Scenes from the 18th annual 'Brooklyn Derby'

Some 300 people gathered in Greenwood Park on a damp Derby day for extravagant hats, lots of bourbon—and two minutes of racing

By Scott Lynch

It started in a tiny apartment in the East Village some 19 years ago, when three roommates threw a Kentucky Derby party. They made overly elaborate hats together, placed some friendly bets, and drank many, many mint juleps.

Nothing that unusual; people throw fun parties in tiny apartments all the time. But Jessi Arrington and Creigton Mershon, from Mississippi and Louisville respectively (they now live together in Bed-Stuy), turned this small, private affair into an annual public event, the Brooklyn Derby, which in pre-pandemic times had become the borough’s fan favorite, attracting more than 500 dudded-up revelers to drink the day away at the South Slope beergarden Greenwood Park.

Brooklyn Derby co-founders and hosts, Creighton Mershon and Jessi Arington (Scott Lynch)

Original roomie Josh Stewart and co-host-since-2012 Casson Rosenblatt have also played key roles through the years to keep the festivities going.

Covid canceled the Kentucky Derby in 2020, and, according to Arrington, last year’s Brooklyn Derby at Greenwood Park “was a very tame version where everybody had to stay seated at their table.” And although the weather didn’t cooperate this Saturday, the Brooklyn Derby was back in full swing once again, with two live bands, lots of hats, massive amounts of Maker’s Mark, which sponsored the affair, and about 300 people screaming at horses on TV for two minutes before getting back to partying.

“I come to it almost every year,” Shari Jayabose of Park Slope told Brooklyn Magazine. “This is like Carnival for me, because I’m from Trinidad, and we like doing anything to spice things up. This is just me being fun.” When asked about her, uh, festively decorated hat, she told us: “I have no idea what’s going on with my hat. It’s just horses and trophies and numbers and roses.”

In addition to drinking and feasting on notably good “Southern snacks” courtesy of the Greenwood Park kitchen staff (the mini pulled-pork sandwiches, the black-eyed peas, the mac-n-cheese, the pimento cheese, and the cornbread were all first-rate), there was a hat fashion show/contest, and two-buck betting on the big race.

To that end, only 11 people put their money on the long shot winner Rich Strike, splitting the party’s $1,025 pot.

At the make-your-own-hat station (Scott Lynch)

“It feels really good to be back,” Arrington told Brooklyn Magazine about halfway through the party. “And if anybody walks away with one overall feeling I hope that it’s inclusivity. I want Brooklyners to feel like they can come here and just be embraced and loved, and looking around at everybody’s faces it seems like that’s how it’s feeling … Live every day like the first Saturday in May.”

Here are a few more scenes from Brooklyn Derby 2022.