Article authored by Meghan Roth with updates by Nancy DeVault.
The 152nd annual Kentucky Derby is set to take place on Saturday, May 2, 2026. Unlike most sporting events, the Derby is jokingly known as “the most exciting two minutes in sports.” Though the race is short, the party can last all day! While you may not be able to make it all the way to Churchill Downs in Louisville to see the race, there are spots around town where you can get in on the action. So, don your oversized hats and find out where you can sip on mint juleps to cheer on your favorite racehorse. Here's a round-up of Kentucky Derby events in Orlando.
Kentucky Derby Events in Orlando for Couples
Boxi Derby Weekend
- Where: Boxi Park Lake Nona, 6877 Tavistock Lakes Blvd, Orlando
- When: April 30-May 3, 2026 | Times vary per day
- Cost: Free entry
Boxi Park in Lake Nona is known for themed events—and, yes, that includes Kentucky Derby events in Orlando. The fun kicks off with Run for the Roses, with the run club at 6:30pm. You may not be as fast as a horse but all are welcome to trot along.
Friday keeps the festive vibes going with live music, which continues into race day on Saturday. Expect music with Jaclyn Hayden Band, DJ Digital & Griffin Sinclair Band, plus a bubble party and other happenings. Cap it off with Sunday Funday with live music with Gilly & The Girl, themed crafts, drink specials and more.
Orlando Derby Soirée at Serenity Ranch
- Where: Serenity Ranch, 8001 Clarcona Ocoee Rd., Orlando
- When: May 2, 2026 | noon to 8pm
- Cost: $37.89-$525.53
STAR 94.5 presents the Orlando Derby Soiree, with special live performances by KEM and 803 Fresh. Experience the thrill of the race in style, with drinks and food available for purchase. This event is hosted by STAR 94.5’s Monica May, plus curated music by DJ Kyle LaRue.
Kentucky Derby Affair at The Bosendorfer Lounge
- Where: 325 South Orange Ave., Orlando
- When: May 2, 2026 | 2:30pm-7pm
- Cost: Free admission
This open seating event claims to be among the most luxurious Kentucky Derby events in Orlando. It’s set to include a derby hat showcase, a mint julep experience and live music with a guitarist and pianist.
Annual Kentucky Derby Party at Forward Slash Distillery & Blending House
- Where: Forward Slash Distillery & Blending House, 650 S. Capen Ave., Winter Park
- When: May 2, 2026 | 2pm-11pm
- Cost: Free entry (21+)
This viewing party is set to feature both mint and peach juleps, bourbon and food from Speakeasy Burger (from 4-8pm). Pssst, this distillery is just around the corner from Kentucky Avenue… so that's gotta be a good sign for this event, right?!
Derby Day Extravaganza Party
- Where: Acrisure UCF Football Stadium, 4422 Knights Victory Way, Orlando
- When: May 2, 2026 | 3pm-8pm
- Cost: $125
Presented by Loyal Source, this Derby Day Extravaganza party will feature unlimited food and drinks, a live auction, raffle prizes, a 50/50 raffle, a winner’s circle, music by DJ Gonzo, dancing and much more. The party is for adults 21+. FYI, this event also has an adjacent golf tournament.
Derby Day Celebration & Hobby Horse Tournament at À La Cart
- Where: 274 N. Orange Ave., Orlando
- When: May 2, 2026 | starts at 4pm
- Cost: $15 entry into bracket-style hobby horse tournament, includes a complimentary beverage
Let’s raise a glass to the team at À La Cart for making their party the most epic of all Kentucky Derby events in Orlando. FYI, a hobby horse is a toy consisting of a stick with a stuffed horse head. So, can’t you picture the hilarious shenanigans to be had at this themed event? À La Cart will also have best-dressed contests and a lineup of craft beers and food trucks.
Kentucky Derby Top Hat Party at The Ritz-Carlton Orlando, Grande Lakes
- Where: The Ritz-Carlton Orlando, Grande Lakes, 4012 Central Florida Parkway, Orlando
- When: May 2, 2026 | 4pm-7:30pm
- Cost: $75
Sample southern appetizers and a mint julep in the Lobby Lounge sunroom as you watch the most exciting horse race. Derby attire and a reservation are required for this swanky gathering. Ages: 21+
Kentucky Derby Party at The Courtesy
- Where: 1288 N. Orange Ave., Winter Park
- When: May 2, 2026 | 4:30pm-7pm
- Cost: $42
If your idea of a Derby party is more “sip and savor,” this craft cocktail bar is your starting block. Expect a lineup of whiskeys and juleps, along with snacks by Swine and Sons. The ticket includes a welcome beverage, a commemorative Derby glass and more. Plus, The Courtesy will award gift cards and bourbon bottles for best hat and best socks.
