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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. 

A Kentucky Derby FAQ – What You’re Asking and Searching For Derby Season

Apr 29, 2019

Happy Derby Week!

All the planning and prepping has led up to this week – definitely the most wonderful time of year here in Louisville. Seriously, it’s my favorite week of the year and even if you don’t go to the track, there is so much fun stuff to do. No lie, there is something for everyone.

Today I’m going to tackle a post I’ve been meaning to do FOREVER and finally got around to working on. We’re talking Derby FAQs. Certainly, this isn’t everything but I’ve included questions from you all on Instagram, as well as the ones you all email/DM me plus I looked at what people are searching for when they stumble on the blog.  If you have anything you’d like me to add, drop it in the comments and I’ll do my best to track down the answer.

Hoping this will be a helpful post for this year but also for anyone planning on making a trip to Kentucky for the Derby in the future. So let’s get down to it.


Where should I go to {eat/drink/shop}? 
Starting out with this one since it’s, by far, the one I get most often. Since it was such a popular question, I dedicated two blog posts to the topic. So check these out based on where you’re staying in town.

Where to Eat, Drink and Shop + More in Louisville
Part 1: Downtown, Nulu, Butchertown and New Albany | Part 2: Clifton, Frankfort Ave, The Highlands and St. Matthews

What parties/events should I check out? 

When it comes to galas, The Barnstable Brown party is the cream of the crop. But newcomers like The Trifecta Gala (Usher is performing this year) and The Silks Bash (a new local favorite) are other amazing options.

For parties, there are some all over town. If you want to see some of my favorites, head over here. 

At the Track

From blog search – “Is the Kentucky Oaks as dressy as the Kentucky Derby?”

In a word – yes. In the last 5 – 10 years, the Oaks has morphed from Louisville’s Day at the Track to Part 1 of the Kentucky Derby. It’s just as dressy, just as much pageantry and just as many people.

There is a slight difference though and that’s the pink theme in conjunction with the Susan G. Koman Foundation. Before the Kentucky Oaks race, there is a breast cancer survivors parade filled with woman all dressed in pink. In support of them, Churchill Downs encourages everyone to incorporate some pink into their outfit. It can be as simple as a pink feather or flower in your hat or a pink tie or pocket square for guys to a full-on look with an all-pink ensemble (this two-piece set would be perfect), a pastel pink dress or fascinator.

Other than your outfit, be prepared for just as much traffic, just as many people and all the same rules when it comes to what you can and can’t bring into the track.

From the blog search – What to wear to a business event at Churchill Downs? 

My recommendation is to still have fun with your outfit while keeping corporate decorum. Something like this dress would be perfect. A dress is certainly appropriate but you could easily do a jumpsuit as well. Don’t feel like you have to wear a jacket unless it’s something you think your colleagues/clients would expect to see.

I think a simple shift dress is always a sure bet and something you can pair with fun accessories. Depending on what day of the week, you may or may not want to wear a headpiece. If you’re going Tuesday – Wednesday, I’d say to probably avoid it (but hey, if you want to wear it – WEAR IT). You’ll see a mix on Thursday, it’s about half and half. Two years ago when I went, it was 50/50 and last year I’d say it was 60/40 of hat to no hat people.

Oaks and Derby – they’re a must.

From Instagram – “If someone is dropping you off at the track on Saturday, what is the best/most realistic location?

If you don’t mind walking, your best bet is to get dropped off on a side street off Taylor Boulevard. You can get to Taylor Blvd from the Watterson Expressway (I-264). Depending on where you’re coming from, it’s either the exit before or after Southern Parkway which is where they want to direct you to go.

You’ll get much closer if you take Taylor Boulevard and then cut over on a side street. Last year, we got dropped off right at the gate to the Churchill Downs parking lot. Once there, we were able to hop a ride on a golf cart right up to the entrance.

From IG – “First timer to Oaks on Friday. Should we try to drive and park or Uber?” 

If you have a designated driver, then you can definitely try to park. Your easiest option is parking at the Cardinal Stadium lot and taking the bus over to the track. Or you can park in one of the neighborhood lots/yards (it’s mostly yards). If you go the latter route, make sure you’re not blocked in so that you can leave when you want.

