Grand Marshals - Chuck & Judy Holliday

Introducing the Roundup's 2025 Grand Marshals

Both raised in Prineville and graduates of Crook County High School, Chuck and Judy Holliday were married in 1968. They moved away to start their family and careers but returned to Prineville in 1984 to finish raising their family and careers closer to their roots. Chuck was a teacher and wrestling coach, completing his 30-year career with the Crook County School District. Judy worked for U.S. Bank, retiring after 28 years.
Chuck’s first memory of the Roundup was after his family moved to Prineville in 1946 when he was three years old. His mom bought each of the kids a new bandana to wear to the rodeo, and they were beyond excited to go! Judy had a little cowgirl outfit that she wore to watch the parade and then to attend the rodeo. Her favorite part was—and still is—the Grand Entry, with all the pageantry and the queens.
They have two amazing kids, both successful business owners in Prineville, who continue to give back to the community in various ways. Steve, the previous owner of Prineville Disposal, is currently the President of the Roundup, serving his third year in that role. Michelle, who owns The Posie Shoppe, was a court representative for the Roundup in 1991, the Sisters Rodeo Queen in 1992, and went on to become Miss Rodeo Oregon in 1993.
Chuck joined the board of directors in 1990 and was chosen Hardest Working Board Member in 1991, later elected President in 1993. He took over the vendor program, transforming it from a single vendor into a variety of food and merchandise vendors. He also introduced the “beer chit” system at the beer booth, which made serving beer more efficient. Chuck was instrumental in shaping the cattle drive we still see today; while the route was different, it remains an event everyone looks forward to each year. The large “Crooked River Roundup” metal letters on the backside of the grandstand were one of the projects he is most proud of.
Judy joined the Board of Directors in 1989 and received the Hardest Working Board Member award in 1992. She and her sister, Donna, were in charge of the Roundup Court during her time on the board. During her tenure, the Queen’s program was changed to feature a single representative queen.
Judy took the reins by establishing the Hoopla Committee, and the Dusty Chaps Gang, along with their accompanying Floozies, were brought to life. They were responsible for “robbing” the Dinner Train that was active at that time and even set up a full western scene in the center of town, complete with a livery stable, jail, and bank. Desperados (board members Pat McCabe and Larry Koops) robbed the bank and were captured by the law (board members on horseback) before being tossed in jail! Both events were covered by the Bend Bulletin and made the front page.
Judy and her daughter, Michelle, also ran the Miss Rodeo Oregon Pageant, which was held in Prineville for two years.
Both Chuck and Judy continue to support the Roundup in some capacity every year and are excited to see the growth that has taken place, making it one of the premier events in Central Oregon every summer, with rodeo and horse racing.
“We are so honored to have been chosen as Grand Marshals for 2025 and invite all to join us in June and July for rodeo and horse racing in the Cowboy Capital of Oregon.”

CRR Flashback

Did you know? In 1982, when Bill Steelhammer resigned from the board, Alvin Grimes nominated Berna (Bill’s wife) to replace him while at the annual stockholders meeting. Berna became the first female member, and they also became the first husband-and-wife team to be honored as Grand Marshals of the parade.