Fast horses, tasty bourbon, stylish boutiques, even a castle are found in this one Kentucky county

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by Patti Nickell

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).

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 in1887. 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 a half 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 multimillion-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, chili 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, 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. 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 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

Nonesuch (yes, really) and Irish Acres Antiques.

Imagine a place where staid New England drawing room meets 1930s over-the-top Hollywood glamor. 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, in 1781 having ridden 40 miles 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, drank 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.”