A Summer Weekend in Prineville

Here in the high desert, small-town charm is easy to come by. But what happens when you combine a rich legacy of the old West, affordable vacationing, and a tight-knit community? You get Prineville – a town of just around 10,000 people in Central Oregon. The city’s modern technology mingles with its rodeo heritage and outdoor recreation proximity to create a lively, one-of-a-kind spot that’s full of excitement. Rooted in rural traditions and annual events, this small town is big in spirit and activities.

Nearly every summer weekend you’ll find happenings in Prineville, from concerts in the park and community celebrations to rodeos and races on foot (or yep, you guessed it – bike and horse). Mark your calendars, because Prineville comes alive in the summertime. Whether you’re a Central Oregon native curious to explore more of your backyard, or a visitor looking to get out for a weekend, we’ve got you covered for a two-to-three day adventure in Prineville. Let’s get to it!

Overlook of Prineville.

GRAB A BITE

Prineville may be small but it’s mighty, and the food scene is no exception. With Facebook and Apple in town, new cart pods, breweries, and restaurants continue to open up. Read on to discover all the insider tips on local fare for your long weekend stay.

Food at a Bar.

Traveling with the family? Check out The Waterhole and their homemade sourdough, Creekside Food Court for food trucks and a beer garden, and Sandwich Factory across from the historical courthouse. Don’t skip on local, old-school favorite Tastee Treat for its hand-cut fries and great burgers, ice cream, and more yummy fare (you can’t miss the iconic neon ice cream sign).  

For a Central Oregon vibe: Wild Ride Brewing, which began in Redmond, is opening up another location in Prineville (May 2022) as a lively spot for great beer and various food trucks. In addition, Crooked River Brewing downtown is a fantastic option, and Dillon’s Grill has games on-screen and classic burgers and beer. 

On a town stroll: Every Saturday from June to September, follow the sweet scent of fresh produce. Crop Farmer’s Market is held downtown at Stryker Park from 10am-2pm, and with its proximity to local farms, the pickings are top-notch. Stop by on your way into town for Central Oregon veggies, locally-raised meats, live music, and artisan goodies before your activities.  

21+ nightlife and breakfast: The Horseshoe Tavern is not only Prineville’s oldest bar, but its open mic nights, pool table, live music, and weekly food specials make it a hot spot. Their breakfast is drool-worthy, too (don’t sleep on the chicken fried steak and bloody mary’s. You heard it here first!)

For date night eats: Stop by Barney Prine’s Steakhouse and Saloon or Club Pioneer for those times you want to spice up the routine and grab a prime rib.

STAY OVERNIGHT

Whether you want to spend a night out in the woods, wake up by a gently flowing river, or slumber in town, Prineville is an experience all its own. The town is bound to get crowded during summer, and you’re guaranteed to run out of daylight quickly. So – let’s get your lodging squared away for a weekend to remember.

Feeling fancy? Hang that cowboy hat you just bought in town at Prineville’s Men’s Wear for a night or three just out of town at Brasada Ranch

In-town ease: Peek at the cozy array of Airbnbs’s, or seek out the major hotels. 

Stargaze & pitch a tent: Sleep under the stars or park your RV at Prineville Reservoir State Park. If rustic is more your style, see what the Ochocos has to offer, or check out the Wildcat Campground (located just 30 minutes out of town!)

Campground at Prineville.

TAKE A DOWNTOWN CRUISE

Get a feel for a downtown that has all the vibes of the old mixed with the new. Before you stroll, check out the Ochoco State Scenic Viewpoint on the way into town, which affords a memorable view of the entire city.

Downtown Prineville shop.

THE BOWMAN MUSEUM
Up for a meander-and-learn museum moment? Located in the historic Crook County Bank building, the Bowman Museum is free to the public, with new exhibits each year, artifacts, pioneer furniture, and all kinds of Central Oregon history. Stop by anytime Tuesday through Friday 10am-5pm, or Saturday from 11am-4pm. If you’re a fan of souvenirs, pick up a book or gift for the history buff in your life.

THE PRINEVILLE CHARM TRAIL
Iconic charm is a thing here. Why not wear it? Embark on a treasure hunt without having to leave town by following the Prineville Charm Trail. Stop in at the Chamber of Commerce and Visitor Center to get a map and bracelet. Each time you venture to one of the 29 different locations in town, you’ll add a charm to your bracelet. Get your shopping on, see the town, and have something to show for it. It’s a win-win.

