Men’s Kentucky Derby hats: What types of hats men should wear
What type of hats are in style for the men at Churchill Downs during Kentucky Derby weekend? Let’s Talk Derby – Kathryn and Kirby have you covered.
The 2025 Kentucky Derby is just around the corner and there’s no shortage of events around town to help you celebrate. There’s something for everyone, from the Courier Journal’s Better Derby Betting event and Derby brunch, to fashion shows, cocktail classes, a children’s tea, and more.
Here are 25 events happening, in date order, between now and May 3 to help you celebrate the 2025 Kentucky Derby.
2025 Kentucky Derby-themed events in Louisville
WHAT: The 15th annual fashion show features a day full of Kentucky Derby fun with a fashion show, food, networking, sipping, silent auction, surprises, and more. Shopping, 9 a.m.; fashion show, 11:30 a.m.
WHERE: Grand Ballroom, Louisville Marriott East, 1903 Embassy Square Boulevard
WHEN: April 10, 9 a.m. to 2 p.m.
COST: $125 single (not reserved) and $1250 for a table of 10 reserved seating
MORE INFORMATION: eventbrite.com.
WHAT: Waterfront Botanical Gardens is hosting its fourth annual fashion show and luncheon featuring Kentucky Derby-season accessories for both men and women. Explore vendor pop-up shops after the event.
WHERE: Waterfront Botanical Gardens, 1435 Frankfort Ave.
WHEN: April 10, 11:30 a.m. to 1 p.m.
COST: $100
MORE INFORMATION: Proceeds to benefit Waterfront Botanical Gardens programs. waterfrontgardens.org/fascinator.
WHAT: The runway-style show presented by Dillard’s includes models showcasing men, women and children springtime apparel. Models represent more than 18 parishes in the Louisville area plus scholarship students, and Miss Kentucky, Chapel Tinius. Shannon Cogan from WAVE News is the host.
WHERE: Crown Plaza Hotel, 830 Phillips Lane
WHEN: April 10. Doors, 11 a.m.; lunch/show, noon
COST: $65, $800 patron table for 10
MORE INFORMATION: queensdaughtersinc.com/upcoming-events/2025-fashion-show-and-luncheon.
WHAT: The upscale cocktail party features signature dishes from more than 75 of Louisville’s finest restaurants and beverage companies, bourbon and wine tasting, and raffle prizes and wine and spirits pulls. Proceeds benefit the Dare to Care Food Bank.
WHERE: Louisville Slugger Field, 401 E. Main St.
WHEN: April 15, 5:30-8 p.m.
COST: $100
MORE INFORMATION: For ages 21 and older. daretocare.org/taste-of-derby-festival.
WHAT: Join stylist at J Michael’s Spa & Salon and get ready for the Kentucky Derby with hairstyle, makeup tips, skincare must-haves, mini-massages, product specials, swag bags, hors d’oeuvres from Lotsa Pasta, cocktails by Tartan House, and even some fun Derby-inspired games with prizes. Southern Spired will offer fascinators, hats, and race-inspired accessories, and Weld X Bond infinity jewelry will be selling jewelry.
WHERE: J Michael’s Spa & Salon, 4121 Shelbyville Road
WHEN: April 15, 6-9 p.m.
COST: Tickets are $35 and goes toward product purchase. Two drink tickets are included, and a cash bar is available.
MORE INFORMATION: eventbrite.com/e/annual-derby-sip-shop.
WHAT: The tea is presented by the Fillies and gives children an opportunity to enjoy a Kentucky Derby event of their own. The themed spring extravaganza features and scavenger hunt, egg coloring, face painting and a formal a formal tea party with the Kentucky Derby Festival Princesses.
WHERE: Louisville Slugger Field, 401 East Main St.
WHEN: April 19, 11 a.m. to 1 p.m.
COST: Tickets start at $35
MORE INFORMATION: Each child receives a gift bag and a keepsake photo with the Kentucky Derby Festival Princesses. Recommended for ages 3 to 8. kdf.org.
WHAT: Learn from experts how to bet on the 2025 Kentucky Derby. The Courier Journal’s lead horse racing reporter, Jason Frakes, will host the event alongside a panel of experts including Ed DeRosa of Horse Racing Nation; David Levitch, a former University of Louisville basketball player who is heavily involved in thoroughbred racing through the DC Racing ownership syndicate and as a handicapper, and Bailey Armour of 1/st Bet.
WHERE: The Sports and Social Club, 427 S. Fourth St.
WHEN: April 23, 6-8:30 p.m.
COST: $30 for general admission and $20 for subscribers, plus applicable taxes and fees. Admission includes one drink voucher.
MORE INFORMATION: usatn.enmotive.com/events/better-derby-betting-event.
WHAT: Celebrate Kentucky Derby Museum’s 40th Anniversary with an evening of cocktails, dinner, music, and the afterparty with dancing, late-night bites and a cigar bar. Rubies are optional, but white or black tie is required. Presented by Central Bank.
