South Philly to celebrate the Kentucky Derby

Can’t get to Churchill Downs for the big race? South Street has you covered.

The Twisted Tail, the popular Southern-inspired restaurant, bar and live Blues joint, will take over the Headhouse Square Plaza on May 6 for a Kentucky Derby Party.

Festivities begin at 11 a.m. and trot through 7 p.m. leading up to the most exciting two minutes in sports.

The all-day street festival will feature a robust live music lineup, a Maker’s Mark Mint Julep Tent, lawn games, best-dressed contests, a jumbotron screen, raffles, giveaways and much more.

The Twisted Tail, located at 509 S. 2nd St., will take over Headhouse Square for the entire day, filling the historic plaza with Derby-inspired food and drink. Attendees are encouraged to arrive in their best Derby outfits as The Twisted Tail will host a Best Ladies Hat competition for ladies and a Most Dapper Gent competition for gentlemen. Live music starts at noon. Attendees can submit for a raffle for the winning horse draw with a chance to win various prizes.

“We’re beyond excited to be back with our full Derby Day celebration this year, and it’s going to be bigger than ever,” said George Reilly, owner of The Twisted Tail. “Thanks to Levante Brewing and Beam Suntory, we’re pulling out all the stops.”

A dedicated Makers Mark Mint Julep Tent will serve freshly mixed juleps while the outdoor bar serves up traditional, watermelon and grilled pineapple Hornitos Margaritas as well as draft pours of Cumbersome IPA and Escalante Mexican-style lager by Levante Brewing Company. The Twisted Tail Outdoor Grill Tent will be serving up sizzling BBQ favorites with a twist, including Chicken Skewers, BBQ Glazed Meatballs, cheeseburgers, Kobe Beef Hot Dogs with bacon jam and Chorizo Tacos.

Music acts include local blues legends Shakey Lee, Brad & Margie, Tom Craig Band, Collin Bunch Band and Gypsy Joe Alves & the Groove Prophets.

Inside the restaurant, in lieu of brunch, the Twisted Tail will be bringing back a special What’s the Catch? menu, originally introduced by Reilly during the pandemic as an homage to his British roots. The menu will center around crowd-favorite Fish n’ Chips with a choice of cod, haddock or the catch of the day. 

Seating is first come, first served, and there will be no reservations.