Derby Day Beyond Churchill Downs

At JCT. Kitchen & Bar it’s all about the food—sample Kentucky Hot Brown biscuits, Bulleit bourbon—glazed ribs with heirloom tomato and mint salad, pimento cheese and pickled cucumber tea sandwiches, and salted caramel banana pudding. Sip hand-mixed Kentucky 75s, made with bourbon instead of gin, while you pull for that dark horse contender.

Each of the past nine Kentucky Derby winners can trace its bloodlines back to Belle Meade Plantation, making the farm a more-than-appropriate spot to cheer on this year’s champ. Swing a croquet mallet on one of the mansion’s new lawn-game courts to work up an appetite. Then dig in to the traditional bluegrass buffet while big-screen televisions broadcast the gallop to the finish line.

A decade ago, three homesick Southerners threw a Derby bash in a New York City apartment. Today the Brooklyn Derby packs the 13,000-square-foot Greenwood Park beer garden in Park Slope, which is converted to a bourbon lover’s paradise for an afternoon of tricycle races, cornhole, live bluegrass music, big hats, and an even bigger time.

Keeneland employs more than a thousand televisions and drive-through wagering lanes to host the world’s biggest Derby party—outside of the actual Derby, that is. And it doesn’t disappoint. If it’s warm, head to the open-air Keene Barn for live music and snacks. Or don your best Derby duds and reserve a coveted spot in one of the track’s fine-dining rooms.

At the Willard InterContinental‘s annual Derby Day soiree, Bonnets & Bowties, in the historic Round Robin Bar, folks really dress to impress—seersucker to sundresses, fedoras to fascinators. The most dapper guys and gals in the crowd will take home prizes of their own. For the VIP experience, reserve a private table for ten friends and you won’t have to wait in line for one of the bar’s storied Henry Clay mint juleps.