How to Win Big and Party Hard at the Kentucky Derby

You’ve migrated to Louisville to finally experience the apogee of horse racing (and betting) that is the Kentucky Derby. The late king of Gonzo and Louisvillian Hunter S. Thompson once famously said that you haven’t done the Derby right unless you’re crawling on your hands and knees back to the plane. That might not be what you’re going for. Here are the best ways to celebrate the Run for the Roses.

The races

For those new to the concept, the Kentucky Derby is a set of horse races held annually at the historic Churchill Downs racetrack over the first weekend in May. This year will be the 143rd year of the meets, which consist of close to a dozen races each day. The big race, the Kentucky Derby, known as “The Most Exciting Two Minutes in Sports,” is run on the Saturday. For those looking to relive Thompson’s revelry, try watching the race from the infield — the space inside the track that holds 50,000 people and can resemble something Caligula would be proud of.

Look different

Avoid the predictable seersucker. Finding one that looks different amongst the sea of others is like inventing a new musical note. Instead, opt for something double-breasted, but still light. It gets hot, remember.

Drink right

You’ll be tempted to drink copious amounts of Mint Juleps (when in Louisville, drink as the Louisvillians, is the thinking). Instead check out the Crescent Hill neighbourhood. It has bars on every block stocked with bourbon you won’t find anywhere else. If beer’s your thing, Sergio’s World Beers is a tiny bar offering over 1,000 different beers.

Parties

There will be parties. It should also be noted that Louisville is fast becoming one of the best food towns in the US. For insane tacos try El Camino in the Highlands neighbourhood, and for stellar local Kentucky fare give Ward 426 and Lilly’s Bistro a try. Both are modern, delicious and quintessentially Kentuckian. As for parties, 21c Museum Hotel hosts the most impressive bash, though if you’re able, crash the ultra-exclusive party at The Barnstable Brown. You’ll thank us later.

Betting

As with all things gambling, prepare first to lose money. But how much you lose depends on which betting sage you listen to. The Daily Racing Form is fine, if you can decipher its hieroglyphics. If not, why not check out Jill Byrne, resident announcer and picker for Churchill Downs. She has an impressive track record.

“Thurby” not Derby

If sweating with 150,000 people is not your thing, skip the big day and rock up to Churchill Downs on the Thursday before the big race. It’s the day locals pay pilgrimage to the track and things are a little more civilized in terms of attendance figures. Thursday is the new Saturday round these parts.