Where to Eat
Cheapside Bar & Grill
This reliable standby is at the center of just about everything. Inside there’s a fetching Victorian bar, all carved wood and stained glass. Outside, a usually bustling patio and the Oasis deck make for first-rate people-watching. A more-than-respectable pub menu—try the smoked turkey Reuben—and weekend bands keep the regulars coming back for more. 131 Cheapside St. (at W. Short and Mill), cheapsidebarandgrill.com
Dudley’s on Short
Ask a Lexingtonian where to eat, and you’ll quickly hear about Dudley’s. After owner Debbie Long opened in a historic schoolhouse in 1981, her establishment became a default setting for graduation dinners, proposals, baby showers, and other milestones. Long calls her menu “American cuisine with a little twist,” with a fluctuating lineup of seafood, meats, pastas, salads, and tapas-style plates such as tasty moo shu pork crepes. 259 W. Short St., dudleysrestaurant.com
The Grey Goose
The Grey Goose is one of several independent newcomers helping to reawaken a formerly moribund stretch at the edge of downtown and Lexington’s north-side historic districts. It has fast become a local favorite for at least three reasons: its unpretentious menu of sandwiches and stone-baked pizzas, its spacious, firepit-equipped patio out back, and a decent-but-not-overwhelming selection of wine and beers. 170 Jefferson St., greygoosellc.com
Holly Hill Inn
Served up inside an 1845 brick homestead with an inviting columned front porch in Midway, a hamlet just west of Lexington, chef Ouita Michel’s seasonally rotating menu manages to combine culinary ambitions with down-home goodness, giving center stage to whatever’s fresh and locally abundant. Michel (who co-owns Holly Hill and nearby Wallace Station with her husband and sommelier, Chris) has been nominated three years straight for a James Beard Award for best chef in the Southeast. Stop in for lunch, dinner, or Sunday brunch and you’ll see why. 426 N. Winter St., Midway, hollyhillinn.com
Jonathan at Gratz Park
Jonathan Lundy, another young Bluegrass-bred chef attracting national acclaim, doesn’t want you to forget for a minute what part of the country you’re in. So the dining choices in this elegant enclave inside the Gratz Park Inn are refined but always come with unmistakably Southern or Kentuckian flourishes: sea scallop hot browns, pork belly braised in Ale-8-One (ginger ale bottled in nearby Winchester), or grilled lamp chops with mint julep jelly. 120 W. Second St., jagp.info
Metropol
Housed in a narrow white-brick two-story that served as a post office in the early 1800s, Metropol has all the trappings of a splurge-meal destination, from white tablecloths to French-leaning entrees (emphasizing meat and seafood) to fine-dining prices. For all that, the vibe is more warm and inviting than stuffy, with lots of dark wood, exposed brick, and charcoal sketches of horses, jockeys, and even Laurel and Hardy. More important, the food is excellent. 307 W. Short St., metropolfinedining.com
Natasha’s Bistro & Bar
By day, this funky, airy space is a great place for a cheap lunch (with a pay-by-weight hot buffet and five-dollar specials like fish and chips). By night it becomes a smallish performance venue where on any given evening you might catch some absurdist theater, an indie acoustic or blues act, a comedy troupe, a cabaret… anything goes, including dinner (from bison burgers to vegetarian options). The mismatched decor—red Naugahyde booths, stained glass, steel I-beams, driftwood—suits an equally eclectic clientele. 112 Esplanade, beetnik.com
Track Kitchen at Keeneland
Set the alarm early to catch the Thoroughbreds’ morning workout at the Keeneland track, then have at a heaping retro plate of scrambled eggs, bacon, biscuits and gravy, and fried potatoes for five bucks and change. While munching, you’re likely to spot helmet-wearing Hall of Fame jockeys, top-tier breeders and trainers, tourists with kids in tow, seasoned track rats, or owners come to bid on future Triple Crown contenders. 4201 Versailles Rd. (across from the airport), keeneland.com
Wallace Station
Well worth the leisurely twenty-minute drive through rolling green horse farms west of town, Wallace Station serves up fresh and hearty sandwiches, burgers, salads in generous portions, and cold beer on tap. The compact premises, with a deck and lawn out back, feel as rootsy and relaxed as an old general store, which in fact it once was; it’s also served as a train depot, a post office, a Shell station, and a residential duplex. Friday nights mean a fish fry and live music by Ahab and the Whalers, a quartet of dishwashers/bluegrass strummers. 3854 Old Frankfort Pike, Versailles, wallacestation.com
