Your Full Guide to Keeneland: A Perfect Day At The Races

If you’re going to Keeneland as a first-timer – remember that Keeneland is more than just betting and horses running a 1 and 1/16 mile race track! It’s an incredible piece of Southern history, with the classiest of tailgating, brightly colored dresses and sport coats, and of course – bourbon. In this post, you’ll find recommendations for what to wear to Keeneland, what to expect for a day at the races, the Keeneland meet schedule, and what to do in Lexington for a perfect weekend.

P.S. If you’re in town for the weekend, get our full guide to 50 Fun Things to Do in Lexington, Kentucky!

The History of Keeneland

Keeneland’s serene farm is nestled in the rolling green hills of Kentucky’s 2nd largest city: Lexington. Originally a non-profit racing and horse auction center, Keeneland was a horse farm owned by Jack Keene. In 1933 after the Great Depression era, Keeneland was sold to the Kentucky Association.

From 1933 to 1984, Keeneland underwent massive changes. Extending the racetrack, including enlarging the grandstand, adding a library, and building The Paddock as we know it today! Here are some pretty important dates to remember about Keeneland’s history in Kentucky:

• October 13th, 1936 – The first public meet was held!
• 1984 – Queen Elizabeth II of the United Kingdom visited Keeneland.
• 1986 – Keeneland, Kentucky was designated a United States National Landmark.

The original President of the Keeneland Association, Hal Price Headley, talked about what the mission behind Keeneland was always supposed to be, “We don’t care whether people who come here bet or not, but we want them to come out here to enjoy God’s sunshine, the fresh air, and watch horses race.”

Now home to one of the largest public libraries in the state, two months of public races, and many local events – Keeneland is a place of history and rich heritage for Kentuckians.

P.S. The reason that Keeneland is only open two months of the year for races is that Keeneland’s racetrack isn’t their primary business. They’re actually one of the biggest horse retailers in the country and have sold the most champion and stakes winner horses of any horse farm!!

P.P.S. Did you know parts of the movie ‘Seabiscuit’ were actually filmed at Keeneland? This underdog thoroughbred beat a triple crown winner in 1937!

What To Expect At Keeneland Races

First things first, expect your picture-perfect day at Keeneland to be one big wholesome party in the breezy Kentucky spring or summer.

You can rent a box, sit up in the stands, tailgate, etc. – but no matter what you’ll be a part of the lively atmosphere flowing from every horse stall and with every toss of a corn hole bean bag. (Especially if you go during the spring and fall meets!)

If you’re looking for the tailgating area – head to ‘The Hill’ earlier in the morning before the races start. People will be playing games, grilling out in some cases, and making adult beverages. You’ll notice a mix of hip hop and country music rippling through the crowds, keeping the atmosphere upbeat and fun before everyone heads in to watch the races (which start at 1:05 PM.)

The best part is seeing the cutest puppies (adorned in Southern paraphernalia) walk the grassy knoll between the parking lot and the Paddock. They’ll have Southern Tide bandanas and monogrammed leather leashes.. it’s ADORABLE!!

What You Should Bring To Tailgate

If you’ve never tailgated, there are a few things you need to know:

• Tents: A lot of people bring portable tents to set up snack tables, place the coolers away from the sun, and have a place to sit in the shade. It can get pretty warm when you’re having a good time!
• Drinks: Make sure you pack water along with your adult beverages! The last thing you want is to be dehydrated before trying to enjoy the races. (You won’t make it very far sunburnt and sun poisoned!)
• Plastic Cutlery and Cups : (Reusable if possible!) Hauling around the glass is not a good idea! (insulated cups are also best for when you’re walking around with your road-dog!) Beers cant be in glass bottles out in the open. Not sure how much that rule is enforced but it’s just the best policy not to risk shattering a glass bottle anyways!
• Sunscreen: Even if you’re at a fall race – you can still leave sunburnt!
• Tailgating Games: If you haven’t yet experienced cornhole or beer pong, this is your chance. (You can actually rent cornhole boards to bring with you just FYI!)
• Portable Speaker: You’ll want to have a little music going and leaving your car on isn’t a great idea all day.

