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Just an overcommitted girl trying to keep up with it all. Mom of three, co-owner of Lemonade PR, sports lover and F1 enthusiast always counting down to the Kentucky Derby. 

My Favorite Kentucky Derby Season Events

Apr 10, 2019

I’ve said this before and I’ll say it again, I’m not one of those bloggers that gets a TON of questions.

“A lot of ya’ll have been asking about my ________ (skin care routine, work outs, living room furniture, car maintenance, vacuuming routine).”

Yeah that’s not me. But one thing I do get a pretty consistent stream of questions about is Derby – what to wear, where to find hats/fascinators and what to do. These are especially frequent from those of you all that have recently moved to Louisville. These are some of my favorite questions to answer and I frequently share WAY too much info when people DM me with those asks.

So today I’m sharing some of my favorite Derby season events. This is IN NO WAY a comprehensive list. There are dozens and dozens of events here in town this time of year. It’s one of the reasons it’s my FAVORITE month in Louisville. But, of course, there’s no way one person could make it to every single event so these are just some of my personal favorites. If you have something you’d like me add, just drop it in the comments or let me know on Facebook or Instagram, and I’ll add it in.

Oh and before going into my traditional favorites, here’s a quick shameless plug for an event I’m hosting this Sunday, April 14 at Off Broadway Shoes (4600 Shelbyville Rd) from 1 to 5 pm. I’ll be there helping you finish off (or start or get halfway through) your Derby look. They’ll have hats from C.K. Nobles Millinery along with their huge selection of hats and fascinators that start at $19.99 (perfect for wearing as is or embellishing at home). Everything will be 20% off and they’ll have Buy One, Get One 50% off deals as well. It should be fun and I would LOVE to see some of you all. Oh and if you head over here, there’s a little giveaway going on.

Without further ado…

Kentucky Derby Festival Events 
  • Thunder Over Louisville – Saturday, April 13

    I know this is a pretty obvious choice but you can’t talk about Derby season without mentioning Thunder. It’s the officially kick off of the season and let’s just say it starts with a BANG! Thunder Over Louisville is the largest fireworks show in North America (yup, that’s for real. take that NYC 4th of July).

    Thunder is tricky though. If you’ve never been it’s hard to know where to go. While the Great Lawn can be fun, it can also be a bit of a s**t show. Your best bet is to find somewhere to watch with ready access to restrooms as well as a little relief from the elements (blazing heat, freezing temps, pouring rain – you never know what you might get).

    My favorite spot to spend the day is the Louisville Bats stadium. Take in a baseball game, grab some ballpark snacks and beers, watch the airshow and then hang out for the big fireworks display. Limited tickets are still available here. 

    No matter where you watch, make sure you dress for the entire day. The weather can change pretty easily so you’ll want to make sure you’re ready for the long haul. It may be 85 degrees at noon and 55 degrees when the fireworks start. Plan appropriately. Also, I’d recommend closed toed shoes (lots of glass) and plenty of snacks and drinks.

  • Chow Wagon  – April 25 through May 3  

    If you love fair food, this is your spot. Think funnel cakes, super sweet lemonade, gyros, those twirly fried potatoes and so much more. Come for the food, stay for the nightly concerts. There’s live music every night so it’s a great place to go grab a couple beers with friends on a nice night. Don’t be worried about bringing the kids either, it’s family friendly.

  • Great Balloon Glow – Friday April 26 

    This is probably one of the most family-friendly Derby events. Before the Great Balloon Race comes the Balloon Glow where all of the hot air balloons racing fire their burners. It’s a beautiful night at the Kentucky Expo Center where you can wander and see the balloons glow against the blackness of the night sky, synchronized to a special musical score.

Other Notable Events: The Kentucky Derby Festival Marathon (sadly not running this year), The Great Bed Races and the WineFest. Head over here for a full list of KDF events. 

Tommy Hilfiger Scuba Front Zip Sheath Dress (Under $100) c/o Macy’s 
Black Fascinator c/o Macy’s (similar here)
Rebecca Minkoff Andree Sandals

Derby Favorites
  • Jocktails – Wednesday May 1

    Jocktails is always one of my favorite nights of Derby week. It’s definitely a locals night out, a big kick-off the extended weekend of non-stop parties that is Derby weekend. Jocktails is a charitable event to benefit the Permanently Disabled Jockey Fund (PDJF) where the jockeys, often times those riding in the Kentucky Derby, tend bar with their tips going to the charity.

