Where can you taste the world’s best bourbon, make the acquaintance of the world’s most famous Thoroughbred, tour the home of the “Paul Revere of the South,” shop for high-end antiques in a converted schoolhouse, and spend the night in a castle—all in the same small county?
If you said Woodford County, Kentucky, go to the head of the class.
Located in the state’s scenic Bluegrass Region, Woodford County offers enough to keep a visitor occupied for an entire vacation.
Start with the Thoroughbreds. Drive along US 60, and you will quickly discover that you are in an upscale neighborhood where the sprawling farms belong to folks such as the Sheikh of Dubai (Gainsborough at Darley) and Barbara Jackson, widow of California wine magnate Jess Jackson (Stonestreet).
Most visitors make a beeline for Coolmore at Ashford Stud, where Triple Crown and Breeder’s Cup winner American Pharoah stands at stud.
The superstar stallion, along with his stablemate, fellow Triple Crown winner Justified, will happily pose for pictures with adoring fans. These guys preen, prance, and mug for the cameras in a manner the Kardashians might envy.
If you want a Thoroughbred farm with history, opt for Airdrie Stud, which occupies part of the fabled Woodburn Farm, considered by many to be the birthplace of the American Thoroughbred breeding industry.
Before the Civil War, it was Belle Mead Plantation outside of Nashville that was considered de rigueur for quality blooded horses. During the war, however, these valuable Thoroughbreds were routinely confiscated by both Union and Confederate forces.
Belle Meade’s owner sent his best stallions and mares to Woodburn for safekeeping, thus sowing the seeds of the Kentucky Thoroughbred industry.
Many of Woodford County’s farms are available for touring through VisitHorseCountry.com
By now, you’re ready for some Kentucky elixir, right? Take a drive through some of the United States’ most scenic countryside (Old Frankfort Pike in the county has been designated a National Scenic Byway) to arrive at Woodford Reserve Distillery.
Situated on picturesque Glenn’s Creek, Woodford Reserve is the oldest distillery in the state, with a tradition dating back to early 1800s distiller Elijah Pepper. On a tour, get a close-up look at the triple distillation process—from the copper pot still to the only surviving stone-aging warehouses in the United States. Afterward, enjoy a tasting of the official Kentucky Derby bourbon.
If you’re still in a bourbon frame of mind, head four miles down McCracken Pike, where Glenn’s Creek narrows to a trickle, and you will see a turreted castle rising above the trees. Don’t worry—you’re not hallucinating.
Welcome to Castle & Key Distillery, where the legendary E.H. Taylor Jr. began making bourbon in 1887. During his tenure, Taylor spared no expense in making what was then the Old Taylor Distillery a showplace.
Following Prohibition, the distillery fell into ruin for half a century—increasingly looking less like a Sir Walter Scott castle and more like a William Faulkner decaying Southern Gothic mansion.
That changed in 2018 when a multi-million-dollar renovation brought Castle & Key back to its original elegance. The castle, peristyle, and springhouse, with its chandelier and elegant columns, were restored. The original sunken gardens were recreated and are at their best in summer when the hydrangeas are in bloom.
Finally, in 2022, the distillery’s Small Batch Kentucky Straight Bourbon became the first bourbon produced here in nearly five decades.
Want to soak up the bourbon with some regional cuisine? The Stave, where the food is described as “sleekly sophisticated without being pretentious,” sits between the two distilleries.
In the summer, you can dine on a wooden deck among trees backing up to the creek and listen to live music.
The rest of the year, grab one of the hotly contested inside tables and indulge your taste buds with all manner of home-style cooking—from bacon jam grilled cheese and hot honey fried chicken to blackened catfish and grits and confit chicken leg served with creamy grits, roasted wild mushrooms, chile oil, and herbs.
For a completely different culinary experience, book a table at Vallozzi’s Restaurant in the county seat of Versailles (please note that in Woodford County, it’s pronounced vur-sales and not vur-sigh).
Located in the town’s spiffed-up former police station, Vallozzi’s is complete with brick walls, artwork, and cool light fixtures, along with a bar featuring an impressive array of bourbons.
The Italian menu is robust. As an antipasto, try the Arancini (fried risotto, mozzarella, and marinara), then move on to the chopped salad bursting with flavor (pepperoncini, red onion, garbanzo beans, tomato, and cucumber tossed in a well-seasoned Italian dressing), and as an entrée, try the chicken parmesan or lobster risotto.
No talk of dining in Woodford County can be complete without mentioning multi-James Beard-nominated chef Ouita Michel. Ms. Michel has amassed a restaurant empire in the Bluegrass Region, but her flagship is Holly Hill Inn, located in the charming railroad community of Midway.
Originally an early 19th-century tavern, the inn has southern charm equaled only by Ms. Michel’s inventive cuisine. She makes a cheddar crab puff to die for, and if you follow that with a boneless ribeye with Henry Bain sauce and horseradish cream and a cheeseboard composed of all local cheeses for dessert, you will have a meal not soon forgotten.
Appetite sated, it’s time for more exploring. Browse the boutiques and galleries of Midway before heading to the hamlet of Nonesuch (yes, really) and Irish Acres Antiques.
Imagine a place where staid New England drawing room meets 1930s over-the-top Hollywood glamour. You’ll find it at this rehabbed former elementary schoolhouse turned upscale antiques emporium, where you can pick up a beautifully crafted Christmas ornament for $20 or walk out with a 200-year-old mahogany cupboard for $38,500.
In what was the school cafeteria, The Glitz is a restaurant that resembles a Tinseltown movie set, with its color scheme of black, silver, mauve, and pink and its décor of smoky mirrors, gauzy drapery, and hundreds of twinkling lights.
If you’re a history buff, tour the Jack Jouett House, an unassuming Federal-style home built in 1797 for its namesake. Jack Jouett isn’t exactly a household name outside of the commonwealth of Kentucky, but here he is known as the Paul Revere of the South, as he rode 40 miles in 1781 to Monticello and Charlottesville to warn Virginia Gov. Thomas Jefferson and the General Assembly that the British were coming.
After a full day of touring and eating, anyone would be thrilled to head to a well-appointed luxury hotel for the night, especially if that hotel is The Kentucky Castle, Woodford County’s version of Downton Abbey.
Originally built by a Kentuckian with deep pockets as a home for his bride, the castle now offers a truly regal experience on a property spread across 110 acres of rolling Bluegrass countryside.
Accommodations are in the castle’s main building (where opulent features such as gilded mirrors, chandeliers, decorative molding, ceiling frescoes, and a sweeping staircase are jaw-dropping); the turrets, or cabins, on the outskirts of the estate offer a glamping experience.
Dine in the restaurant and then cap off the evening with a bourbon cocktail in the bar. Or unwind in the tranquility of the castle’s gorgeous spa, where you can opt for a Warm Himalayan Salt Stone Massage or one of their signature body scrubs, combining mint and lavender from the hotel gardens with—what else?—bourbon. If that doesn’t relax you, nothing will.
You’ve seen the horses, drunk the bourbon, toured the unique places, sampled the food, and feel you’ve checked all the boxes.
Wrong. You haven’t even started drinking wine (Woodford County has four wineries), picking fruit at Eckerd’s Orchard, or learning the lore of the rail at the Bluegrass Scenic Railroad and Museum.
Don’t worry. That just means another visit to “the most charming county you’ve never heard of.”
