What to Pack, Wear and Plan for the Perfect Fall Day at Keeneland

You guys, Keeneland opens on Friday and it’s like Mother Nature knew it. Obviously, she’s as big a fan of the Fall Meet at Keeneland as we are and is going to grace us with a high temperature of 76 degrees. Praise be!

I can promise you it was way hotter than 76 degrees when I took these photos but you gotta do what you gotta do and I’m all about getting everyone ready for one of the best traditions in the bluegrass.

Last week, I got the chance to do a behind the scenes tour of the track with Horse Country thanks to the awesome team at America’s Best Racing (more on that to come, including photos of me looking very uncomfortable riding a horse). Whether full of people or bustling with workers preparing for the meet, Keeneland is a magical place. It is so picturesque, truly what you envision when you think of horse country. I’ve said this before, but one of my favorite things about going to UK was being able to go to the track every April and October.

I wish I was heading down 64 this Friday to take in opening day but we have a wedding this weekend, so instead I’m going to share some tips I’ve picked up over the years along with some fun tidbits I learned during my behind-the-scenes tour.

When it comes to a day at Keeneland, there’s some things you’ll want to remember before you pull through the gates.

  • Take Your Outfit Up a Notch: You don’t need, nor should you, dress like you’re going to Derby but you’re going to want to up your game with your outfit. I equate it to going to a football game in the South where everyone is in dresses and button-downs when you’re used to jeans and a t-shirt.If you’re doing General Admission, this outfit is a great option. You’ll be doing a lot of standing, all those benches get claimed EARLY, so you’ll want to wear a shoe you can stand in all day. I love flat knee-high boots since they elevate your look without killing your feet. You’ll also want to be comfortable moving through crowds since it can get pretty packed in the Paddock areas on the weekends. So avoid anything fussy. You can’t go wrong with a sweater + skirt + boots combo or a printed dress + boots.If you’re going to be in the Clubhouse or one of the dining rooms, you’ll want to go a little fancier. Think the same thing you’d wear to a fall wedding. Below I’ve pulled some cute ones that still leave you with some betting money. Also, be sure to remind the guys that they will need a jacket for the Clubhouse. If you forget, they’ll make you wear one of theirs and it’s not the best look.
  • Pack the Essentials: A day at the track can be a long one.Get there early with your cooler in tow and join the rest of Central Kentucky for tailgating. Bring a full spread or just some mimosas and beers (and lots of waters… gotta stay hydrated) and enjoy the atmosphere out in the parking lot. You’ll definitely make some new friends in the process. Oh and don’t forget a couple chairs.If you’re going to grab drinks or dinner after the track, make sure to pack accordingly since a day at the track can wear you down. Pack extra hair ties or a headband, band-aids and if you wear heels, throw a pair of flats in the car to change into afterwards. And if you need some suggestions on places to try in Lexington, America’s Best Racing has an awesome list with options at every price point here.Β 
  • Bring Cash: This one may go without saying but I always forget, so I’m reminding you too. The ATM lines at the track can be long so make sure to swing by one on your way to the track so you can avoid at least one line while you’re there.

Old Navy Funnel Neck Sweater (only $20 – comes in a handful of colors)
Corduroy Skirt (more options below, love this color too)
Knee High Boots | Ray-Ban Sunglasses
Earrings from Work the Metal – Similar Here

You’ve made it to the track and are dressed to kill, now what?

  • Grab a Bite at the Track Kitchen: Okay, so this is something I just learned about on my tour. Keeneland has a track kitchen that is a little slice of history. It’s easily accessible from the parking lots and is outside of the main gates. If you’re looking to change up your experience, get there early and have breakfast there. You may end up sitting next to a jockey, trainer or owner with a horse racing later in the day.The entire space is covered in photos throughout the years and there’s a great nostalgic vibe. No need to be initiated either, the atmosphere is super welcoming and the staff is very friendly.If you don’t make it in the morning, you can swing by on your way out for a cup of Burgoo or a BBQ sandwich.
  • Try the Burgoo: Since we’re talking about the food at Keeneland, a fall day there is not complete without a cup of Burgoo. If you’re not familiar, Burgoo is a Kentucky stew that is both similar to and totally different than chilli. Just try a cup.You can get the full run-down on Burgoo and find more about Keeneland’s must-eats over here.Β 
  • Place a Bet: If you go to to Keeneland and don’t place a bet, were you even there?Don’t be intimidated by betting. It’s not as complicated as it seems. Keeneland even has Betologists who will help you nail down your bet. If you want to brush up before you go, this post will give you all my tips for betting like a pro.Also, the betting windows at Keeneland are some of the prettiest around, so if you can grab a photo there, even better, just don’t hold up the line.
  • Take a Photo: Just like you have to place a bet, you have to take a photo. Since we’re all doing it for the ‘gram, here’s some of my favorite spots at the track:* By the clock. As you can see, it’s one of Keeneland’s iconic spots. Just get there early if you don’t want it to be crowded with people and potential photo bombers.* On the balcony overlooking the Paddock: Head upstairs, grab a drink and then ask a nice stranger to grab a picture of you and your crew overlooking the Paddock.

    * The Fall Meet Poster: RIGHT when you walk in from the Clubhouse Gate, near the gift shop, there is a giant Fall Meet poster surrounded by greenery that is prime for photos.

    * The Clubhouse Lawn: If you have Clubhouse tickets, there’s no more ‘grammable spot than the lawn overlooking the track. Time it right and you may be able to get one of the track rider horses to make a cameo too.

Okay, that’s about all I’ve got for now but if you need more betting tips, visitor info or food recs, head over the America’s Best Racing because it has a TON of info to help you plan a day at the track. Can’t wait to see everyone’s pics from the track!

Keeneland Ready Dresses for Under $150

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