Long before the cowboys ride horses, rope calves and wrestle steer, one of Judy Holliday’s favorite parts of Prineville’s Crooked River Roundup takes place. “When you see everyone coming in through the gates, smiling and having a good time — that’s it right there,” she says. ”All the work, the sweat and the hours to make this happen, it’s all worth it.”
Judy and her husband, Chuck Holliday, were raised in Prineville — about a 45-minute drive northeast of Bend. They have fond memories of attending the rodeo as kids and have been involved in putting on the event in various capacities over the past 25 years. They’ve passed their love down through the generations.
In 2025 Judy and Chuck were the roundup’s grand marshals, their son Steve was the president of the all-volunteer Crooked River Roundup Association, and Steve’s daughter Corley was the Crooked River Roundup Rodeo Queen. The generations of involvement, the family says, stem from a deep pride in where they’re from.
“Prineville is the kind of community where, when the football team goes to state […] people come out to line the streets and cheer,” Judy says. “It’s that small town where everybody’s friendly. We want everyone coming into town to feel that, to feel that they are welcome.” Here’s how three generations of the Holliday family enjoy the annual rodeo, and how you can experience it as well.
Experience a Rodeo in Oregon’s Cowboy Capital
Every summer an excitement falls over Prineville as residents get ready for the roundup. It’s a weeklong series of events celebrating the Western way of life that is synonymous with the town’s identity. Alongside the rodeo’s competitions, festivities include a parade; a dinner and dance; and a Stampede Street Party that features live music, food vendors and a cattle drive, where dozens of cattle are herded down Main Street.
“The rodeo is the major event in Prineville, period,” Judy says. “We’re the Cowboy Capital of Oregon, and the people of Prineville are very proud of that.”
The oldest incorporated city in Central Oregon, Prineville’s initial growth was driven by ranching, which is why it’s known for its cowboys. In the early 1900s, ranch hands and cowboys who worked the open range came together to wrangle their cattle and separate them before winter. These activities laid the groundwork for what became the Crooked River Roundup, which was first officially held in 1945.
You’ll find that many of the competitions that make up a rodeo are steeped in ranching traditions. Roping events — where competitors race the clock to rope calves — stem from the need to recover wandering livestock or immobilize a calf for branding or veterinary treatment on a working ranch. Bronc riding, in which competitors are scored for riding a bucking horse, gets its roots from taming wild horses on the frontier.
In the three main rodeo roughstock events — bareback riding, saddle bronc riding and bull riding — the animals receive scores for their speed, power and agility. According to Steve, there is as much respect for the animals as the athletes.
“The sheer grit and sheer talent is pretty incredible,” he says. “The crowds come alive.”
Keeping the Rodeo Legacy in the Family
Like his parents, Steve Holliday grew up at the Crook County Fairgrounds, where the rodeo takes place, spending his youngest years ushering people to their seats and helping beautify the grounds by painting fences.
Many years later, when he took his turn as president, he added events to the rodeo that have brought new demographics into the arena. This includes a legacy rider event — where athletes who have aged out of the sport get a chance to compete — and another for youngsters, in which contestants as young as 6 get to try their hand at roping calves.
“The cowboys just love it and the kids get to compete next to their heroes, some of whom are world champions,” Steve says.
“I think the crowd might love [the kids] more than the actual contestants,” Steve’s daughter Corley chimes in. “The crowd sees what they’re doing and are truly impressed. And for the kids, that’s something they’ll carry with them forever.”
Steve and other rodeo leaders have strived to keep the Crooked River Roundup a “cowboy’s rodeo.” That means striking a delicate balance between sports and entertainment, ensuring the event isn’t too flashy and disconnected from its roots but also helping newcomers feel welcome to attend and cheer along. From the grand entry serpentine — where rodeo queens and contestants carry flags in a dazzling opening procession — to the last raucous bull ride, Steve says the roundup has something for everyone.
“I love the pomp and circumstance, but I love seeing a bucking horse too,” he says.
Gaining a Rodeo Royalty Point of View
Part of a rodeo’s pageantry comes from its rodeo queens, ambassadors of the sport known for their rhinestones, tassels and cascading curls. But these polished young women are more than smiling faces; they’re skilled equestrians who promote the rodeo and Western lifestyle at community events.
Corley Holliday grew up with a love for barrel racing, where horseriders race the clock to be the fastest to finish a clover leaf around three barrels. But during her senior year of high school, she decided to expand her horizons and competed for the 2025 Crooked River Roundup Rodeo Queen, a title she won.
As queen, her job is to be the face of the event, or as she says, “spread the word, invite people to the events, answer questions they have.”
Though she’s now in college out of state, Corley plans to return to the Crooked River Roundup each summer. Beyond her family’s strong connection to the rodeo, she says there’s something special about her hometown that she hopes others get to experience when they visit Prineville.
“I’ve really been able to better understand the values my community holds,” she says, “and that is definitely something I want to share with others.”
Where to Stay and Dine in Prineville
There are plenty of food vendors outside the arena, so plan to grab a bite between rodeo events, but be sure to be in your seat for one of the Holliday family’s favorite events, bronc riding. Outside of the rodeo, plan to attend the cattle drive — an event unique to Prineville — or a nightly barn dance.
When visiting Prineville for the Crooked River Roundup, give yourself enough time to see all the town has to offer. Plan to stay a night or two at one of Prineville’s centrally located hotels: High Desert Inn, Best Western Prineville or Country Inn & Suites.
Start your day with a hearty breakfast at Crossroads BBQ Pit & Pub, with menu favorites such as the cowboy stacker — biscuits, sausage, egg and gravy atop a bed of hash browns. Take a break and sip a pint of regionally brewed beer at Wild Ride Brew Co., which has ample outdoor seating at its family-friendly location.
Outside of the rodeo, explore Prineville’s outdoor scene by hiking Chimney Rock Trail to stunning views of the Crooked River and namesake basalt formation. If you need to cool off, jump into the water at Prineville Reservoir State Park, which is also an excellent stargazing location and Oregon’s first International Dark Sky Park.
