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Field Guide: Lexington, Kentucky

Bourbon and horse racing are a winning combination for this charming college town in the heart of the Bluegrass State.

Written By:  Kristin Luna

Photographers:  Kristin Luna

Field Guide: Lexington, Kentucky

getting there

Lexington is 215 miles—or three and a half hours by car—northeast of Nashville.


The character-filled Gratz Park Inn (rooms from $179) charms as one of downtown’s best B&Bs and the only boutique in the historic district. For a bigger hotel, a pair of high-rises with easy access to the arena and convention center—the Hyatt Regency Lexington (from $153) and Downtown Hilton Lexington (from $139)—tower over Triangle Park.


Lexington celebrates two race months each year—in spring and fall—during which thousands of visitors take the stands at one of the country’s grandest racetracks, steeped in history and tradition. (Don’t even consider dressing down for this event; the ladies wear dresses, heels, and hats while the men don their Sunday best.) Keeneland’s annual yearling sales takes place the last two weeks of September, leading up to the fall race season, which kicks off on October 2.

And for the first time in the event’s 31-year history, the track will host the biggest fête of them all: the annual Breeders’ Cup World Championships on October 30 and 31, featuring such notable racers as this year’s Triple Crown winner, American Pharaoh. Pre-championship festivities start that Wednesday with a Jocktails charity event in which the jockeys serve as bartenders, followed by a Taste of the World dinner the next evening. Race-goers will want to be sure to check out the new premium seating (a $5 million investment), which includes the Bourbon Lounge and Luxury Chalets.

September is also National Bourbon Heritage Month, and Kentucky has no dearth of options. The closest major distillery to Lexington, Woodford Reserve, occupies some of the prettiest countryside around, surrounded by green pastures and horse farms. Tours ($10), complete with tastings, occur seven days a week, and advanced reservations are recommended. Maker’s Mark, one of the state’s biggest brands, is teaming up with Breeders’ Cup to launch an exclusive bottle collection in conjunction with the event; attendees at the Prelude to the Breeders’ Cup on October 29 can purchase the special edition Breeders’ Cup/Maker’s Mark bottles. The Maker’s distillery, located 65 miles southwest of Lexington in Loretto, is also open daily for tours ($9), during which visitors can hand-dip their own commemorative bottle to purchase and take home as a souvenir.


Azur Restaurant & Patio capitalizes on Kentucky’s finest assets with a menu of bourbon-inspired drinks paving the way for a menu of creative twists on Southern classics. Nosh on the fried green tomatoes with smoked salmon and pimento cheese or the pork belly hot wings to start. Luxuriate in bourbon fried chicken or brined pork chop and finish with an over-the-top dessert like pistachio blood orange cheesecake or an apple stack cake.

For a fine dining experience, Dudley’s on Short brings the track lifestyle to the table with a menu of upscale surf and turf and an overarching horse theme (think jockey jerseys, trophies, and other race paraphernalia). One of the newest restaurants in town, the chef-driven OBC Kitchen in the Lansdowne shopping center, pleases with flavor-packed dishes such as the bacon in a glass starter with honey bourbon, sugar glaze, and peanut butter accompaniment or a spicy buttermilk brined fried chicken that’s dressed up with candied walnuts, vanilla bourbon sorghum, hot pepper honey, and cornmeal cheddar-chive waffles.


Distilleries aside, there are plenty of places to get your bourbon fix, but three-year-old Belle’s Cocktail House is among the best of them with a swanky interior, more than 100 bourbons on rotation, and an emphasis on craft cocktails. For those who prefer beer to the heavy stuff, the city boasts a burgeoning beer scene, too, with a number of craft breweries like Country Boy Brewing, West Sixth Brewing, and Lexington Beerworks clustered around the downtown landscape.

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