WHERE: Kentucky Derby Museum, 704 Central Ave.
WHEN: April 25. Red carpet, 6 p.m.; dinner 7-9 p.m.; backstretch afterparty, 9 p.m.
COST: $650 person; $150 for backstretch afterparty only
MORE INFORMATION: derbymuseum.org.
WHAT: Immerse yourself in the world of bourbon as you sample premium and rare bourbons and guided tastings. There will also be a silent auction, music, live horse racing on TV, raffles of rare and hard to find bourbons, door prizes, cigar bar and hors d’oeuvres. Presented by TKO Flight Club.
- Distilleries: Heaven Hill, Green River, Four Roses, Angels Envy, Starlight Distillery, J. Mattingly, Bardstown Bourbon, Peerless, New Riff, Jeptha Creed, Michter’s, Down Home Bourbon, Buzzards Roost, Pursuit Bourbon, Hard Truth, Bulliet Bourbon, Bluegrass Bourbon, Makers Mark, Barrel Craft Spirits, Woodford Reserve, Old Forrester, RD One, Real Truth, Neat Bourbon and Bottle Shop, Limestone Farms, Barrel Craft Spirits.
WHERE: Progress Park, 4501 Progress Boulevard
WHEN: April 26, 6-10 p.m.
COST: Tickets start at $100
MORE INFORMATION: kybourby.com.
WHAT: Enjoy opening night of Churchill Downs Spring Meet celebrating the 2025 Kentucky Derby and Kentucky Oaks post-position draws with a lavish twist with an evening inspired by “The Great Gatsby.” “The Great Gatsby” on Broadway star and Louisville native Kayla Pecchioni will be in attendance for a special performance at the iconic Pagoda. Guests are encouraged to dress in their finest 1920s attire for a Derby Week fashion contest. And Old Forester will feature a special cocktail, available at select locations, delivering a balance of sweetness and sophistication in the spirit of the 1920s.
WHERE: Churchill Downs Racetrack, 700 Central Ave.
WHEN: April 26. Gates open at 4 p.m., the first race is 5 p.m.
COST: Admission starts at $27
MORE INFORMATION: kentuckyderby.com.
WHAT: Come dressed in your Kentucky Derby attire for this afternoon tea at the legendary Seelbach Hotel and enjoy tea sandwiches, savory bites, sweets, and a specially crafted “trifecta” of hot and cold teas. Proceeds to benefit Louisville Recovery Community Connection.
WHERE: Grand Ballroom, Seelbach Hotel, 500 S. Fourth St.
WHEN: April 27, 1-3 p.m.
COST: $125
MORE INFORMATION: Derby attire, hats, and fascinators are encouraged. Valet parking available. discover.kdf.org/kentucky-derby-afternoon-tea/
WHAT: Ladies get ready for a day of golf and to support Ovarian Awareness of Kentucky. This is a two-person golf scramble.
WHERE: Polo Fields Golf & Country Club, 17001 Polo Fields Lane
WHEN: April 27, 11:30 a.m. to 6 p.m. Noon check-in, shot gun start at 1 p.m.
COST: $75 per person and includes cart rental, 18 holes of golf, tee gift, lunch, appetizers after the round
MORE INFORMATION: Proceeds to benefit Ovarian Awareness of Kentucky. eventbrite.com.
WHAT: Come out and enjoy brunch featuring a festive Kentucky breakfast, live music and tours of the Farnsley-Moremen property. Honorary host Mayor Craig Greenberg. Mistress of Ceremonies Dawn Gee. Presented by LG&E – KU and Mary & Elizabeth Hospital.
WHERE: Riverside, The Farnsley-Moremen Landing, 7410 Moorman Road
WHEN: April 27, 11 a.m. to 1:30 p.m.
COST: $125 for individuals or $950 for a table of eight.
MORE INFORMATION: Reservations are needed by April 22. 502-935-6809 or riverside-landing.org/event-calendar/
WHAT: Celebrate the start of Kentucky Derby week at the Icehouse with live music by DJ YK, DJ Cam and DJ Doro.
WHEN: April 27, 5-10 p.m.
WHERE: The Icehouse, 226 E. Washington St.
COST: Tickets start at $35
MORE INFORMATION: goodtimersentertainment.com.
WHAT: Grab your friends for an afternoon of painting, sipping, and celebrating the Kentucky Derby. No painting experience necessary, instructors will guide you every step of the way. Put on your best derby hat and get ready to unleash your inner artist.
WHERE: Total Wine & More, 4320 Summit Plaza Drive, #5
WHEN: April 28, 6-8 p.m.
COST: $45
MORE INFORMATION: eventbrite.com.
WHAT: Indulge in a wide range of culinary delights from 14 chefs each representing a stop on the Road to the Kentucky Derby at the Taste of Derby Party. The party also features live music and entertainment.
