There’s always a lot going on in and around Louisville on Derby weekend. Starting on Thursday night, the area is full of exciting events and there are plenty of ways to enhance your Derby experience. Take a look below for some of our favorite things to do during Kentucky Derby week.
2026 Kentucky Derby Travel Package Add-Ons
Kick off your weekend with a lively and fun Kentucky experience. This Thursday evening event includes transportation between downtown Louisville and Hermitage Farm, where guests will enjoy a sunset tour of the picturesque property including the stud barn. Following the tour, you’ll have the opportunity to build your own mint julep to sip as you enjoy the views. Later, a delicious farm-to-table dinner will be served featuring southern cuisine.
The Kentucky Oaks is one of the biggest races in the country, and the most lucrative for 3-year-old fillies. It has a long history dating back to 1875 and is a great way to get yourself into the Derby spirit. In addition to the great racing, it also includes the Kentucky Oaks Fashion Contest, where ladies of all ages walk the pink carpet in their finest attire. Pink is the color of the day in honor of both the Oaks’ official flower (the stargazer lily) and their charity, Horses & Hope, so make sure to think pink when choosing your outfit!
Mingle with horse racing VIPs as you enjoy an upscale social evening complete with wonderful food and drink. Savor the exquisite Kentucky flavors of nationally renowned chefs as they compete in a live cooking showdown. The regional dishes created will be paired with great wines and followed up with live music.
Experience all things bourbon as you are expertly guided through bourbon country in this full day excursion. You’ll learn about the beverage’s long history, enjoy tastings at two premier distilleries, and discover what makes bourbon such an important part of Kentucky’s culture. Lunch and transportation from downtown Louisville is included.
What better way to spend Derby weekend than by touring horse country? This full day tour allows you to experience two different thoroughbred farms, each located on acres of beautiful rolling hills in the Bluegrass region. You’ll see past and present Derby stars as your expert guide escorts you through this beautiful part of the state. Lunch and transportation from downtown Louisville is included.
Experience the two things Kentucky is best known for in this full day tour. Start the day at a local horse farm, learning about these magnificent creatures and taking in the lovely rural scenery. Following a great local lunch, you’ll head to Bourbon Country to check out a historic distillery, complete with samples of course. Lunch and transportation from downtown Louisville is included in the tour.
Louisville’s quintessential Derby Eve party, the Barnstable Brown Gala has been held on the eve of the “Run for the Roses” for decades. Each year, this black-tie gala is attended by some of the biggest names in film, television, music, fashion, and sport. This exclusive event is the place to see and be seen on Friday night.
We’ve arranged very special Churchill Downs Backside Stables access, available only to Roadtrips’ guests. This exclusive experience provides an opportunity to get up close and personal with the horses that will be running in the Kentucky Oaks and Kentucky Derby. Alongside your knowledgeable insider guide, you’ll also meet jockeys and trainers, watch the ponies workout on the track, and gain entrance to select stables. Space is limited for this rare behind-the-scenes experience.
With over three decades of experience and many happy customers, we specialize in custom and luxury travel packages that bring you closer to the iconic Kentucky Derby and Kentucky Oaks events. Please note that the terms “Kentucky Derby” and “Kentucky Oaks” are used only to properly describe certain events, and we are not officially affiliated with the Kentucky Derby, Kentucky Oaks, or Churchill Downs. For official Kentucky Derby ticket information, please visit www.kentuckyderby.com.
“Had some of the best seats in the house”
Had some of the best seats in the house for the most exciting two minutes in sports!
“The whole Derby experience was amazing.”
The hotel suite was wonderful. The whole Derby experience was amazing. We loved the tour of the horse farm and the dinner river cruise.
“Amazing time and great experience”
Just would like to thank you so much for your services and support to make everything as seamless as possible with continuous coordination and detailed updates. The family had an amazing time and great experience at the Kentucky Derby last week! Thanks again.
“Made our Derby weekend the best we could possibly have”
Kate worked tirelessly to get our 18-person group into the best places. It really made our Derby weekend the best we could possibly have.
“Everyone was wonderful to work with!”
Everyone was wonderful to work with!!! Roadtrips went out of their way to make my clients’ experience a trip of a lifetime!!