My Derby Diary

LOUISVILLE, Kentucky – What's it like to be at the races? We got the play-by-play from David McGuire, the former director of the Kentucky Museum of Art and Craft and now investor in soon-to-open St. Charles Exchange restaurant.

Thursday, May 4: Get Set

Peruse various shops looking for my Derby accessories, i.e. hat. The Kentucky Museum of Art and Craft gallery is featuring the fine milliner work of Sara Havens. I may buy a hat here or at least a great local jewel. That night, I'll have dinner at Jack Fry's before the rush.

Friday, May 4: Oaks Day

I'll attend the 26th annual KMAC Oaks Brunch at the historic Brown Hotel, which kicks off at 9 a.m. While sipping mimosas, I'll probably probably bid on some great art work — maybe buy another hat, then EAT. After brunch, Churchill Downs with my partner, Shawn Hadley. If the Derby is known as the Run for the Roses, Kentucky Oaks the day before is the Lilies for the Fillies. Lots of lilies will be consumed ("lilies," in this case, meaning cocktails with vodka, cranberry, and something else...maybe club soda?). After the race, a car ride to Buck's. Great old-school place in old Louisville. Buck will be there. Dinner, drinks, finally home!

Saturday, May 5: The Derby

It starts with mimosas and appetizers from The Cheddar Box at a private home. Will take my time this year, as the race is fairly late.

Arrive at Churchill by 3 p.m. and head to second-floor clubhouse box owned by my dear friends and business partners Amy and Rob Frey. Walk around, passes in tow, i.e. full access to The Downs.

Juleps and betting for 3+ hours. Then the race!!!!

Cash out and head to the car.

Dinner at our new place, St. Charles Exchange, which opens officially at the end of May but is in soft opening, especially for special occasions like this. I'll nod hello to everyone celebrating along the 34-foot bar.

Cross the street and work the room at 21C's private Derby party, which usually becomes free to public around 11 p.m. (Wink-wink.)

Now I'm really tired. Car home to the farm. I'm drunk, and it's over.

READ MORE ON FATHOM

Little Black Book: The Master Blender's Derby Circuit
Kentucky Derby: Lexington Essentials

MORE RACING AND GAMBLING

A Day at the Races in Windsor 
The Coronation Stakes at the Royal Ascot