***For the ladies: Remember to wear flats or wedges if you’re planning on tailgating! There is nothing fun about wobbling like a baby giraffe because you wore heels to walk in the grass.

Other Pre-Race Activities

Beyond playing cornhole and enjoying the crisp April or October sunshine, there is a lot to see at Keeneland. Take a walk to see the horses as they’re mounted by their riders in the Paddock. These prestigious jockeys will be sporting brightly colored jockey silks that match the coloring of the horse’s home farms, and it’s a major favorite for most kids and adults!

You may also see one of our very own Kentucky artists, Kayla Weber Nord, painting an abstract piece in the Paddock!

Keeeland eats

When you’re doe tailgating, pack up and head inside the gates to grab a snack. A few Southern delicacies will be on rotation so make sure you try a few of our Kentucky specials:

• Keeneland Breeze – The signature drink of Keeneland! A smooth cocktail of bourbon, a splash of orange liqueur, and ginger ale. This spicy cinnamon concoction has the power to cool you down on a warm day and warm your bones a little on cool days. (That’s the power of bourbon!)
• Burgoo – A mouth-watering meaty vegetable cup of soup sure to warm your bones at the fall meets!
• Soft Serve Ice Cream – perfect for those hotter late-April meets.
• Bread Pudding – Topped with Maker’s Mark bourbon sauce, Keeneland’s take on this traditional Southern dessert is delicious!

Parking at Keeneland

If you’re driving yourself to Keeneland, there are two options for parking.

• Paid Parking – by the entrance and fees vary by the time of year.
• Free Parking – In the grassy areas and requiring a short walk to the entrance gates and to the tailgating area. Buses can take you out but then you’ll have to wait. (Pack flip-flops if you’re worried about walking in heels!)

Download the Keeneland Parking Map to your phone before you go!

How To Watch The Races at Keeneland

There are a few different options for how to enjoy your time actually watching the races.

To enjoy horse racing in Kentucky – you don’t need specific seats, or a fancy box (although there are certainly options for that!) You can buy the $5 general admission tickets and have just as much fun!

It really depends on your intentions for the day and Keeneland horse racing is no different. The Keeneland race track offers a few different ways to enjoy the races:

***Know your race times! If you’re looking to watch a specific race – make sure you grab your ticket early and head inside to grab one of the race day pamphlets. Races start at 1:05 p.m. and are staggered 30 minutes apart, giving you ample opportunity to find your horses!

• General Admission: $5
  No seat but access to benches and freedom to walk around the Mezzanine Bar and watch the races from the lawn. These tickets are usually bought by the younger crowd looking to socialize – but anyone can purchase them and enjoy a great day at the races.
• Grandstand Seats: Usually $10
  Beyond the typical general admission is the next level up: ‘Grandstand Seats.’ These are typically the tickets we buy to sit down and enjoy the races from the comfort of a seat. It’s easier to handle when you’re in your 30’s and beyond, in our opinion!
• Box Seats: The box seats at Keeneland are typically handed down by families or owned by corporations making these seats harder to come by.
• Clubhouse Level: Members only access, but access to private bars and private track viewing areas makes it worthwhile.

College Day

Students from the University of Kentucky and Transylvania University get in for free making these days incredibly popular. If you’re looking for a more relaxing day to head to the spring or fall meets – these are probably not your best bets. However – if you’re looking for that fun party atmosphere – these are usually the most fun days!

We don’t gamble but if you’re wanting to try your hand, Keeneland has a full guide you can view here.

P.S. If you don’t gamble – don’t worry – there is plenty of fun to be had with your money safely in your pocket!

What To Wear To Keeneland

After you’ve decided what weekend you’re going and invited your friends to hang out at tailgate – the next step is picking your outfit.

