Derby Weekend in Downtown Lexington

By Emma Buchanan

The 147th Kentucky Derby takes place this Saturday, May 1st and we could not be more excited! We’re optimistic for beautiful weather and it’s a great excuse to dress up, have a few fancy drinks and cheer on Kentucky’s grandest tradition. We’ll be staying in Lexington this year, so while we can’t watch the race at the historic Churchill Downs, we have come up with a list of ways to make your Derby experience as much fun as possible in #downtownlex!

Places To Go

The Horse and Jockey

Relax and enjoy the Derby on one of Downtown Lexington’s finest patios, The Horse and Jockey Pub. On Saturday they will be serving brunch from 11 am-3 pm, including bottomless mimosas. If you decide to stay for dinner, they have amazing jockey wings that are sure to hit the spot!


Celebrate the Kentucky Derby at Keeneland, the home of horse racing in Lexington! With over 1,000 TVs, access to live wagering, great food, and live music, Keeneland is the perfect place to watch the Run for the Roses. Click here to purchase tickets for the event.

Jeff Ruby’s

Enjoy Kentucky’s oldest tradition at one of Kentucky’s finest restaurants. Derby Day will be a beautiful day to dine on Jeff Ruby’s patio. Treat yourself to USDA Prime Steaks, an award-winning wine list, and impeccable service.

Belle’s Cocktail House

Belle’s Cocktail House is a 3-story bar that’s having its grand reopening this weekend, just in time to celebrate Oaks and Derby Weekend! Make sure to get to Belle’s early because it’s going to be a packed house!

Staying In

If you’re looking to host a Derby or Oaks party at your house, we’ve got you covered. Impress your guests with catering from Tony’s Steak and Seafood, a Lexington favorite who have a fantastic variety of takeout options that are sure to leave you and your guests satisfied!

Another excellent carryout option is Pasta Garage, who has an extensive catering menu with delicious pasta that makes serving a breeze! Click here to see their catering menu and get your order ready!

You can also bring the Jeff Ruby Experience to your home with their meal kits, available for carryout or delivery! Wow your guests with a fantastic meal in your own home! Click here to check out your options!

Whichever you choose, these #downtownlex restaurants will be a perfect addition to your gathering!

You can watch the races on TV on Oaks Day (Friday) on NBCSN from noon to 6 pm and on Derby Day (Saturday) on NBCSN and NBC from noon to 2:30 pm and 2:30 pm to 7:30 pm.

Derby Drink Recipes

The following are some of our favorite Derby cocktail recipes you can try out this year! All recipe links also include mocktail versions. (Click here for a full list from the Kentucky Derby website.)

DLP Staff Picks

(NOTE: We know very little about horse racing, this is just for fun! Please gamble responsibly! All odds were correct at the time of posting on April 28, 2021.)

  • Terry Sweeney: Rock Your World (5-1)
  • Laura Farnsworth: Soup and Sandwich (30-1)
  • Taylor McDonald: Midnight Bourbon (20-1)
  • Harrison Stiles: Medina Spirit (15-1)

For a live list of all the horses and their odds, click here!


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