The Twisted Tail’s Kentucky Derby Party Returns to Headhouse Square With Live Music, Mint Juleps, and Best-Dressed Contests
The Twisted Tail’s Kentucky Derby Party Returns to Headhouse Square With Live Music, Mint Juleps, and Best-Dressed Contests
One of Philly’s most festive Derby Day traditions is back as The Twisted Tail brings its annual Kentucky Derby Party to Headhouse Square on Saturday, May 2, from 12 p.m. to 7 p.m.
The all-day outdoor celebration transforms the plaza into a lively Southern-inspired street festival, complete with live music, food and drink tents, lawn games, and a large screen for watching the race. Tickets are available on Eventbrite.
The party kicks off at noon with live music setting the tone throughout the afternoon. Guests can enjoy performances from local acts including:
- Judd Nielsen & Mikey Junior
- Shakey Lyman
- Brad Vickers & Margie Peters
- Midnight Dispatch
- Gypsy Joe Alves & the Groove Prophets
Race coverage begins at 6 p.m., leading up to the main event just before 7 p.m., followed by a winner’s circle celebration.
No Derby party is complete without a signature drink, and guests can sip on freshly made Mint Juleps from the cocktail tent—each one coming with a raffle entry.
The outdoor grill will be serving up crowd favorites like burgers, hot dogs, tacos, and corn, while lawn games and interactive activities keep the energy high throughout the day.
Attendees can also take part in a “Pick the Winning Horse” contest for a chance to win prizes.
Derby style is highly encouraged, with a best-dressed competition adding to the experience. From bold hats to colorful suits and dresses, the event invites guests to fully embrace the spirit of the Kentucky Derby.
For those looking to upgrade their day, a VIP Experience inside The Twisted Tail’s second-floor Club Room offers:
- DIY flower crown and pocket square station
- Commemorative julep cup
- Complimentary Mint Julep (with raffle entry)
- Whiskey tastings from 1 p.m. to 5 p.m.
- Unlimited draft beer
- Keepsake beer mug
- Private indoor and outdoor viewing areas
VIP tickets are priced at $100.
Keep the Party Going
While the outdoor festivities wrap up in the early evening, the celebration continues inside the venue, where live music will carry on in the upstairs Juke Joint. The full restaurant menu will also be available throughout the day.
