MAXIE'S SOUTHERN COMFORT
Derby Day 2026
🌹 MAXIE'S KENTUCKY COMFORT 🌹
It's Derby Day, Darling.
May 2, 2026 | Maxie's Milwaukee | Hats Strongly Suggested. Good Times Guaranteed.
The roses are red. The bourbon is cold. And Milwaukee's most festive party is galloping back to Maxie's for Derby Day 2026.
Whether you're a die-hard horse racing fan or you just really, really love an excuse to wear a fabulous hat (honestly, same), Derby Day at Maxie's is the place to be on May 2nd. We're talking Mint Juleps, Southern hospitality, the thrill of the race — and a prize package so loaded you'll want to start picking your outfit right now.
👒 Dress to Win — Literally
This isn't your average 'wear whatever' Saturday brunch situation. At Maxie's Derby Day, your look could win you some seriously spectacular prizes. We've got multiple Best Dressed categories — so there's truly a crown for everyone:
- Best Dressed Man: A $100 gift certificate to Skeare Barber Services for a cut and shave. Look sharp.
- Best Dressed Woman: A $100 gift certificate to Roots Salon. Because looking this good deserves a follow-up.
- Most Elegant Hat: A $100 gift certificate to Nourish Spa. Pure luxury.
- Most Creative Hat: A Float MKE gift certificate. Because the most creative minds deserve to float.
- Best Dressed Couple: $100 in gift cards. Date night, sponsored.
- Best Dressed Group: A Blue's Bakery PIE PARTY — five pies! — for your whole crew. Squad goals: achieved.
Pro tip: coordinate with your group. Five pies is a very good reason to show up in matching fascinators.
🏇 Pick Your Pony — Big Prizes Up for Grabs
Think you've got the eye of a seasoned handicapper? Put your racing instincts to the test. Everyone who correctly picks the Win, Place, AND Show horses gets entered into a raffle for these jaw-dropping prizes:
🥇 Win (1st Place Horse): A 4-Course Whiskey Dinner for four at Maxie's — a $560 value. We're talking serious Southern indulgence with hand-selected whiskey pairings. This one's a bucket-list meal.
🥈 Place (2nd Place Horse): A Maxie's Catered Delivery — a $500 value. Bring the party home. Ribs, sides, and all the good stuff delivered right to your door.
🥉 Show (3rd Place Horse): A 4-Course Wine Dinner for four at BKC — a $440 value. An elegant evening out that starts with a lucky pick.
🎟️ Even More Ways to Win
As if the prizes above weren't enough — we've also got a 50/50 raffle, a silent auction, and dozens of raffle prizes generously donated by some of Milwaukee's best local businesses, including:
Transfer Pizza • Black Twig Bakery • Aggies Bakery • Float MKE • Cousin Subs • Double B's BBQ • Bunzels • Fred's Frozen Custard • Oro Oil • MKE Film Festival • Badger CrossFit • Bensons • Nourish Skin Studio • Roots Salon • Best Place • Bars & Rec • Milwaukee Public Museum • 3rd Coast • Lucky Joe's • Lac La Belle • Sanford • Egg & Flour • Five O'Clock Steak House • WAC • Bark & Scratch • Tosa Toga • Valentine Coffee • The Neighborhood Draft
That's a lot of Milwaukee love in one room — and every ticket you buy goes toward supporting a fantastic day.
📍 Maxie's Milwaukee • May 2, 2026 • Dress the part. Bet on a winner. Make memories.
Derby Day at Maxie's is one of those afternoons that turns into a full evening before you even notice. The energy is electric, the bourbon is flowing, and there's nothing quite like watching the race with a room full of people in their finest hats.
Grab your crew. Dust off your best fascinator. And start studying those racing forms — because this year, the prizes are worth showing up for.
We'll see you at the finish line. 🌹
— The Team at Maxie's
Maxie's is part of 2X James Beard Semifinalist Black Shoe Hospitality group, alongside Story Hill BKC and Blue's Egg + Bakery.