THE OUTDOOR DAY TRIP

Feeling adventurous? Luckily, Prineville has some of the best outdoor recreation in Oregon. Summer is the perfect time to head out on a day trip during your long weekend stay. Read on for the top excursions Prineville is known for.

GET YOUR SWING ON
Central Oregon loves its golf, and Prineville’s own Meadow Lakes Golf Course is one of the best bargains out there. With summer rates as low as $20 per nine holes or $37 for 18 holes during the week, it’s a total steal.

Fun fact: did you know that the golf season lasts longer in Prineville than in most of Central Oregon, due to the lower elevation and milder climate? Be sure to hit up the in-town course and take advantage of affordable deals and scenic views.

PADDLE, FLOAT, FISH
Want a break from the often-busy Deschutes River? Take your paddleboard or tube on a warm-day cruise along the Crooked River instead. Get ready for a 2-3 hour adventure if you decide to float, and try to go when the water is the deepest in May or June. Or, pack your fly-fishing gear and throw a line in. Fellow anglers are few and far between here, so try your luck at fresh rainbow trout and whitefish.

TAKE A HIKE
Feeling like fresh air? Just outside Prineville and beyond, hit the trail for a day trip or half-day excursion.

Half-day at Barnes Butte or Stein’s Pillar
Located just 1.5 miles from the city center on the east side of town, Barnes Butte Trail is a shorter favorite with a pretty summit. Dogs are allowed on leash, but you’ll have to leave your bike at home. If for nothing else, go for the views: on a clear day, there are 360’ of the Rimrock, the Ochocos, and the Cascades.

For when you want to leave the city, but not go too far, head out to Steins Pillar Trail. A quieter version of Smith Rock, the mostly uphill and curvy trails clock in at a total of just under four miles round-trip. It’s a bucket-list beauty – depending on the time of year, you may even see wildflowers!

Prineville Reservoir.

Full-day at Painted Hills
Brace yourself for otherworldly colors. Visit the Painted Hills and the John Day Fossil Beds National Monument just over an hour east of Prineville. The Painted Hills are one of three units comprising the John Day Fossil Beds National Monument, with mounds and rolling hillsides covered in red, yellow, and other vibrancy. Take the short winding trails to big views (and don’t forget your camera!)

On your way back, cool off in Powder House Cove at Prineville Reservoir.

BIKE IT OUT
The Crooked River Canyon Scenic Bikeway is a classic 5-star road bike route and a total gem. In addition, the 66 Trails are a compact but fun trail system within Prineville city limits, with a couple of loops and short technical sections. The location and terrain provide you with an unforgettable view of the city of Prineville. In 2014, Good Bike Co. opened in town offering bike sales, repair, and rentals. Be sure to stop in and speak to James or Amy for all the best tips on bikepacking, mountain rides, and all the single track you could ever want.

THE MAJOR SUMMER EVENTS

Did someone say rodeo? Prineville is known for its downtown park concert series, county fair, a bustling 4th of July celebration, and the signature Crooked River Roundup. You’ll want to pencil in these Central Oregon signature events.

The Prineville Fairgrounds.

Rodeo & rally: From June 23rd to 25th, the town rodeo draws some of the top talents in the world. Drop by Pioneer Park for western-themed floats, hundreds of spectators, kids activities, music, and more. 

Have plans for the 4th? Celebrate Independence Day in Prineville. Expect a parade, early-morning pancake breakfast, and the Splash-n-Dash event that includes a pool swim, bike, and float down the Crooked River. Pop by the beer garden and day-long events at Ochoco Creek Park, and end the epic day with fireworks at the lookout. 

Feeling lucky? Block out July 13th-16th in your calendar for the Crooked River horse races at the county fairgrounds. Place some bets and feel that small-town energy with thousands of Central Oregon natives (and beyond). 

The free August fair: Experience the epitome of Central Oregon summer at the county fair in August. It’s a staple summer event in Prineville, so bring the whole family. Wander the fairgrounds for amazing food, livestock, 4-H exhibits, and more. 

With endless options and places to see, Prineville is a must for a two-to-three day summer trip. If you’re looking for small-town charm, local attractions, outdoor adventures, or some unwinding by the river, you’ll find it all here – and then some.

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