Kentucky Derby Day in Philly at The Twisted Tail
Philadelphia embraces Southern charm with The Twisted Tail’s epic street festival, celebrating the 151st Kentucky Derby. Taking place at the historic Headhouse Square Plaza on Saturday, May 3, from noon to 7 pm, this spirited celebration promises a spectacular day filled with vibrant music, delectable Derby-inspired cuisine, and refreshing cocktails, capturing the timeless elegance and excitement of the legendary horse race.
You will be immersed in the authentic Derby spirit, sipping classic Maker’s Mark Mint Juleps beneath a dedicated bourbon tent. Each julep comes with a raffle ticket, offering lucky attendees a chance to win fantastic prizes. Also featured are refreshing Hornitos Margaritas, Spiked Lemonades, and ice-cold draft beers. Culinary offerings at The Twisted Tail outdoor grill tent promise bold, mouth-watering flavors. Highlights include Chicken Skewers, BBQ Glazed Meatballs, juicy Cheeseburgers, Kobe Beef Hot Dogs topped with savory Bacon Jam, Chorizo Tacos, and succulent Pork Belly Sliders.
For those seeking an elevated experience, VIP tickets provide exclusive access to the luxurious second-floor Club Room. Guests can craft their own flower crowns, enjoy Maker’s Mark tastings, and receive commemorative julep cups along with Derby Day swag. Live music from celebrated local blues and rock artists, headlined by the renowned Mikey Jr., will electrify the plaza from noon to 6 pm. And, of course, Derby tradition calls for stylish attire—prepare your finest hats and dapper outfits, as The Twisted Tail hosts Best Ladies Hat and Most Dapper Gent contests.
After sunset, the festivities move indoors, where the full Twisted Tail menu awaits guests alongside more live entertainment, ensuring the celebration continues long after the final race.
More Kentucky Derby Day Celebrations in Philly
Beyond Headhouse Square, Philadelphia offers several enticing options to celebrate Kentucky Derby Day in exceptional style. At Parx Casino in Bensalem, guests can savor a thrilling live thoroughbred racing experience paired with family-friendly entertainment, including pony rides, moon bounces, and face painters. Live music, food specials, and giant screens showcasing the Derby make this an ideal family-oriented celebration.
In Old City, PJ Clarke’s Philadelphia at The Curtis Building brings a refined yet lively Kentucky Derby party. Expect gourmet Derby-themed delights, from savory Pimento Cheese Toast and Kentucky Pecan Pie Empanadas to Knife-and-Fork Ribs and zesty Hushpuppies served with Cilantro Jalapeno Aioli. Classic cocktails, including Mint Juleps and Kentucky Mules, complement the sophisticated atmosphere at the grand wooden bar surrounded by red leather stools and vintage decor—ideal for Derby enthusiasts who appreciate elegance and tradition.
Over at Yards Brewing on Spring Garden, a Derby viewing party combines craft beer specials, including their popular Pynk ale and unique bourbon-infused cocktails like the Kentucky Mule and “Buck Around and Find Out” (bourbon, ginger ale, strawberry). Gourmet selections such as the Original Kentucky Derby Fried Chicken Sandwich and a sumptuous Bourbon Smash Burger round out this vibrant gathering. Guests will have additional excitement as tables are randomly assigned horses, with potential bill discounts for the winning table.
Brauhaus Schmitz blends cultures with its South Street Maifest event. Amid Philly’s largest German spring festival, Derby fans can slip indoors to catch live Kentucky Derby action on multiple screens, perfectly blending traditional German festivities with the timeless American charm of Derby Day.
Whichever venue you choose, all bets are covered for unforgettable experiences to celebrate the excitement, elegance, and tradition of the Kentucky Derby in 2025.
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