Bourbon, bluegrass, basketball, barbecue, and broodmares—consider these Kentucky’s five Bs. And in Lexington, with its uprising of microbreweries, “beer” completes a fine second-letter sextet. Suffice it to say, Kentucky is a state with its priorities straight.
Although Louisville, with its multitude of bridges crossing the Ohio River, looks more like Portland, Ore., Lexington is actually the Portland to Louisville’s Seattle, a small city with happy residents who probably don’t want to let the rest of the country know how good they’ve got it, for fear of carpetbagging. Yet for the amount of money that sustains the area’s lucrative Thoroughbred industry, there’s not a lot of snobbery on display. This friendly, egalitarian ethos extends to Lexington’s limestone jewel of a racetrack, Keeneland Race Course.
If you’ve ever dreamed of a horse track, Keeneland is the track you’ve dreamed of. (And if you caught “Seabiscuit,” you’ve also seen it on the big screen.) Gray-stoned and festooned with green pennants, it’s surrounded by nothing but hills and horses. Its parking area is grassy and festive, with a blue-blazered tailgate scene sharing more in common with Ole Miss’s Grove than that of any other horse track. Boasting live racing only two months out of the year—April and October—every day that hooves hit the turf at Keeneland is a special one, and the caliber of racing it cards supports such a notion.
While there is but one way — Versailles Road — to physically access Keeneland, Lexington’s FM radio dial offers a pair of appropriate sonic companions for your entrance to the track’s bucolic parking area. On Saturdays from 10 a.m. to noon, WRFL (Radio Free Lexington, operated by the University of Kentucky) features "Blue Yodel" at 88.1, where you might hear a bluegrass cover of a Dylan tune. Further down at 102.1, WKYL plays classical selections like Gershwin’s “Rhapsody in Blue.”
For a sport that appeals to both Cadillac and combine drivers, alternating between the two on your drive in is probably the best prescription.
While Keeneland has an organized extravaganza called The Hill, such structure, while welcome, isn’t necessary to get track-goers into the prerace spirit (or spirits). Whether it’s a card table set up next to a freshly waxed Ford or some youthful bourbon enthusiasts cavorting around the perimeter of a charter bus, Keeneland is as close as horse racing gets to a proper SEC tailgate scene.
In April, the Blue Grass Stakes holds distinction as a first-rate Kentucky Derby prep race, as well as a slew of top-level races like the Maker's 46 Mile and the Jenny Wiley Stakes. And in October the meet is highlighted by two Grade 1 races for 2-year-olds, the Darley Alcibiades and the Claiborne Breeders’ Futurity, as well as the mid-meet Queen Elizabeth II Challenge Cup, a top-flight turf route for 3-year-old fillies.
While there are certain rooms within the grandstand that appeal to the well-heeled, one of Keeneland’s charms is its lack of overt classism. For sustenance, a Chicago-style dog will do just fine, though the track's burgoo and bread pudding are noteworthy. The track’s signature cocktail is a Keeneland Breeze, comprised of Maker’s Mark, ginger ale, and orange liqueur.
Where to Drink and Eat
As the home to the University of Kentucky, Lexington is a semi-major Southern city that’s blessed with the cultural sensibilities of a college town — a really sweet combination, if you can find it. Nowhere is this confluence more effervescent than on Jefferson Street, which traverses a historic neighborhood on the outskirts of downtown.
Comprised of shotgun houses and columned estates, with Transylvania University as its architectural fulcrum, Jefferson and the parallel-running Limestone Street offer an eclectic, relaxed vibe on the embers of what once was a more desolate district. If you’re a dive-bar aficionado, the Green Lantern (on Jefferson) and Al’s Bar (on Limestone) are cheap, welcoming and appropriately shopworn. With Paul McCartney’s bizarre “Temporary Secretary” playing on the jukebox, the latter bar offers a signature onion and pretzel soup, a bourbon and hot cider special, and live music nightly. Bottled beer is stored in portable coolers, with a ton of shelf space devoted to dusty bourbon bottles, and precious little real estate dedicated to clearer booze. “In God we trust,” reads a sign behind the bar. “All others pay cash.”
Across the street from Al’s is North Lime Donuts, where a tasty glazed and a café au lait can stave off the sternest of hangovers. Back on Jefferson, near Short Street (one of Lexington’s more scenic roads to take a stroll on), is Stella’s Kentucky Deli, with an astonishingly diverse menu that includes a must-order Kentucky pie, a delicious chocolate chip cookie/pecan pie hybrid that’s unique to the region.
Occupying a narrower niche a few blocks down Jefferson is the trendy, rustic County Club, which focuses on smoked-meat sandwiches and serves up a tasty smoked lemonade and bourbon cocktail. Out by its bocce ball court is a large public park, which contains a rink for roller hockey, and a block away is West Sixth Brewing, where the cocoa porter is ideal on a cool night.
For a more every-bar vibe in the heart of downtown, there’s Parlay Social, where a stellar cover bands rock out on a regular basis. And for a mealtime experience more befitting of the southern archetype, ordering a plate of fried chicken (ask for all thighs) at the Merrick Inn on the other side of town won’t let you down.
If you’ve got a designated driver and a taste for brown booze, you can follow Kentucky’s Bourbon Trail to such distilleries as Maker’s Mark, Jim Beam, Bulleit, Woodford Reserve, Evan Williams, and Wild Turkey. But the smoothest Kentucky bourbon might be Buffalo Trace in Frankfort, located about 21 miles northwest of Keeneland.
Where to Sleep
Lexington offers the usual array of comfortable, national-chain hotels, with the downtown Hyatt sticking out as a particularly happening locale. But for a locally flavored, boutique experience, 21c Museum Hotel is within walking distance of virtually everything — save for the track itself, which is about six miles west of downtown on Versailles Road. With such a short meet, however, weekend space can get tight, making Airbnb an option worth considering.
At Keeneland, if Ken and Sarah Ramsey have a horse entered in a race, bet against it at your peril. The Ramseys are perhaps North America’s most bankable owners, and their charges are often the chalk. As for horsemen, while any number of big names are liable to mount a month-long residency at Keeneland, Julien Leparoux, Ricardo Santana Jr., and Robby Albarado are the track’s most reliable riders, while Steve Asmussen, Mark Casse, Mike Maker, Graham Motion, Wesley Ward, and Kenny McPeek typically rank among the more successful trainers.
It sounds sentimental, but Lexington might be America’s friendliest city. Whereas in Portland, Ore., there’s a whiff of smugness in the air, Lexingtonians seem genuinely eager to share their city with visitors, and the hospitality carries over — and then some — to the track. And, lo and behold, Keeneland’s not the only live bet in town, as the Red Mile — one of America’s oldest tracks, dating back to 1876 — offers twilight harness racing in August and September.
This feature was originally published in 2014 and has been updated.