Drink
Buster’s Billiards and Backroom
After its longtime home at Main and Upper streets was demolished to make way for a so-far-nonexistent high-rise hotel, UK graduates and lawyers Clark and Jessica Case reopened a much larger Buster’s last year in an 1860-vintage onetime warehouse for Old Tarr bourbon, anchoring the metamorphosis-in-progress of a crumbling industrial precinct into a nightlife hub. Since then, the cavernous space has hosted a steady stream of local acts along with name-brand touring bands. 899 Manchester St., bustersbb.com
The Horse & Barrel
A sign over the bar proclaims “World’s Largest Ultra Premium Bourbon Collection,” and in view of the evidence—a menu of well over 125 whiskeys that also nods to Canadian, Irish, and Scotch—no one’s wasting time arguing. In fact, the brain trust at Whisky Magazine recently named the Horse & Barrel one of the top three whiskey bars on earth. The Victorian environs, a deep, narrow space with a brown tin ceiling and exposed brick walls, provide welcoming surroundings in which to (gradually) work your way around the list. 101 N. Broadway, tavernrestaurantgroup.com
Skybar
This ninth-floor penthouse aerie, reflected in a skyscraper next door, offers near-wraparound views of downtown. Opened last November, Skybar is a good stop-off if you crave a little high-toned urban ambience—black-clad bartenders, black-miniskirted servers, black granite bar. You can book a lounge table for lunch or dinner or one of the three private party rooms behind etched-glass doors in the corners: bottle service available, in case your colt wins the Derby or your startup gets bought by Google. 269 W. Main St., skybarlex.com
What to See & Do
Bourbon Distilleries
Upwards of 95 percent of all bourbon comes from the Bluegrass State, elevating Kentucky to something like the Holy Land for connoisseurs. But even novices may find themselves surprisingly caught up in the sublime art of transforming corn, other grains, and Kentucky “branch water” into top-shelf hooch. The four distilleries in Lexington’s orbit, each within a half hour or so and each offering tours and tastings, are Buffalo Trace (in Frankfort), Four Roses, Wild Turkey (both in Lawrenceburg), and Woodford Reserve (in Versailles).
Historic Homes and Gardens
Lexington gets a lot of not just its heritage but also its charm from its many historic sites, open to visitors (for a fee, in some cases). A couple of those worth sampling: Ashland is the onetime estate of Henry Clay, the antebellum orator, statesman, and quintessential Kentuckian (though he was born in Virginia), who owned Arabian horses and introduced the mint julep to Washington, D.C. The Lexington Cemetery, on West Main Street, is a lush redoubt of trees, ponds, and limestone monuments where eminent Lexingtonians from Clay to UK hoops legend Adolph Rupp are laid to rest.
Horse Farms
A drive through the outlying emerald pastures and dry-stack limestone walls along Old Frankfort Pike is enough to hook anyone on horse country. But you can also get a closer look at horse breeding and training operations by touring many of the farms. Book a session with a company like Horse Farm Tours (horsefarmtours.com) or Thoroughbred Heritage Tours (seethechampions.com). Or contact individual farms such as Three Chimneys, a genteel 2,300-acre spread that’s home to retired Derby-winning stallions Silver Charm, Smarty Jones, Big Brown, and others, living the dream in plush digs that include frequent visits to the breeding shed (threechimneys.com).
Keeneland
Although less of a household name to the general public than Churchill Downs, Keeneland racetrack may be the ultimate temple dedicated to the sport of kings: an elegantly landscaped track, spacious and manicured grounds, and a courtyard paddock that could double as an Ivy League quad, all open and accessible to whoever cares to explore it. Races take place in April and October, and auctions—the largest in the world selling Thoroughbreds—are held several times annually. You can also drop in on the stately research library, where authors such as Laura Hillenbrand (Seabiscuit) have logged many an hour sifting through the archives, and where Phyllis the librarian will happily share her mint julep recipe.
