The cattle drive provides visitors a unique Western treat during Crooked River Roundup Week. (Central Oregonian)

Prineville will soon transform into cowboy town thanks to the launch of Crooked River Roundup Week, loaded with events to commemorate the iconic local rodeo.

The weeklong list of festivities starts Tuesday evening, June 24, with the Crooked River Roundup Foundation’s banquet fundraiser and continues through Saturday night when rodeo action concludes.

The Foundation’s banquet will take place under the tent at the Crook County Fairgrounds. Scheduled from 5-10 p.m., it will feature a tri-tip dinner and silent and live auctions. Miss Rodeo Oregon Mary Olney will be the guest speaker and young rodeo athletes will be giving roping demonstrations at the event.

“Our mission is preserving the Western way of life,” explained Foundation Development Director Michele O’Hara. “We bring in people from all walks of life who share a passion for farming, ranching, rodeo and animal health and wellness.”

The funds raised at the banquet and other funds support youth scholarships and pay expenses for local kids involved in such organizations as 4-H and FFA.

“People can go to our website and purchase tickets,” O’Hara said. “It’s really a great opportunity to see the work of a lot of the organizations that are in farming, ranching and rodeo.”

Roundup Week picks up a lot of steam on Wednesday, June 25 with the Stampede Street Party and the annual cattle drive. The street party, hosted by Prineville-Crook County Chamber of Commerce, will take place on a four-block radius on North Main Street from 5-9 p.m. The event will feature live music by Countryfied, food vendors, kids games and more. A chili cookoff, where the Prineville Police Department, Crook County Sheriff’s Office and Crook County Fire and Rescue compete for culinary bragging rights, begins at 5 p.m.

The party will pause for the cattle drive. At 5:30, the cattle will depart a few blocks north of the party scene and travel south down Main Street toward the fairgrounds.

“We will have a Western shootout happening after the cattle gets through,” said Chamber Tourism Director Kim Molnar. “It is a re-enactment and will be pretty exciting.”

Thursday, June 26 the Crooked River Roundup Rodeo kicks off with gates opening at the Crook County Fairgrounds Outdoor Arena at 5:30 p.m. and rodeo action starts at 7 p.m. Rodeo action will continue at the same time on Friday and Saturday evening, June 27 and 28.

Also scheduled for Friday and Saturday is Western Days, a family friendly attraction at Pioneer Park that features many food and craft vendors as well as games and music. The event will take place from 12-6 p.m. Friday and 9 a.m. to 5 p.m. on Saturday.

Saturday will also feature a variety of events throughout the community. The Crooked River Roundup Parade will start at 10 a.m. Traveling down Third Street from Harwood Street to Fairview Street, the parade will feature numerous Roundup boards and rodeo royalty as well as a host of floats and other attractions.

Then, on Saturday afternoon, people can visit Around the Campfire, a Western music and cowboy poetry event. Taking place from 1-3 p.m., the Associate Membership Group of the Crooked River Roundup presents an open mic event for amateur poets and singers to read their poems or sing their songs. This is a sanctioned event of the International Western Music Association – Columbia Chapter.

Tom Swearingen is the master of ceremonies again this year. His awards include 2019 and 2022 International Western Music Association Male Poet of the Year.

Oregon’s 2025-2026 Poet Laureate, Ellen Waterston will also be participating. She lives in Bend and is the first Oregon Poet Laureate from east of the Cascades. She will read and help with the judging of this family friendly event.

“We appreciate Ellen spending time with us in Prineville,” said Phil Burgess of the Crook County Historical Society. “Prineville is the self-proclaimed ‘Cowboy Capital of Oregon’ and we believe this event fits perfectly with the emphasis of preserving the western way of life and cowboy traditions. In essence, Prineville’s long-standing connection to ranching, its large-scale annual rodeo and horse racing events and the strong community commitment to preserving Western traditions contribute to its ‘Cowboy Capital’ identity.”

Rick Steber, Prineville author of more than 50 books, will also be reading.

Organizers are encouraging all age groups to participate in reading or singing.

“We are looking forward to a large crowd as spectators at the Bowman Museum Community Room,” Burgess said. “It’s been said by some that cowboy poetry is ‘poetry with dust on its boots.’ Come see for yourself. We know you’ll enjoy being ‘Around the Campfire.’”