Prineville Western Days

Pioneer Park sits in downtown Prineville at Third Street and NE Elm Street, one block east of the Crook County Courthouse. On the weekend of the Crooked River Roundup PRCA Rodeo, its lawn fills with vendor booths, food trucks, and a stage. The festival is Prineville Western Days. It sits at the end of the Roundup parade route, so on Saturday morning the rodeo royalty and Western-themed floats arrive at its edge. Parking is on the residential streets around the park.

The 2026 festival ran Friday, June 26, and Saturday, June 27. One Decision Management, which produces the festival, gave the hours as noon to 6 p.m. Friday and 9 a.m. to 5 p.m. Saturday. The Bulletin of Bend put Friday’s close at 5 p.m. A listing for 2027 gives June 25 at 11 a.m. through June 26 at 5 p.m.

Booths, lemonade, and a stage on the lawn

The producer counts more than 100 vendors. The festival’s Facebook listing says 80 or more and calls it the largest vendor festival in Crook County. The organizer prefers handmade goods, art, and western decor, and the 2026 list ran mostly that way:

• David Edwards sold knives made for sporting, farm and ranch, and kitchen use, with leather sheaths.
• Dave Driftwood Cribbage Boards sold boards cut from driftwood gathered on the Oregon Coast.
• Sunbreak Handmade Goods sewed bags and purses from Pendleton wool and leather.
• Silverwear Jewelry & Etc. made spoon rings from antique silverware, along with horseshoe suncatchers and shell-casing earrings.
• Pencil Prints sold hand-drawn pencil pictures of old homesteads, barns, and churches, described as “true sites of central & eastern Oregon history.”
• Kristi of Diamond S Studio painted the historic western lifestyle in classic realism.
• Ruby Caudell of RC Mae Designs, listed as a 20-year-old artist who has drawn since she was 5, sold prints of her charcoal and pen-and-ink Wild West scenes and wildlife.

Gnomes Needing Homes brought one-of-a-kind gnomes from 4 to 20 inches tall. Willamette Valley Berries brought plant starts, fresh berries, and pies. Last Chance Cafe sold gourmet nuts in more than 15 flavors, among them bacon garlic almonds and chile lime saffron pistachios. Faery Face Art painted faces. Snowshoe Leather Care offered free conditioning for boots, belts, and saddles. That company says it was founded in the Pacific Northwest in 1927, when snowshoes were made of leather and their bindings had to stay soft and waterproof. A home solar installer and a window replacement company also had booths.

Barn Doggies served the lunches: hot dogs, chili dogs, pulled pork sandwiches, pretzels, nachos, and Frito bowls. The snack booths sold Dippin Dots, kettle korn in traditional or caramel, shaved ice from Summit Shaved Ice, and lemonade squeezed in front of the customer at Lemon Squeezie. No alcohol is allowed in the park. Tastee Treat, Cuppa Yo, the Sandwich Factory, and other restaurants are a short walk away.

The 2026 stage schedule booked Frank Carlson on Friday from 1 to 5 p.m. On Saturday, Matt Martin & the 45’s played from 11 a.m. to 2 p.m., and the Just 4 Fun Band followed from 2:30 to 4. The Bulletin noted games for families on the lawn. The event runs rain or shine. When the weather is hot, people sit in the shade behind the stage and under the trees by the old cabin. The organizers ask visitors to leave their dogs at home because the park gets crowded.

Roundup week around the park

The festival is one part of a larger week. In 2026 the Bulletin described Roundup Week this way:

• Thursday through Saturday, June 25 to 27, rodeo performances began each evening at 7 at the Crook County Fairgrounds outdoor arena. Free slack ran in the mornings.
• Thursday was family night, and children 12 and under got in free.
• On Friday and Saturday nights, an afterparty called Linger Longer began at 9:30 with music and dancing by country musician Olivia Harms.
• The Saturday parade stepped off at 10 a.m. The Bulletin gave its route as Northwest Harwood Street to Northeast Fairview Street and called it one of the few parades still to travel Third Street, the town’s main thoroughfare.
• That same Saturday afternoon, the Bowman Museum held “Around the Campfire,” an open mic of Western music and cowboy poetry marking 81 years of the Crooked River Roundup.

Brandi Ebner takes the reins

The festival is older than its current management, but the dossier does not give a founding year. A producer’s page headed “2025 Prineville Western Days” calls it “in it’s 21st year,” and the same page lists the 2026 dates. In April 2017, One Decision Management took the event over. The company is owned by Brandi (Hereford) Ebner, a Prineville resident. She had been executive director of the Crook County Foundation, the Prineville-Crook County Chamber of Commerce, and the Wilsonville Chamber. Her company’s pages credit her with more than 20 years of producing fairs, parades, expos, car shows, and fundraising banquets.

According to the producer, the festival has “grown rapidly” since she took over. Her stated aim is to make it one of the premier community events in the region and to bring new visitors to town on Roundup weekend. Her company also produces a May Market, a Heritage Fest, and a Holiday Market in Prineville.

A boulder and the Wright family’s cabin

The park holds older things than the booths. On NE Elm Street, south of Third, a metal tablet is mounted on a large boulder. The Crook County Pioneer Association dedicated it on August 7, 1938, “in grateful remembrance of the heroic early settlers of the Central Oregon Country.” The tablet records that the Ochoco Valley was first settled in 1867, mostly by people from the Willamette Valley, and that Prineville was first settled in 1871. A contributor to the Historical Marker Database, who photographed the tablet in 2016, described it as weathered and difficult to read.

The old cabin by the shade trees once stood about 22 miles east of town on Upper Ochoco Creek. William Jasper Wright and Annie Laura Howes married on September 25, 1878, and moved to the Upper Ochoco Valley in 1879. Their house was a story and a half, with a three-bedroom loft and two bedrooms below. A kitchen and dining room at the back were built of ordinary lumber and may have been added as the family grew. Four of the Wright children were born there, and the neighbor, Mrs. Ida Blevins, served as midwife.

In 1960 Hudspeth Land and Livestock, which then owned the land, donated the cabin. Workers took it apart, numbered every log and beam, and hauled it into town. They rebuilt it in Pioneer Park as a single story so it would be easier to enter. It opened on July 1, 1960, as Prineville’s first museum, and it served as the county’s main historical collection until the A.R. Bowman Museum opened in 1972. The City of Prineville owns the cabin, and the Historical Society and the Parks and Recreation Department maintain it. It opens from Memorial Day through Labor Day, a season that includes Roundup weekend.