WHEN: May 1, 7 p.m.
WHERE: Kentucky International Convention Center, 221 S. 4th St.
COST: $425
MORE INFORMATION: derbyexperiences.com/kentucky-derby-2025/taste-of-derby.
WHAT: Enjoy an exclusive culinary event at historic Hermitage Farm that includes a three-course meal, a sunset tour of the horse farm and stop by the build-your-own mint julep bar.
WHERE: Hermitage Farm, 10500 US-42, Goshen
WHEN: May 1, 5-9:30 p.m.
COST: $585
MORE INFORMATION: kybourbontrail.com.
WHAT: Come dressed to impress in your best Kentucky Derby attire and enjoy cocktails at one of five premium bars, food and dancing in four areas, including an exclusive 2nd floor VIP Loft.
WHERE: Louisville Slugger Field, 401 East Main St.
WHEN: May 1, 10 p.m. to 2 a.m.
COST: $75-$130
MORE INFORMATION: eventbrite.com.
WHAT: A Derby Eve night of celebration at Angels Envy Bourbon Club (inside Cardinal Stadium). Music by DJ Bandcamp and DJ Doro.
WHEN: Friday, May 2, 10 p.m. to 3 a.m.
WHERE: 2800 S. Floyd St.
COST: Tickets start at $40
MORE INFORMATION: No ball caps, athletic wear, jeans or shorts. goodtimersentertainment.com
WHAT: Enjoy celebrity treatment as you walk down the purple carpet, open bar, signature silks smash cocktail, live music, VIP lounge, food and more. Proceeds to benefit Operation Open Arms.
WHERE: Pavilion, Locust Grove, 561 Blankenbaker Lane
WHEN: May 2, 7:30 p.m. to 12:30 a.m.
COST: $200 general admission; $250 VIP
MORE INFORMATION: silksbash.com.
WHAT: Nestled in the heart of Old Louisville, the Conrad-Caldwell House Museum provides the perfect backdrop. Festivities kick off at 10 a.m. with a Southern-inspired brunch paired with craft cocktails, carefully crafted to highlight the spirit of Oak’s Day, live music, food and live coverage of the races.
WHERE: The Conrad-Caldwell House Museum, 1402 St. James Court
WHEN: May 2, 10 a.m. to 1 p.m.
COST: $125 for individual, $500 for a table of four, $750 for a table of six
MORE INFORMATION: conradcaldwell.org/oaks-day-brunch.
WHAT: Spend Kentucky Derby Day in the heart of Paristown. Watch all the races and Kentucky Derby action live from Churchill Downs on a large outdoor screen, taste of local cuisine, sip on signature Derby cocktails, live bluegrass music in between races and take part in family friendly games, face painting and a DJ. Presented by Woodford Reserve.
WHERE: Paristown, 731 Brent St.
WHEN: May 3, noon to 8 p.m.
COST: General admission, $25, $10 for ages 11-17; free for ages 10 and under (up to two children ages 10 and under free with each ticketed adult). VIP $150 and includes a boxed lunch from The Café, two complimentary cocktails, and VIP-only access to a private bar, air-conditioned bathrooms, and The Café atrium lounge.
MORE INFORMATION: paristown.com.
WHAT: Indulge in a three-hour gourmet buffet crafted by the culinary experts at A Full Plate Catering, plus an open bar featuring Blade & Bow Bourbon, Tito’s Vodka, and more. Live music by Electria Strings and valet parking.
WHERE: Farmington Historic Home, 3033 Bardstown Road
WHEN: May 3, 10 a.m. to 1 p.m.
COST: $275 per person, table of eight, $2,000
MORE INFORMATION: historichomes.org/derbybreakfast.
WHAT: Derby Day celebration like no other, where community, entertainment, and giving back come together. Enjoy a full day of family-friendly area (open from 3 to 6 p.m.), live music, gaming, VIP experiences, and the races on screen all day. Proceeds to benefit Super Drew’s Cancer Charity and Norton Children’s Cancer Institute.
WHERE: 3rd Turn Oldham Gardens, 6300 Old La Grange Road, Crestwood
WHEN: May 3, 3-10 p.m.
COST: $15-$100
MORE INFORMATION: oldhamgardens.3rdturnbrewing.com.
WHAT: Just because the Kentucky Derby has been run doesn’t mean the party has to stop. Goodtimers throws party number three of the Derby week celebrations the Sunday after the Kentucky Derby at Old Forester’s Paristown Hall. Music by DJ Bandcamp and DJ Cam.
WHEN: May 4, 6 p.m. to 11 p.m.
WHERE: Old Forester’s Paristown Hall, 724 Brent St.
COST: Tickets start at $42
MORE INFORMATION: No ball caps. athletic wear, plain t-shirts, hoodies, sweat suits, joggers, tanks or timberlands permitted. goodtimersentertainment.com.
Reach News Clerk Gege Reed at [email protected].