Kentucky Horse Park
There’s nothing else quite like this 1,200-acre compound dedicated to all things equine. The venue for this year’s Alltech FEI World Equestrian Games, it’s a theme park of sorts celebrating horses, combining a working horse farm with competition arenas, two museums, a Hall of Champions, a farrier shop, horse-drawn trolley tours, polo matches on summer Sundays… you get the picture. Admission prices vary seasonally. 4089 Iron Works Pkwy., kyhorsepark.com
Shop
The Keeneland Shop
It’s hard to imagine that any gift shop anywhere carries more horse-themed items than this emporium tucked into Keeneland’s race track pavilion. There’s not much for Old Dobbin himself here, but all kinds of goodies for platinum-card-carrying humans: Longchamp purses, hand-painted stemware, jockey table lamps, Barbour jackets, row upon row of equestrian-motif neckties, jewelry, shelves full of horse books, horse-head flasks, bourbon balls, and a mind-boggling display of Derby-caliber women’s hats. Worth a browse even if you’ve never pegged yourself as a horse person. 4201 Versailles Rd., keeneland.com
Lexington Farmers Market
At its flagship location under a sleek glass-roofed pavilion in Cheapside Park, and spilling out onto nearby sidewalks, Lexington’s Saturday market ranks with the best. You can scope out the makings of an epic spread here: all manner of fresh-picked crops, raw honey, sustainably raised filet mignon, freshwater prawns, Bleugrass chèvre, lamb sausage, and bottles from the growing number of Kentucky wineries. Musicians flock here too, making this one of the few locales where you have a good chance of spotting a hula-hooping fiddle player. 7:00 a.m. to 3:00 p.m. Saturday. Cheapside Park, lexingtonfarmersmarket.com
L. V. Harkness & Company
“Things I see everywhere bore me,” Meg Jewett, owner of this high-end shop, has said. No danger of that here, where Jewett (who also owns Walnut Hall Stock Farm and actively supports the Kentucky Equine Humane Center) stocks all manner of housewares and objets d’art that you won’t find at any mall. If you’re in the market for an antique Peruvian armoire, a pink shot glass made of Himalayan salt, or an engraved crystal elephant decanter, look no further. If not, stop in to check out the rooftop garden dreamed up by renowned local designer Jon Carloftis. 531 W. Short St., lvharkness.com
Men’s Clothing Boutiques
Within about a two-minute walk of each other dwell two surviving members of a dwindling species, old-guard traditional gentlemen’s clothing shops. Graves Cox, established in 1888, and Howard & Miller, a relative newcomer that opened in the 1980s, each carries a wide selection of custom suits, ties, and unapologetically preppy sportswear ready for its closeup on the links or the autumn races at Keeneland. Graves Cox, 325 W. Main St., gravescox.com; Howard & Miller, 127 N. Broadway, (859) 259-3926.
Old Town Artisans Village, Berea
A forty-minute drive south of town on I-75 brings you to a mother lode of more than forty studios and galleries practically bursting with locally conjured folk art and handicrafts. Berea has been a hotbed of artisanship for more than a century. Plan your browsing around lunch at Historic Boone Tavern, a beautifully renovated inn staffed largely by Berea College undergrads. berea.com
Sleep
CastlePost
In Bluegrass country, even the county jail looks like some magnate’s plush horse barn, so why not a bed-and-breakfast in the shape of a medieval castle? An anachronism that sat unfinished in the hills just west of Keeneland and the airport for thirty years, CastlePost was rebuilt (after a 2004 fire) and reborn as a luxurious 16-guest-room inn, owned by a Miami lawyer who graduated from UK. It also encompasses a ballroom, a billiards room, a pool, tennis and basketball courts, a lavish library and music room… all in all, enough to make Louis XIV feel right at home—though this Versailles is pronounced “Ver-sails.” 230 Pisgah Pike, Versailles, thecastlepost.com
Gratz Park Inn
An inviting three-story, 41-room antidote to Lexington’s oversupply of chain hotels, nestled in a leafy historic district a short stroll away from dozens of restaurants, shops, and other diversions. This being Lexington, the hushed hallways are lined with vintage equestrian prints, and there’s a small library/game room and fitness center downstairs. 120 W. Second St., gratzparkinn.com
Griffin Gate Marriott Resort & Spa
This is Lexington’s only full-tilt resort hotel and the chain property with the most personality, about four miles from downtown on the site of—what else?—a former horse farm. Bragging points include an 18-hole Rees Jones–designed golf course, indoor and outdoor swimming pools, four restaurants and a Starbucks, and a reputable spa that offers locally flavored treatments such as an herbal Bluegrass Wrap and a Mint Julep body polish (actual julep, sad to say, not included). 1800 Newtown Pike, griffingatemarriot.com