If you’re planning on having some cocktails (and I highly recommend it), I would suggest getting a ride to the track. You can Uber but you will be paying huge surge rates. If you’re local and can find/bribe a friend to drop you off, that’s your best bet. If you take an Uber, make sure to put in an address/location that is NOT Churchill Downs. You will not be allowed to be dropped off at the track, instead they’ll direct you to Cardinal Stadium where you’ll have to ride the bus. To avoid that, pick a cross street off Taylor Boulevard where you can get dropped off and walk in.

Getting there isn’t bad but getting home is the tougher part. If you can get a friend to pick you up, make sure to identify a location/time in advance. Cell service is tough with so many people there and the traffic patterns only make things worse.

My tip – watch the last one or two races AFTER the Oaks or Derby before leaving. You’ll let some people get out of the way and may have an easier time meeting up. Getting an Uber/Lyft after the race will be tough with so many people trying at once, so I’d either go with a taxi (they’re all lined up) or just be prepared to wait. You can also start trying to get one while you walk out of the track.

For any of this – PATIENCE IS KEY.

For more on parking/transportation – Churchill Downs has all the info for Oaks and Derby (that’s key – it’s different the rest of the week) here. 

From Instagram – What purse do you recommend taking? 

Per Churchill Downs, you can’t bring a bag more than 12 inches on any one side. That gives you some wiggle room on what you choose. But my #1 tip: bring a crossbody bag.

Unless you’re sitting in one of the inside dining rooms or suites, you won’t have a place for your bag to just sit. Even in the boxes, you’ll have to put it on the ground (it gets gross) so bring a crossbody bag. You’ll have a drink, your program, your betting tickets and you won’t want to mess with holding your bag. Especially in the crowded paddock and clubhouse areas.

If you go back through any of my Kentucky Derby style posts, you’ll see lots of options.

From blog search – What should I pack in my bag? 

A couple years ago I did a full post on purse essentials. Get the full run down here.

But here’s the Cliff’s Notes. Bring CASH. The ATMS often run out of money halfway through the day, so bring cash for betting and cocktails. Bring a pen that doesn’t smudge (or a permanent marker) to mark up your program and take notes before betting. Bobbie pins and a ponytail holder (for hat/hair mishaps ). Band-aids (you might need them for blisters). Mints/Gum.  And if the weather even mentions rain, pack a poncho. 

In case you didn’t know, you can also bring food into the track, as long as it’s in clear plastic bags. So it’s always a good idea to pack some snacks or sandwiches. If you’re coming in from out-of-town, just know that you can order Derby box lunches from local groceries, sandwich shops and places like Panera.

From Instagram – Should I pack flats? 

If you can, YES. If you can manage to bring in some flats or flip-flops, do it. The walk in and out of the track, especially the out part, can be killer. If you can manage to fit a pair in your bag, like these Yosi Samra foldable flats (I have a pair), do it.

From blog search – “How do you place a bet?” 

You’re in luck. I just wrote a full breakdown on how to place a bet at the track. It’s not as complicated or hard as guys in seersucker suits make it seem.

From Instagram – Where I can I get last-minute hats/fascinators? 

If you’re local (and even if you get in town on Friday), you can find a hat in SO many places. Almost every local boutique has at least a handful in stock. They also often partner with milliners so they can help you if you get in a bind.

Instagram is a great resource to find out where your local favorites will be setting up shop Derby week. Follow @headcandi, @fascinatedesigns, @finchybabyhats, @kenziekapp and @thehatgirls for a start. For more reasonable options, try Macy’s, Off Broadway Shoes or Dee’s Crafts.

Again, I can’t recommend enough stopping into local boutiques. The gals that run these spots can help you find something last minute and can often contact the milliner. Also, a lot of these local milliners have shops you can pop into. Just check out their IG for the latest.

From Instagram – “We just moved here from Louisville to Arizona – how can we watch it here?” 

The race is broadcast nationally on NBC Sports. National coverage begins at 2:30 pm and continues through the Run for the Roses at 6:50 p.m.

You can stream full coverage on NBCSports Network for the earlier races. Head over here for full coverage details. 

Use your Louisville background as a great way to meet friends and host a Derby party! You can give everyone the rundown on what Derby’s like and have an excuse to hang out and drink Mint Juleps.

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