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Derby Day Philly Style: The Twisted Tail Takes Over Headhouse Square

Brenda Hillegas
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PHILADELPHIA, PA - Get ready to don your finest hats and celebrate "the most exciting two minutes in sports" right here in Philadelphia! The Twisted Tail, the popular Southern-inspired restaurant, bar, and live Blues joint, is hosting its annual, blowout Kentucky Derby Party and street festival. On Saturday, May 3, 2025, from 12:00 PM to 7:00 PM, historic Headhouse Square Plaza will transform into a Derby Day destination, filled with live music, delicious food, refreshing drinks, lawn games, and, of course, prime viewing of the big race.


Photo by Shelby Ricci/Reel Media
Photo by Shelby Ricci/Reel Media

The Ultimate Derby Street Festival Experience

The Twisted Tail is bringing the spirit of Churchill Downs to Headhouse Square for an all-day celebration, sponsored by Beam Suntory. Here's what attendees can expect:

Sipping on Derby Delights

No Kentucky Derby party is complete without the signature drink.

Sizzling Southern Flavors

The Twisted Tail Outdoor Grill Tent will be serving up a menu of BBQ favorites with a Southern twist:

Elevate Your Experience: The VIP Option

For those seeking an extra touch of extravagance, a limited number of VIP tickets are available for $50. This exclusive experience takes place in The Twisted Tail's second-floor Club Room and includes:

VIP tickets can be purchased online at: [Link to purchase VIP tickets - replace with actual link from aidsfundphilly dot org/gaybingo as per the (likely erroneous) press release context, or ideally, find the correct link via Twisted Tail/Eventbrite] (Note: The provided link seems incorrect for this event, verify the correct purchase link)

Party Continues Inside

The celebration doesn't end with the race! The full Twisted Tail menu will be available inside the restaurant (509 S. 2nd St.) all day long. As the sun sets, the party moves indoors with live music continuing in the Juke Joint upstairs. Seating inside is first come, first served (no reservations).


"We’re stepping up our Derby Day celebration this year with even more fun and excitement," said George Reilly, owner of The Twisted Tail. From the festive street party atmosphere in Headhouse Square to the delicious food, classic Mint Juleps, live music, and exciting VIP options, The Twisted Tail's Kentucky Derby Party is the place to be in Philadelphia on May 3rd. It's free to attend the outdoor festival, so grab your best hat and get ready to celebrate the Run for the Roses Philly style!