- May 7, 2026
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Longboaters broke out the colorful clothes and extravagant hats just in time to celebrate the May 4 running of the 150th Kentucky Derby.
The Observer visited two of the many Kentucky Derby parties on the island to see the festive outfits and tasty food Longboat Key residents enjoyed while watching Mystik Dan (18-1) nose out competitors in a three-way photo finish.
Seaplace Condominiums celebrated the Kentucky Derby for the first time in years. The watch party in the clubhouse drew 90 residents.
For betting, the committee took a different approach. Each bettor received a ticket assigning them a horse at random. This allowed the winning bettor to be chosen by chance.
Kentucky native Penny Gold was in charge of making mint juleps, the signature Kentucky Derby drink. Gold said that her family is from the center of the action for The Derby — Louisville, Kentucky. Her favorite Kentucky Derby was when her sister decided to bet on every horse that had a cat name.
"She is like the biggest cat person I know," said Gold. "She ended up winning $7,000. So, it wasn't a bad strategy."
Betty Lou Miccio made her Kentucky Derby hat. When planning her hat, she couldn’t find the right colored roses that matched her creative vision. Instead, she decided to use pink bath loofahs to make a colorful and unique hat.
“Now I won’t have to buy loofahs for a bit,” said Miccio. “All I have to do is pull them off my Kentucky Derby Hat, so I like that it serves two purposes.”
The Longboat Key Club looks forward every year to making sure its residents have outstanding experiences for the Kentucky Derby. Its party was held bayfront near the tennis courts.
“It is our largest party of the year,” said event manager Stephanie Kaelin-Bare. “It is also our farewell party so we try to make it as fun as possible with great food and entertainment while, of course, enjoying the main event, watching The Derby.”
Live music played while the guests placed their bets. Everyone was dressed in colorful garden dresses and suits. There was a variety of hats: some store-bought and some made by its owners.
This year was the first year that Anne Sears attended the Kentucky Derby Party at the Key Club. She said that she hadn’t been to The Derby itself, but was in Louisville's Kentucky Derby parade when she was in the marching band at her high school.
“We slept in a terrible school bus all the way from Pennsylvania,” said Sears. “But Louisville went all out. The experience of being in the city during one of its biggest events was incredible. It is such a great tradition.”
Brooke Bayo wanted her hat to have a moss theme so she styled patches of fake moss with flowers and ribbon. Her favorite part of The Derby is that it allows her to get creative and think outside the box for these extravagant hats.
Donna Larson attended The Derby multiple times in her life. Her favorite time was when she won $5,000 from betting on the horse whose jockey was wearing her favorite color.
“Don’t listen to any other methods of betting on these races," said Larson. "You just need to look at what the jockeys are wearing and pick the one wearing your favorite color. This is the true key to winning your bets at The Derby.”