Kentucky Derby Dinner Cruise Aboard the Barbara Lee
- Where: St. John's Rivership Company, 433 North Palmetto Ave., Sanford
- When: May 2, 2026 | 4:30pm
- Cost: $59.06
Celebrate the fast-paced Derby race aboard a leisure cruise on the beautiful St. Johns River and Lake Monroe. Guests will enjoy a delicious meal, elegant river views and live streaming of the legendary Kentucky Derby races throughout the day. Every adult guest will receive one complimentary mint julep to toast the races!
Kentucky Derby Watch Party
- Where: Lamp & Shade Craft Kitchen and Cocktails, 1336 N. Mills Ave., Orlando
- When: 4:30-8:30pm
- Cost: Free admission
With multiple indoor and outdoor screens, a live DJ and a high-energy atmosphere, Lamp & Shade is brightening up Kentucky Derby events in Orlando. Dress to impress for their Best Derby Hat and Best Dapper Dan contests and enjoy specialty cocktails crafted for the occasion.
Dapper Derby Day 2026 at Caribe Royale
- Where: Stadium Club at the Caribe Royale Orlando, 8101 World Center Dr., Orlando, FL
- When: May 2, 2026 | 5-8pm
- Cost: $81+
With proceeds benefiting UCP of Central Florida, this event includes food and beverages, sport simulator contests, a spectacular raffle and a best-dressed contest for those showing off their Derby finest. Complimentary valet and self-parking are available at the resort. The Stadium Club’s full menu of food and drinks will also be available for individual purchase. The event is for guests 21+.
Derby Daze Orlando
- Where: Great Southern Box Company, 2105 North Orange Blossom Trail, Orlando
- When: May 2, 2026 | 5pm-9:30pm
- Cost: $19
The 3rd Annual Derby Daze is a fashion-forward experience intended for the movers and shakers of the Central Florida community. There are general admission options with access to a variety of food vendors in the food hall, or a grand “Run For The Roses” VIP 4-person package ($229.25), with special seating and perks.
Derby Day Social – Orlando
- Where: American Social Orlando, 7335 W. Sand Lake Rd., Orlando
- When: May 2, 2026 | 5pm-7:30pm
- Cost: Free + VIP option
This Kentucky Derby watch party will be held on American Social’s sunlit patio. American Social is partnering with Maker’s Mark to serve signature event cocktails. VIP access ($30) grants lite bites and two complimentary drinks.
Kentucky Derby & Cinco de Mayo
- Where: 8255 International Drive, Suite 120, Orlando
- When: May 2-5, 2026
Kings is celebrating back-to-back holidays with four days of themed drink specials and interactive fun. Guests will be welcomed to the ultimate Derby watch party on May 2nd, and try their luck in the “Pick Your Pony” drawing. Beginning at 4 p.m., each guest will have the opportunity to select a card representing a racehorse, and anyone holding the winning horse at the end of the main event will receive a free bowling voucher. From May 2 – 5, guests can enjoy:
- $8 Pink Pony Margarita – Patrón Silver, triple sec, watermelon juice, lime juice, agave
- $8 Mexican Candy Shot – watermelon juice, Ghost Tequila, peach schnapps
- Shotskis for four
- $25 Modelo Towers
A Derby Soiree: Wine Club Pairing Dinner
- Where: Cooper’s Hawk Winery & Restaurant – two locations
- When: Monday, May 18, 2026, at 7pm at Waterford Lakes location (529 N Alafaya Trail) & Tuesday, May 19, 2026, at 7pm at I-Drive location (8005 International Dr., Orlando)
- Cost: $79
The big race will be long over when these two events roll around, but Cooper’s Hawk plans to keep the Derby festivities going with a themed wine pairing. The night starts with Kentucky Sweet Tea, followed by multiple food courses, including a Derby Bourbon Ball Chocolate Pecan Cake.
More Kentucky Derby Events in Orlando
- Derby Day Networking Social at The Back Porch in Longwood
- Kentucky Derbi Party at JW Marriott Orlando, Grande Lakes in Orlando
- Big Cat Derby at Central Florida Animal Rescue in St. Cloud
- Kentucky Derby at The Cove Bar in Clermont
Go the Distance: Kentucky Derby Events Just Beyond Orlando
- 6th Annual DeLand Derby at Victoria Hills Golf Club (DeLand)
- Kentucky Derby Weekend at World Equestrian Center (Ocala)
- Kentucky Derby Prix Fixe Dinner at Black Prong Resort (Branson)
Must-Dos for Kentucky Derby Events in Orlando
- Dress the part: Hats, florals and seersuckers are always welcome—even at casual spots.
- Arrive early: The main race is short, but venues fill up quickly beforehand.
- Expect themed drinks: Mint juleps are the star, but some spots get creative with craft cocktails.
- Check social media: Many venues announce Derby specials or ticketed events closer to the date.