If you’re the people-watching type – Keeneland will be a perfect day for you. Whether it’s Keeneland’s spring or fall meet, it’s the kind of event people go to see and be seen.

When considering what to wear to Keeneland, whether you’re a guy or a gal – remember that this is not Derby or Oaks at Churchill Downs. Think of your day at Keeneland as a garden party where playing corn-hole is encouraged and sunglasses are absolutely necessary!

• Dress Code: There isn’t a dress code for regular racetrack patrons – but you’ll want to dress up a bit so that you don’t stand out as too underdressed. Please remember though: This isn’t motocross. No bellies hanging out or dresses that barely cover your bum, please!!
• Keeneland Club Members: Race-goers respect the tradition of Keeneland by wearing ‘appropriate attire’ like slacks, modest dresses, etc. Anyone not deemed dressed appropriately (slacks, sport coats, dresses, pantsuits, etc) will not be permitted entry.

Trust us when we say – even when dressing more modestly – the meets aren’t a stuffy atmosphere. You’ll have fun dressed up for a couple of hours and snapping some memorable photos with your friends!!

(Photos from Keeneland Facebook)

For The Ladies

Planning ahead for what to wear for the Keeneland spring meet? I (Shelbs) typically go for the dresses and low heel sandals vibe. It’s comfortable, breezy, and looks great in all of your photos!

If you’re asking what to wear to Keeneland in the fall – think dresses, boots, tights, and all manner of cozy scarves. It’s October in Kentucky – so temperatures hover in the forties and fifties. It also tends to be a little damp this time of year, so make sure you’re properly bundled up! NO JEANS.

• Sunglasses/ Sunglasses Strap – (Sunglasses straps are the best thing when you don’t want to clutter up the tiny bag you’re allowed in!)
• Flip Flops (In April, if you wear heels, you’ll want them!)
• Dresses / Flowy skirts and off-the-shoulder tops — whatever you’ll be the most comfortable in is always the best policy. Lots of walking, and since it’s an all-day event – you’re definitely not going to want anything too tight or restrictive.
• Lip Balm (SPF!!!) – Lipstick is good – but since you’ll be drinking (even if it’s just water!) and your lipstick is bound to rub off – SPF chapstick is always a good idea.
• Sunhats – The best decision when I went a few years ago. It’s so much nicer to watch the races with a hat if you’re a photog who doesn’t like sunglasses all the time. (Keep in mind you don’t need a big Derby hat! Just a casual summer hat will do!)

Bag Policy

Backpacks and such are not permitted – so remember to grab a smaller clutch, camera bag, or diaper bag!

Every bag will be subject to inspection – consequently, try to pack the fewest things you can.

*****If you want to bring a camera – I highly suggest a camera clip on your bag! (See our current favorites either to the right on a desktop or scroll to the bottom if you’re on your phone.)

(Photos from Keeneland Facebook)

For The Men

For the guys – if you’re deciding whether or not to wear a tie or bowtie, just make sure it’s something bright and pastel in the spring!

In the fall – the more traditional navy/black sport coats are encouraged. NO JEANS.

• Sport Coats/slacks are always acceptable
• Comfortable Loafers ( No tennis shoes or leather flops.)
• Ties or bowties encouraged
• Button-down shirts and nice polos on the hot days are fine (as long as you wear nice slacks and nice shoes with a belt!)
• Belts – Speaking of belts, nice leather belts or embroidered southern-style belts like the ones above are always nice! If your pants have belt loops – throw on a belt.
• Sunglasses/ Sunglasses Strap (So they don’t fall out of your pocket and get trampled!)
• Sunscreen
• If you’re going to wear a hat – just make sure it’s not a trucker hat! Plenty of guys wear hats to Keeneland with their sport coats!

What To See At Keeneland In The Off-Season

Even though the races only run in April and October – Keeneland is still a gorgeous place to get to know Kentucky in off-season months.

