Frankfort, KY
A locally owned 1950s diner on Main Street, blocks from the Old State House, with records covering the walls and the original tin ceiling overhead. Home-cooked and made to order: breakfast all day, burgers reviewers call the best around (one arrives between two grilled cheese sandwiches), homemade pies and milkshakes. The diner runs Frankfort's week-long Hot Brown Trail each year. Open seven days from 8 am; evenings hold Tuesday through Sunday, so plan Monday as a daytime stop.
In a 19th-century brick building at 103 W Main that spent most of its life as a residence and its pub years under a series of dragon names; Frankfort natives relaunched it as Bourbon on Main in 2015. More than a hundred bourbons line the wall behind the bar, the kitchen is scratch with a range that runs from burgers to butter chicken, and the two-story deck hangs over the Kentucky River. Lunch and dinner Monday through Saturday; closed Sundays, which the diner covers. Buffalo Trace Distillery is less than two miles up the river.
Kentucky's capital — and the heart of bourbon country. Buffalo Trace Distillery (oldest continuously operating distillery in America, since 1773) is in town. Woodford Reserve sits in the rolling horse country just east. The Kentucky State Capitol (1910) is one of America's most beautiful — a French Beaux-Arts building modeled on Les Invalides. Fly the Kentucky River's deep palisades — limestone cliffs rising 400 feet from the water, hiding bourbon distilleries that have used this water for two centuries.
Bourbon — America's only native spirit by act of Congress (1964) — must by law be made in the United States, and 95% of it comes from Kentucky. Frankfort and the surrounding Bluegrass region host the densest concentration of bourbon distilleries in the world. Buffalo Trace (since 1773) is the oldest continuously operating distillery in America. Woodford Reserve (1812) sits in the rolling horse country in a National Historic Landmark stillhouse. Wild Turkey, Four Roses, and dozens more dot the landscape. From the air, the iconic white-painted warehouse complexes (where bourbon ages for 4-15+ years) are unmistakable — sometimes called "the most architecturally significant industrial structures in America."
You'll fly almost directly over this one — Keeneland sits on Versailles Road right off the end of Blue Grass Airport, less than a mile out. Opened in 1936 as a rare non-profit racetrack, its hand-chiseled limestone grandstand is widely considered the most beautiful in American racing, and Keeneland Sales is the premier thoroughbred auction house on the planet. Immediately beside it is Calumet Farm — 762 acres of red-trimmed white barns, a sycamore-lined drive, and white-bordered paddocks, the most successful operation in Kentucky Derby history with ten winners. Together, off your wingtip on departure or arrival, they're the postcard of the Horse Capital of the World.
The world's only park dedicated to humanity's relationship with the horse. Over 50 breeds on living display, the International Museum of the Horse, the American Saddlebred Museum, the Hall of Champions where racing legends are retired and visitable. The surrounding Bluegrass country — the geological alkaline limestone soil that grows the famous bluegrass that strengthens horse bones — is the densest concentration of thoroughbred breeding farms anywhere. Famous farms (Calumet, Three Chimneys, Claiborne, Spendthrift) line the perimeter. From the air, the white plank fences and emerald paddocks make a quilt unlike any other agricultural landscape.
Two miles east of the Bardstown field stands Federal Hill, the 1818 mansion better known as My Old Kentucky Home. Stephen Foster is said to have been inspired here to write the ballad that became Kentucky's state song — the one the crowd sings every year before the Derby. It became Kentucky's first state-owned park in 1923, and "The Stephen Foster Story" has played its outdoor amphitheater every summer since 1959. Bardstown around it bills itself the Bourbon Capital of the World, so the black rickhouses of Heaven Hill are right next door on the same downwind.