I didn’t know what to expect after touching down at Blue Grass Airport in Lexington, Kentucky, in my metallic pink cowboy boots; (yes, I brought pink and green cowboy boots for this trip, as I thought the occasion called for a bit of country glamour), as an official guest of the Department of Tourism and the Kentucky Governor, Andy Beshear, I wanted to impress; besides, it was my first time in Kentucky. The closest I’ve been to the state was Tennessee. Although I wasn’t initially familiar with the Bluegrass state, I did know of the famed Kentucky Derby, the renowned and celebrated horse race held at Churchill Downs every first Saturday in May 1875.
However, I quickly learned that Kentucky offers more than the event.
The Kentucky Department of Tourism invited select journalists, business owners, and tastemakers down to Kentucky for a curated trip to experience Derby 149, popular distilleries like Castle & Key and James B. Beam Distillery Co., as well as a horse farm, Coolmore, to educate their new guests on the beauty and history of their beloved state, while also thanking them for their economic contributions via tourism over the years. Over the three days at Lexington, Louisville, and Frankfort, Kentucky, we were able to see and taste the best that the state has to offer while also enjoying behind-the-scenes access to some of Kentucky’s most revered experiences and of course, crossing off attending the iconic Kentucky Derby off our bucket list.
Kentucky is best known for its entertainment culture, but not in the way one may think. Their culture includes horse racing, bluegrass music, and, yes, bourbon, and lots of it. However, I was pleasantly surprised by the luxurious activities, warm southern hospitality, and openness shown to me by everyone I’ve encountered, including the Kentucky State Troopers that graciously escorted our tour group to and fro each sighting. So, don’t count Kentucky out if you’re looking for a weekend getaway or an adventurous rendezvous rooted in culture and idyllic slow country living. View some of my top moments from the trip and educational tidbits I’ve learned.
Friday, May 5th:
After collecting my barrings and recovering from the four-hour plane ride, I slipped on my metallic green cowboy boots and linen dress to prepare for our private tour at Castle & Key Distillery in Frankfort, Kentucky. Once we all piled onto the tour bus, we were greeted with mimosas, wine, and bourbon to make the 30-minute bus ride to the distillery easier. I marveled at the sprawling open land, thoroughbred horses, and plush greenery, excited for the upcoming tour.
Castle & Key Distillery was constructed in 1887 and boasted grandiose European architecture. Its founder, Colonel Edmund Haynes Taylor, Jr.’s travels through Europe in 1869 inspired the design. Many of the structures draw from Scotland, England, Ireland, Greece, and Italy, demonstrated in the site’s gorgeous castle, gardens, and bodies of water throughout the property. Prohibition forced the closing of the distillery in 1920. Over the next century, the property changed owners and occupants several times, eventually falling into ruin.
After 40 years of neglect, the distillery was unrecognizable and required restoration. However, in 2014, Castle & Key began working with restorationists to recreate the initial look. The Old Taylor Castle has been standing proud over this site since 1887, and it first served as a distillery as early as 1819. We privately toured the castle to take in the sights, sounds and smells of Castle & Key’s spirits production, which includes bourbon, vodka, and gin. We learned that their spirits are made with the help of natural spring water. Colonel Taylor specifically selected the site where Castle & Key stands today for the quality of the springs on location. After our tour, we enjoyed lunch and a delicious tasting of their Scared Spring Vodka, Rise Spring Gin, and Castle & Key Bourbon at one of their beautifully crafted wooden and brick event spaces.
At Castle & Key, I also learned the correct or Kentuckian way of tasting bourbon: swirl your bourbon three to four times, sniff, and gently kiss the spirit before you go in for a second taste. I trust the experts, as 90% of the spirit is made in Kentucky; they know what they’re talking about.
Next, we ushered ourselves in the tour bus to travel to Versailles, Kentucky, to Coolmore stud-horse farm, about 40 minutes away from Castle & Key distillery. We were all incredibly excited to visit Coolmore, as we learned on the bus that the farm housed several Triple Crown winners (Triple Crown of Thoroughbred Racing, commonly known as the Triple Crown, is a series of horse races for three-year-old Thoroughbreds, consisting of the Kentucky Derby, Preakness Stakes, and Belmont Stakes.) The thoroughbred winners at Coolmore are horses American Pharoah and Justify. While Col. Edmund H. Taylor Jr. originally owned the land and the farm in the early 1800s, later, Dr. Bill Lockridge transformed the farm into a state-of-the-art stud fit for the finest stallions in the world. Coolmore is known worldwide for producing award-winning horses for The Kentucky Derby and beyond. On our tour of the grounds, we visited the barns and took pictures of the horses. While I was afraid to get near the horses, they were generally friendly.
