PRINEVILLE — The Bend foursome gripped their betting slips waiting for the first race of the 2019 Crooked River Roundup to start.

The odds of winning in the four-horse race were in their favor with wagers placed on one, two and three.

Within minutes, the 250-yard race on the oval track started with a bang.

Mark Zoboski, 68, his wife, Betsy Zoboski, 63, and her sisters, Susan Thomas and Cathy Fowler, hooted and hollered along with the crowd for their horses to win.

The winner: horse No. 4, Eyebrow Pride.

“We’re losers!” Betsy Zoboski joked.

The four-day event, which some Central Oregonians consider a tradition, ends Saturday. Attendees at the first night of the 53rd annual Crooked River Roundup horse races had a variety of reasons for coming, whether it was their first time or 20th. Some loved the thrill of low-stakes gambling, others enjoyed the cowboy culture and sense of community.

For Bend resident Dana Thill, 48, who grew up in Prineville, the horse races are a fun tradition reminiscent of her youth.

“We used to come here to look for boys,” she said, laughing. “It was a small town, not much to do back then.”

After the first race, the country-rap hit “Old Town Road” blared over the speakers, keeping the atmosphere lively while many in the estimated crowd of 4,000 at the Crook County Fairgrounds placed their bets for the second race.

The sounds of squealing children and laughing grown-ups filled the air, along with the familiar smells of sweet and salty fair snacks like shave ice, funnel cake and barbecue.

Katie Howard, 34, brought her husband, Jeff, and three young kids from Seattle for the annual horse races. The children excitedly pointed at every horse that walked by. She grew up in Prineville and went to the horse races many times as a kid. She noted that “the fairgrounds feel the same, but Prineville’s changed.”

“I was mostly not even watching the races and things, but just hanging out with friends,” Howard said, reminiscing on her high school years. “It was something to do in the summer.”

Some teenage visitors already have nostalgia for the Crooked River Roundup.

“I used to come here when I was a kid all the time, and I loved it,” said Ian Kimmel, 18, who was visiting his old hometown from Ohio. “It’s like its own little tradition.”

Many of the attendees from Crook County emphasized how much the roundup meant to the community.

Doug Smith, the event’s director of racing who’s worked with the roundup for nearly four decades, said the horse races, which run from Wednesday to Saturday, bring in tons of money for local businesses.

“You have 250 horses on the ground; those people are buying hay and feed,” he said. “If they break a rope, they’ll buy rope in Prineville. Every hotel is filled to capacity.”

Joe Sherman said he moved to Prineville three years ago to help build the data centers nearby, and couldn’t avoid the roundup hype.

“When I first came here, that’s all I heard about all summer long, was the horse races,” he said.

For Will Dai, a 29-year-old Bend resident who recently moved from Portland, the roundup was a fun excursion. Plus, he had gotten lucky early in the night by winning the trifecta in the second race, meaning he correctly guessed the first, second and third place horses in exact order.

“It’s just cool to watch,” he said. “You don’t see this every day, especially if you’re coming from the city.”

Not all attendees planned on betting Wednesday, but some of those that did had unique strategies or superstitions.

“I like to pick a calm horse if it’s going to be a long run,” said Prineville resident Janice Lockwood, 61. “The giddy ones will burn out in the first 50 yards, and the calm ones are there for the long haul.”

Mark Zoboski picked horse No. 1 in the first race because he usually picked the first horse. Betsy Zoboski chose horse No. 2, because it was gray and she always bets on the gray horse. Fowler, 61, picked horse No. 3 because it’s her lucky number, while Thomas had a family connection to the horse No. 3’s name, Jessadalight.

“My daughter has a really good friend named Jessica, and we always call her Jess,” Thomas said. “I thought it was meant to be.”

Corey Rucker, 30, from Bend, said she likes to bet on horses that look “sassy.”

Prineville resident Luis Rivera, 23, said he only bets on the very last race, for good luck.

“I come here every year; it’s my favorite,” he said. “It has everything I love: horses, racing and a little bit of gambling.”

It’s not just the attendees that love the Crooked River Roundup. Jake Samuels, 26, a jockey who’s raced horses for about nine years, said the Crooked River Roundup was easily his favorite Oregon track, mostly because of the crowd’s passion.

“Crowds here are passionate, bigger, louder … they like to bet the races, they cheer for everybody, it’s pretty neat,” he said. “It’s good to see people get really involved in horse racing.”

— Reporter: 541-617-7854,

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