full bar and a lineup of craft beer. Like Club Pioneer, there are separate sections for the bar and the family restaurant.

Barney Prine’s Steakhouse & Saloon: Located just off Prineville’s main road, Barney Prine’s is an okay steakhouse and bar with one of the nicer patios in Prineville. If you want happy hour drinks with steakhouse-style appetizers, then Barney Prine’s is a good option.

3) Drive Through the Ochoco Reservoir

If you drive south of Prineville for around 10 minutes, you’ll reach the Ochoco Reservoir. The winding road takes you past hydroelectric dams, impressive cliffs, and other picturesque sights. It’s a great Sunday drive.

4) Visit Smith Rock State Park

Smith Rock State Park is probably the most popular outdoor area in the Prineville/Redmond area. Fortunately, it lives up to that reputation. Yes, the parking lots get crowded on weekends, but Smith Rock State Park is a spectacular place to walk around.

5) Visit a Brewery

Prineville has two breweries, both of which serve surprisingly good beer and food. I would recommend the food and beer at both of Prineville’s breweries:

  • Ochoco Brewing Company
  • Crooked River Brewing

Both are proper brewpubs, although they work in slightly different ways.

Ochoco Brewing Company has a full lineup of its own beers. Founded in 2009 by a local couple, Ochoco Brewing Company makes fantastic beers, and they sell growlers for just $9 to $13. I lived above this brewery (literally) for 3 months – and it was dangerous being that close to affordable craft beer. Their Taco Tuesday is also surprisingly tasty, with cod, steak, and fish tacos available for $2 apiece.

Crooked River Brewing Company also has a full-service restaurant on site, although they work slightly differently than Ochoco. Crooked River Brewing has a few of its own taps on the menu, although most beers are from other Oregon breweries. They make fantastic pizza, and I love the burger food truck outside.

Honestly, if you’re spending an hour in Prineville driving through, go to Ochoco Brewing Company or Crooked River Brewing. Both are fantastic breweries with great food – I would even call them two of the  best restaurants in town.

UPDATE: Ochoco Brewing decided to close its doors in 2020. Unfortunately Prineville is doing to having just one brewery.

6) Hike Brown Butte to the Cross

You can do more in Prineville than drink. If you look at Prineville on a map, you might assume the entire town is flat. However, Prineville has more hills than most people realize, and those hills have hiking trails, mountain walks, and viewpoints.

Brown Butte is one such trail. Located above town, Brown Butte is an easy 2-mile hike suitable for all ages. You get a great viewpoint above town. Walk to the cross for one of the best views in Prineville.

7) Visit Tastee Treet

Another Prineville tradition, locals really seemed to love Tastee Treet. It has a drive through.

8) Drive to Ochoco State Park for a View Above Town

Prineville is in a valley surrounded by cliffs. You can drive up to the top of one of those cliffs to get a great view above town.

Grab a bottle of wine and some cheese and crackers, then come up here for sunset. Prineville isn’t the prettiest place in the United States, but it looks really good from up here as the sun sinks below the horizon and the lights come on below you.

9) Visit the History Museum

Prineville has a good history museum in the heart of downtown. Prineville was destined to be a big city like Bend, but the railroad passed it by. The locals fought back by building their own crowdfunded railway, allowing the town to remain a logging center for decades.

Les Schwab (yes, the tire guy) also played a big role in Prineville history. He launched Les Schwab from Prineville, and it grew to become one of the largest tire companies in the western United States.

The history museum dives more into all of this history and much more. We spent about an hour there.

10) Close Down the Horseshoe Tavern

I’m from a small town, and the Horseshoe Tavern is everything a small town bar should be.

Like Prineville, the Horseshoe Tavern is a little rough around the edges – but it’s something you should experience to get a good feel for the locals. As a random dipshit Canadian, I had a great time every night we spent at the Horseshoe Tavern.

Tip: Stick to mixed drinks and beer. My partner made the mistake of trying to order white wine. It was…not good. Or white.

Where to Stay in Prineville

Prineville has like 6 hotels, but only 3 of them are on the usual hotel websites. We stayed in Prineville’s Country Inn & ­Suites  before finding a place to rent, which is technically the best hotel in town (not a big deal).

Hotel options in Prineville include:

Country Inn & Suites: Probably the nicest hotel in town.

Best Western Prineville Inn: Probably the second nicest hotel in Prineville.

Econo Lodge: Very affordable and very basic in the heart of downtown Prineville.

You might be shocked at hotel prices in Prineville. For a random, small town in the middle of nowhere, Prineville hotels are surprisingly expensive. From May to October, expect to pay $110 to $150 for a decent hotel in Prineville.

Final Word: Prineville is Worth Visiting

Prineville, Oregon exceeded my expectations.

The town has nice parks and walking trails. People are friendly. There are enough restaurants, breweries, and pubs in town to keep you entertained.

I wouldn’t go out of my way to visit Prineville. But if you want a slice of small town, rural, conservative American life, then Prineville is 25 minutes off the highway from Bend and Redmond.  

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