After the tour, we dressed in our finest gala attire and gathered for the Derby Eve Celebration at the Old Governor’s Mansion in Frankfort, Kentucky. At the event, there was a swirl of champagne and mint juleps, a mixer in the garden, complete with a horse statue made from grass and roses, and of course, a bourbon bar where you could sample spirits from top bourbon and whisky companies. With delicious fare from prosciutto, lamb chops, and cheese, I also tried a Kentuckian delicacy, Burgoo (A stew similar to Irish or Mulligan stew, often served with cornbread or corn muffins.) In addition to the Kentucky Governor, other governors were in attendance, like the very handsome Wes Moore, Governor of Maryland.
Saturday, May 6th:
Derby Day! After slowly recovering from the festivities, we had to wake up very early to dress in our Derby best. Luckily for me, a featured milliner of Kentucky Derby 149, The Hat Girls, provided a Derby-approved hat. The style was eerily reminiscent of one of our favorite Real Housewives of Atlanta housewives, Phaedra Parks. My gorgeously constructed hat touted a wide white brim and feathers. When asked about the inspiration behind the hats and how they create each style, Rachel Bell, creator of the brand, responded, “We get inspiration from all walks of life – whether it’s a custom-designed couch we saw on Instagram, flowers growing in the garden – just about anything can spark an idea within us and then we use that to create a new hat design,” she says to ESSENCE. She also explained that hats had been integral to the Kentucky Derby since its inception and are a big part of the entire week at Churchill Downs. The hats are a great form of self-expression and have helped create a niche industry that complements the long-standing tradition of the Derby.
After putting my bells and whistles on, I was whisked off to Keene Place for a traditional southern breakfast with deviled eggs, hash, shrimp, grits, and prosecco. Keene Place Mansion in Lexington, Kentucky, is just what you would imagine an old southern home built in the early 1800s to be, grand, distinctive, and traditionally American. At Keene Place, we were also greeted by a betologist, a specialized expert whose primary responsibility is to help people make bets for Derby and other horse races and learn more about handicapping. He gave us some valuable tips to help us prepare for Derby, bet on horses with lower odds, bet a low amount the first time, and you can bet on a horse to win, place, or show. I was not so lucky in the betting department at Derby (more on that later).
Next, we headed to Churchill Downs in Louisville, Kentucky, to attend the 149th Kentucky Derby. I was thankful it didn’t rain, as legend says horses bring the rain the first weekend of each May. We settled at the lush First Turn Club, situated on the iconic first turn of the racetrack. The exclusive section offered a front-row seat to thunderous racing and the famous Kentucky Derby Walkover. Contenders and their connections parade along the track from the barn area to the Paddock before the big race. The dining interior reserved only for First Turn guests boasts a wrap-around video board, state of the art seating experience of 5,000 square feet, and high-definition televisions throughout the space. The dining area also has trackside access to a reserved viewing terrace of the race, beautiful Twin Spires, and the majestic nature of Churchill Downs. Once acquainted with the space, it was time to bet! Unfortunately, I lost my first-ever bet but quickly learned to accept it and move on. A few mint juleps and Vodka Lilys later, it was time for the big race. With a sea of hats and fascinators, we eagerly watched Maje #8, the 15-1 long shot, take first place. Our group clinked glasses to celebrate the epic win, and l lit a cigar.
Two main Derby takeaways, wear comfortable shoes and always bring cash to bet.
We thought we escaped the rain, as it was a miraculously dry and sunny day from 11 am-7 pm, but it started to downpour after we got back on the bus. We were heading to our last stop on the trip, the James B. Beam Distillery in Clermont, Kentucky, for a private tour and kitchen table dinner. Exhausted from Derby festivities, we managed to muster up some energy to make a custom bourbon bottle and then enjoy a delicious dinner.
We sleepily arrived at our hotel at midnight and prepared to leave the Bluegrass State in the morning. After not knowing what to expect on my first trip to Kentucky, I was pleasantly surprised and satisfied and won’t hesitate to return.