I grew up in a Kentucky Derby family. I have distinct memories of my grandpa giving me, my sister, and our cousins a betting pool of quarters – we picked our horses based on their names back then, statistics be darned – and I’ll never forget watching TV all day on the first Saturday in May just to gape at the Derby hats.
Now, I’ve been lucky enough to attend Derby, cementing my love for horse racing culture and fashion (of course). I also learned how to read a race program somewhere along the line, which makes placing bets just a little bit more fun.
I love a Trifecta box, in case you were chomping at the bit to know my favorite bet.
These days, to get us through until May at Churchill Downs arrives, my husband and I make an annual trip to the Keeneland Fall Meet, which never disappoints.
Keeneland is among the most stunning – if not the most stunning – horse racing tracks in the United States. As soon as you enter the grounds, it’s as if you’ve stepped into a bygone era when everything is a little more genteel – a respite, if you will, from the chaos of day-to-day life.
The track hosts both a Spring Meet and Fall Meet annually but also serves as the location of numerous stock sales. Furthermore, horses – including Triple Crown contenders – train at Keeneland year-round.
Plus, there’s a Moet and Chandon kiosk (as if you needed another reason to visit).
This year, we had the good fortune to connect with Origin Hotel Lexington ahead of our weekend trip, and I’m so glad we did.
We arrived at the hotel after a day in the always-fabulous Lexington/Kentucky Room, where we were immediately greeted by the sweetest staff members I think I’ve ever encountered – truly Southern hospitality is alive and well at Origin.
Our room boasted the perfect combination of historical touches celebrating Lexington’s horse racing and bourbon trail history – check out the vintage map on the wall – and modern amenities like a massive walk-in shower.
After a quick change upstairs, we returned to the lobby area to visit 33 Staves.
This was definitely the highlight of our evening – you can’t beat prime time college football, good drinks, a Southern gourmet food menu, and a perfectly designed bar.
We spent several hours watching games and chatting with our bartender, Andrew, who was (and I do not exaggerate) the best bartender I have EVER had. I mean, just peep this mint julep.
At one point, after discussing my love of all things Prohibition era and learning he used to work in a speakeasy-themed establishment, we asked him to surprise us with our next round. He crafted a vintage daiquiri for my husband and the most delicious whiskey Negroni I’ve ever had for me – if you’re ever in the Bluegrass, do not skip a trip to 33 Staves in the evening!
Then, make sure you return for brunch the next morning. With a full menu, including customizable omelets and amazing avocado toast, you can’t go wrong.
Overnight, the vibe of the space somehow magically shifts from a rustic-cool nightlife spot to a cheerful, sun-filled location to start the day – you really can’t go wrong.
For families: Although we visited Origin Hotel without our daughters this trip, it’s a great place for families with little ones, too! The lobby offers a large table for board games and conversation (we saw several families playing games during our stay!) and there are hobby horses for kids to use, which I thought was an absolutely adorable detail.
More About Origin Hotel Lexington
Next time you find yourself in bourbon country, don’t miss out on Origin Hotel. Conveniently located near Draper James, Pottery Barn, Williams-Sonoma, and more at The Summit at Fritz Farm, you’ll get a true taste of the Bluegrass State with a dose of upscale charm.
As the hotel’s website says:
Here, you’ll find that we take things slow—but rarely in moderation, whether it’s our Southern hospitality, record-breaking racehorses, or world-class bourbon. With a locally-inspired hotel design, Origin Lexington, a Wyndham Hotel, brings you a truly authentic Kentucky experience.
Have you ever spent a Keeneland weekend in Lexington, KY?