• Painting At The Paddock – With Kentucky’s very own artist, Kayla Weber Nord, try your hand at a painting class! With a glass of sangria (or two) by evening light in the Paddock, you’ll create your own one-of-a-kind abstract piece of art.
  Tickets include Hors d’ oeuvres, sangria, and a 9×12 canvas.
• Take A Guided Tour – As a National Historic Landmark, it’s a perfect pit stop on your road trip across Kentucky.
• Thursday Night Live at Keeneland – Although not held every week at Keeneland, Central Bank in Lexington sponsors a live music event featuring local musicians to kick off the Spring meet. When it’s not being held at Keeneland, it’s still a great way to kick off your weekend before heading to the track on Saturday.
• Breeder’s Cup at Keeneland – After the fall meet, Keeneland sometimes launches into preparing for one of its most prestigious events – the Breeders Cup. This international event isn’t hosted at Keeneland every year, but it did start in Kentucky! 2022 will mark the third time the World Championship Breeder’s Cup has been held at Keeneland.
  Tickets Available Here

Railbird Festival

Railbird Festival is a 2-day country, bluegrass, R&B soul music extravaganza on the Keeneland grounds. In years past, Railbird Festival has hosted incredible local artists from Kentucky including our very own Tyler Childers! Beyond country and blues, artists from other genres like Hozier have also headlined. What we love about this festival is that all of the music is meant to be incredibly ‘chill‘.

The vibe that rippling through the crowd is something akin to a hillbilly hippie hoedown and we’re not mad about it!

• Tickets for Railbird can be purchased as one general admission ticket for 2 days, 2 Day VIP tickets, 1 Day General Admission, and 1 Day VIP tickets, with the option to add parking passes.

Make sure to book your hotels early! Lexington is a big city, but you’ll quickly run out of good options by not booking in advance.

The lineup for 2021 is looking even more incredible with My Morning Jacket and Leon Bridges performing on Saturday, and Dave Matthews Band, Jason Isbell, and the 400 Unit playing on Sunday. Click here for the current lineup.

Other activities at the festival include the Rickhouse bourbon tastings, Sip & Savor (gourmet small plates from world-renowned chefs), along with the Fillies and Colts kids petting zoo. If you’re considering VIP Tickets, you get access to all of these activities as well as a few more perks:

• Up-front viewing on the main stages
• VIP-only air-conditioned lounge
• VIP tent area with all-day complimentary hors d’oeuvres, water, and spa services including massages, flower crowns, and hairstyling stations by Drybar!
• Reserved parking, and a VIP gift bag!

Where To Eat In Lexington

If you’re interested in having a meal at Keeneland, check out their special events calendar here.

• Sunrise Trackside – Saturday Breakfast at Keeneland: is served during Saturdays in April at their Sunrise Trackside events. This free event is from 7 AM-8:30 AM where visitors can enjoy breakfast while watching horses go through their morning exercises on the track! After breakfast, there are opportunities for children’s activities and guided walking tours starting from the Paddock! (No reservations required!)

Restaurants Close To Keeneland

If you’re looking for great restaurants near the Keeneland Race Track, this list is for upscale restaurants down to the more casual options!

• Carson’s Food & Drink – An upscale speakeasy vibe and local favorite – serving gourmet pub food (with options for family-style dinners!)
  Address: 362 E Main St, Lexington, KY 40507
• Corto Lima – Downtown Lexington’s Latin-inspired favorite – include the Best Margarita In Lexington by Readers Choice awards in 2019!
  Address: 101 W Short St, Lexington, KY 40507
• Tony’s of Lexington – An amazing upscale steakhouse in the heart of Lexington.
  Address: 401 W Main St, Lexington, KY 40507
• Tortilleria y Taqueria Ramirez – This place is not fancy but they have over 4.5 stars on google for their awesome tacos!
  Address: 1429 Alexandria Dr, Lexington, KY 40504
• A Cup of Commonwealth – Coffee for when you’ve taken a nap and need to rally.
  Address: 105 Eastern Ave, Lexington, KY 40508
• West Main Craft & Co – An awesome cocktail bar.
  Address: 135 West Main Street, Lexington, KY 40507
• Kentucky Native Cafe – A great garden/outdoor patio to enjoy the weather.
  Address: 417 E Maxwell St unit b, Lexington, KY 40508
• Bru Burger Bar – Easy burgers, chicken fingers, and American-style food. The whole family will love it.
  Address: 3010 Lakecrest Cir, Lexington, KY 40513

Make Sure You Plan Your Rides!

