Kentucky Derby in and around Philly
The Kentucky Derby is more than just a horse race—it’s an event steeped in tradition, style, and celebration. Whether you’re attending an elegant fundraiser in Radnor, a lively rooftop party in Philly, or a vineyard gathering at Chaddsford Winery or Penns Woods Winery, there are plenty of ways to embrace the spirit of the Run for the Roses in style.
From breathtaking fashion to bourbon-infused cocktails, here’s your ultimate guide to making the most of Derby Day in and around Philly.
Where to Celebrate Derby Day Near Philly
With so many unique events happening, you don’t have to travel to Churchill Downs to soak in the excitement. Whether you’re looking for an upscale soirée, a lively outdoor bash, or a vineyard experience, there’s something for everyone.
The Twisted Tail’s Derby Day Festival
This festival transforms Headhouse Square Plaza into a full-fledged Derby experience with live music, bourbon tastings, and a Best Hat contest. Expect craft cocktails, Southern-style bites, and even a flower crown station to add a fresh spring touch to your outfit.
Location: Headhouse Square, Philly
Time: May 3, 2025, 2:00 PM – 7:00 PM
Tickets: Free admission, VIP tickets available
Sunset Social’s 7th Annual Derby Party
If rooftop views and Derby fashion sound like your vibe, Sunset Social’s party is one to check out. With big-screen race viewing, themed cocktails, and fashion contests, it’s a perfect spot for indulging in the Derby spirit.
Location: Sunset Social, Philly
Time: May 3, 2025, 3:00 PM – 8:00 PM
Tickets: Free admission
Parx Casino Derby Celebration
Want to witness real-life horse racing while celebrating the Derby? Parx Casino offers a chance to see live thoroughbred racing, while also hosting pony rides, moon bounces, and family-friendly entertainment.
Location: Parx Casino, Bensalem
Time: May 3, 2025, 12:00 PM – 6:00 PM
Tickets: Free admission
Radnor Educational Foundation Kentucky Derby Fundraiser
Radnor’s Triple Crown Restaurant inside the Radnor Hotel will host an exclusive fundraising event filled with cocktails, live entertainment, light bites, and both silent and live auctions. A perfect opportunity to dress up, sip on a mint julep, and give back to the community.
Location: Triple Crown Restaurant, Radnor Hotel
Time: May 3, 2025, 6:30 PM – 10:30 PM
Tickets: $150
Derby at the Vineyard – Penns Woods Winery
Penns Woods Winery is hosting a spectacular horse jumping event in the vineyard, complete with wine, local beer and cider, live music on the lawn, food trucks, and an artisan market.
Location: Penns Woods Winery, Chadds Ford
Time: May 17-18th
Tickets: Check winery website for details
Derby @ the Vineyard – Chaddsford Winery
Chaddsford Winery is known for its laid-back yet elegant atmosphere, and this year’s Derby celebration will feature wine tastings, live entertainment, and a relaxed vineyard setting.
Location: Chaddsford Winery, Chadds Ford
Time: May 3rd, 2025
Tickets: Check winery website for details
Harrah’s Casino
Harrah’s Philadelphia is excited to present this year’s Delaware County’s largest Derby Day Watch Party at the Racetrack. On Saturday, May 3rd, beginning at 2:00 PM, the Philadelphia & Chester community is invited to partake in a festive Derby Day celebration. The day will feature continuous musical entertainment from KISS 101.7 and engaging yard games available in the Beer Garden. We encourage all members of the public to join us for this exciting event.
Attendees are encouraged to wear their best hats and sign up for the Derby Hat Contest. A player card is required to sign up. Registration opens at 2:00 PM and the contest kicks off at 4:30 PM. Drawings will be held from 3:00 PM to 4:00 PM and again from 5:30 PM, or as soon as the hat contest concludes, until 6:00 PM, with 20 winners selected every 30 minutes.
Get more information!
Must-Try Derby Cocktails
Nothing pairs better with a day at the races than a well-crafted bourbon cocktail. Whether you’re hosting a party or just looking for an excuse to shake up something fancy, these Derby-inspired drinks will set the mood.
Classic Mint Julep
A Kentucky Derby staple, simple yet refreshing.
Ingredients:
- 5 fresh mint leaves
- ½ oz simple syrup
- 2 oz bourbon
- Crushed ice
- Garnish: Mint sprig
How to Make It:
Muddle the mint leaves with simple syrup, add bourbon, and fill the glass with crushed ice. Stir gently and top with a mint sprig.
Blackberry Mint Julep
A fresh twist with bold berry flavors.
Ingredients:
- 2 oz bourbon
- Handful of blackberries
- 5 mint leaves
- ½ oz sugar
- Splash of water
- Crushed ice
How to Make It:
Muddle blackberries, mint, sugar, and water in a glass. Add bourbon and crushed ice, then stir well. Garnish with mint and a few extra berries.
Kentucky Mule
A Derby-inspired version of the Moscow Mule.
Ingredients:
- 2 oz bourbon
- ½ oz lime juice
- Ginger beer
- Ice
- Lime wedge for garnish
How to Make It:
Pour bourbon and lime juice over ice, top with ginger beer, and stir. Garnish with a lime wedge.
Derby Fashion: Dos & Don’ts
Derby fashion is bold, classic, and elegant, with an emphasis on statement pieces and polished details. Here’s how to nail the look for any Derby celebration.
Dos:
Statement Hats & Fascinators – The bigger, the better! Floral embellishments, pastel tones, and dramatic silhouettes make the perfect Derby look.
Elegant Attire – For women, think floral dresses or jumpsuits; for men, tailored blazers, linen suits, or polo shirts.
Comfortable Shoes – You’ll be on your feet for hours, so opt for stylish wedges, kitten heels, or classy loafers.
Don’ts:
Jeans & Sneakers – The Derby is not a casual event—no denim, athleisure, or basic sneakers.
Heavy Layers – Spring temperatures vary, so wear breathable fabrics like linen and cotton.
Clashing Colors – Bright colors are encouraged, but be mindful of choosing complementary tones.
Wellness Tips for a Stress-Free Derby Day
With all the excitement, socializing, and cocktails, it’s important to keep your wellness in check. Here are a few simple ways to make sure you enjoy the day without burning out.
Get Ready for an Unforgettable Derby Day
With Derby-inspired cocktails, stunning fashion, and exciting events across Philly, Radnor, Chaddsford, and Penns Woods, you have plenty of ways to celebrate in style. Whether you’re dressing up for a fundraiser or mixing mint juleps at home, embrace the elegance, joy, and Southern charm that make the Kentucky Derby so special.
