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Kentucky Oaks brings out ‘pinch me’ moments for Churchill Downs crowd

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Heading into Kentucky Derby Weekend, William and Dorothy Kania made the trip to Louisville from Northern Indiana with a plan.

They made the nearly five-hour trip from around Gary to the Wyndham East in Jeffersontown on April 30 and had burgers at Brass Social — “it was fantastic,” William Kania said in a May 1 interview at Churchill Downs. After that, it was time to rest up and get ready for a weekend at the races.

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“Don’t be afraid to bet horses that ran good in their last race,” he advised first-timers. “The true handicappers will say, ‘Oh, that’s too easy.’ The horses that run good, they keep running good.”

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The couple had their eye on Percy’s Bar in the Kentucky Oaks, the annual showcase for fillies run the day before the Kentucky Derby that was set to take place later that evening. A full card of 13 races was scheduled throughout the day, with the Oaks set to cap off the night at 8:40 p.m.

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Kentucky Oaks 2026 fashion, fans and fun at Churchill Downs

Whitney Ensor kisses her husband Howard Ensor while attending the 152nd running of the Kentucky Oaks at Churchill Downs on Friday, May 1, 2026. The Ensor’s got engaged at the Kentucky Derby.

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Oaks Day, which takes steps to recognize breast and ovarian cancer survivors, always brings a pink-filled crowd to Churchill Downs. There were 100,910 attendees in 2025 and 107,236 in attendance the year before.

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The 2026 forecast was cooler than usual, with temperatures not expected to rise past the low 60s, but rain was not expected. The forecast for the May 2 Kentucky Derby is similar, with temperatures not likely to rise past the upper 50s.

It’s a little chillier than the weather in Central Florida, where Johnna and Payne Luce live. The couple took photos outside Churchill Downs around noon on May 1 as they worked through the crowd to enter the racetrack.

They’re here for the weekend, shelling out for all-inclusive tickets in the Ford First Turn reserved section. Johnna said it’ll probably be the only time they make the trip, so they wanted the full experience. She didn’t grow up around horses but would watch the Kentucky Derby every year with her grandma — “I’ve watched it ever since I was little and I love it.”

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Kentucky Derby 2026 fashion was bold, head-turning and chic. See photos

Fashion during Thurby at Churchill Downs during 152nd Kentucky Derby, Louisville, KY. April 30, 2026 (by Frankie Steele/Special to Courier Journal)

“This has always been her dream,” Payne Luce said. “She and her grandmother have shared a special bond over the Kentucky Derby.”

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Deb Woodcock also grew up watching the race. When she was young, she said, she wanted to be a Derby jockey when she was older.

“I had the height thing going,” she said with a laugh. “I love horses. I just love them.”

That particular dream may not have come to fruition, but Woodcook finally made it to the Derby this year in celebration of her 70th birthday. Her son, Eric Vavasek, surprised her with the trip from New York to Louisville for Woodcook’s milestone birthday.

“She doesn’t really watch a lot of live sporting events, but she never misses the Derby,” Vavasek told The Courier Journal. “To be able to do something for her that I know she’s really wanted to do just makes it extra special.”

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When Woodcook found out about the gift, she started crying.

“I couldn’t believe it,” she said. “ I still can’t believe it.”

Sipping on an Oaks Lily and snacking on mac-and-cheese bites, Woodcook wore a long pink dress peppered with black flowers and a matching floppy hat, decorated with a lily.

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“Being here, it’s amazing,” she said of the “pinch me” day. “I don’t even have the words and I haven’t even seen the horses yet.”

Dressed in a long light pink cape, Linda Bonilla from West Palm Beach, Florida, said her look was inspired by “ballerina vibes” and staying warm. And Carrie Sweet, from Northern California, was dressed in pink polka dots with a scene from “Pretty Woman,” featuring superstar Julia Roberts, in mind.

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Sweet, who chose to celebrate her upcoming 60th birthday with a trip to the Kentucky Oaks, said her dress “just spoke to me.”

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“It’s just the best sporting event,” Sweet said. “The people watching, the drinks, the whole vibe is so much fun.”

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See the best 2026 Kentucky Derby hats, fascinators inside Churchill Downs

Ashlyn Roberts enjoys a mint julep on Thurby during Kentucky Derby week at Churchill Downs in Louisville, Ky., on April 30, 2026.

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Always scheduled for the first Saturday in May, this year’s Kentucky Derby is set for May 2 at Churchill Downs. Gates at the famed Louisville racetrack open at 8 a.m. while the first race’s post time is set for 11 a.m. The Derby, which will air on NBC, should start at 6:57 p.m.

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Reach Amanda Hancock at ahancock@courier-journal.com. Reach Lucas Aulbach at laulbach@courier-journal.com.

This article originally appeared on Louisville Courier Journal: Kentucky Oaks brings crowd to Churchill Downs for Derby Weekend

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