Keenland is only a few minutes from downtown Lexington. That short distance may seem tempting to drive yourself to and from the track – but DON’T! (Unless you have a designated driver for tailgating!) You’ll enjoy your day much more if you don’t have to worry about driving – especially with Lexington traffic that’s only made worse on Keeneland weekends.

What Else To Do in Lexington

If you’re going to be spending a whole weekend in Lexington – beyond just your trip to Keeneland there are a few things you might want to see!

• Woodford Distillery – not the oldest distillery in Kentucky but surely one of the most prestigious! Woodford Reserve’s copper still room has been in many magazines across the South as well as their picturesque grounds. Schedule a one and a half hour tour complete with a bourbon tasting, or stop by the tasting room to round out your Kentucky experience!!
• Kentucky Horse Park – if you haven’t gotten enough of horses, you can visit the Kentucky Horse Park for a great day of interactive activities. There are four separate Museums dedicated to equine history and arts, live shows with different breeds of horses, children’s activities, and a full state-of-the-art campground!
• The Summit at Fritz Farm – If you’ve forgotten any of your carefully planned out Keeneland outfit, or you’re looking for a quick bite to eat, head to the Summit at Fritz Farm! This stunning outdoor shopping center is anything but cookie-cutter with gourmet restaurants, local clothing retailers, and wine bars!

For more Kentucky travel guides to round out your trip – check out these posts:

• 12 Perfect Kentucky Hikes This Summer
• Kentucky Spring Bucket List
• 100+ Louisville, KY Murals City Guide
• 12 Prettiest Day Trips From Louisville

Where To Stay In Lexington

Due to Keeneland only holding races in April and October – they’re incredibly popular events for Kentuckians. You can expect hotels, Airbnb’s, and really any rentals to start getting sold out pretty quickly. Use the Booking.Com widget below to find available hotels for your weekend, and stay in some of our Lexington favorites!

You’ll want to book your hotels at least a month or two in advance!

• The Kentucky Castle
• Origin Hotel
• The Sire Hotel
• A Storybrook Inn

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How To Plan The Perfect Day At Keeneland

After all your planning is complete, from finding your hotel and the perfect outfit – make sure you plan to actually enjoy your weekend getaway to Lexington. No itchy clothes, uncomfortable heels, or sunburns here! You’ll want to map out somewhere for dinner and then an easy way to get back to your hotel!

If we were planning our perfect day at Keeneland, here’s how it would go!

• Start with coffee at a local coffee house, like A Cup of Commonwealth (see best restaurants in Lexington above!)
• Then we would head to the tailgating area on The Hill around 9 AM and start prepping the tent, tables, and chairs for tailgating.
• Mimosas would start promptly at 10 AM.
• Drinks and snacks flowing continuously until around 1, when the crowd starts to flow into the Keeneland Paddock.
• After packing up the tent and tailgating supplies back into the truck, we’d grab our grandstand seats for $10 apiece, grab a Woodford and Sprite- and settle in to enjoy the races.
• When the races are over, we would work on grabbing dinner somewhere delicious and local and then finding somewhere to listen to live music!
• Following up a great day by promptly crashing into bed at 9 PM because that’s a super long day for the almost 30 and above crowd!!!

Shoot us any questions in the comments below! We’re happy to recommend hotels, restaurants, and more!

P.S. Always find the cute dogs to pet during tailgate.. 10/10 good boy pets will make your day better!

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Until next time friends,

Thanks for sharing!