    Full disclosure: one of my good friends and former colleagues Joey Wagner puts on this event so I may be biased but no matter, I mark it in my calendar as a must-attend every year. This is an invite-only event but if you follow Jocktails and JWagner Group on Instagram, they sometimes do a ticket giveaway.

  • Dawn at the Downs – Tuesday April 30 through Thursday May 2 

    There is something really magical (yes, I know that’s cheesy but it’s true) about being at Churchill Downs first thing in the morning. There’s an excitement and energy in the air that’s palpable. It’s also the best time to get up close and personal with the weekend’s biggest stars – the horses.

    Clear your schedule one morning and bring the kids or make it a morning date. You’ll see the sun rise while watching the horses run through their morning workouts. Guarantee you’ll have a Derby favorite after seeing a few race by. You can also buy tickets to enjoy breakfast while you’re there. Just so you know though, it’s not a requirement, you can just buy a General Admission ticket at the gates.

A Stitzel-Weller Affair by Blade & Bow Whiskey – Friday, May 3

We went to this Derby-eve dinner for the first time last year and it was an immediate favorite. Dreamy is probably the best word to describe the evening. The Stitzel-Weller distillery is just outside of downtown but feels like it’s in the middle of horse country. You drive in and are immediately transported.

The set-up is gorgeous, the food is delicious (Hugh Acheson did the dinner last year) and the bourbon is spot on. Oh and did I mention they had a thoroughbred horse there? Yeah that was fun.  This year the dinner will be done by Brooks Reitz and features a performance by Mt. Joy. All the details and tickets information can be found over here. 


Other Notables:
  • Rabbit Hole Distillery Esquire Lounge – April 2 – 4

    I didn’t get to go but I heard last year’s Rabbit Hole Derby party was pretty incredible. This year they are hosting the Esquire Lounge with parties and dinners each night. Looks like a good time and the location is pretty spot on in the middle of Nulu. Updated: You can save 5% on any ticket with code 5LOUWHAT

  • Bowl for the Roses – Thursday May 2 

    If you’ve lived in Louisville for a while, you may remember this event from a while back. Well this year, they’re bringing it back. If you’re a big sports fan, this is the event to go to. There’s usually an array of NBA and NFL stars in attendance, you may even see some former Kentucky Wildcats and Louisville Cardinals in attendance.

    For the big comeback, they have DJ Vice headlining the charity bowling tournament at Main Event. Should be a good time.

  • Barnstable Brown Party – Friday, April 3

    Tickets are pricey and exclusive for the main event but if you want to see famous people, go camp out to see the red carpet at the Barnstable’s Highlands home. You may get a high five from regulars like Tom Brady, Wes Welker, Joey Fatone and an array of random celebs of varying degrees of fame.

Personal Faves
  • Dinner at Jack Fry’s

    My best friend Kelly has the luck of a May 1 birthday which ALWAYS falls during Derby Week. About five or six years ago we started celebrating with a dinner at Jack Fry’s on the Tuesday or Wednesday of the week. It’s usually just the four of us but I love having a personal tradition that we return to time and time again. Unfortunately they stopped playing ‘Happy Birthday’ on the piano but the lively atmosphere coupled with delicious food is a great start to the week.

    You don’t need to go to Jack Fry’s but I highly recommend starting a tradition like this. My only tip – you’ll want to make reservations pretty far in advance. But you can still call now and have them put your name down in case of cancellations (which can easily happen with travel woes).

  • Derby Sing-A-Long

    One of our closest friends has an aunt that hosts an annual Derby morning breakfast. It’s a come one and all type of party that I started going to with Drew when we were still right out of college and going to the infield (still my favorite place). There’s beer and breakfast but the best part is a sing-a-long where she passes out song sheets and everyone gathers around her piano to belt out the most random songs – think America the Beautiful, She’ll be Coming Around the Mountain and the crowd-favorite, 12 Days of Christmas.

    It probably sounds a little different (it is) but it is one of my FAVORITE THINGS. We haven’t been in a couple years but thinking we may need to swing by again this year.

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