Situated Between Lexington And Frankfort Is 'Kentucky's Most Underrated Town' Full Of Charm

Long before the advent of mass production and personal cars, industrial trains trundled through the virgin lands of the New World. Kentucky's bluegrass seas stretched out unblemished, horse-drawn carriages rattled over the remote roads that linked the state's earliest cities, and one town sprang up to service the railway that was pioneering trade across the newborn nation. Midway was the first town in the state to be founded by a railroad company, entirely structured around the industrial innovation that was sweeping the world in the early 1800s. A midpoint for the transit of tobacco, corn, cattle, and soy, as well as Kentucky's prized horses, Midway's honest, blue-collar origins placed it at the heart of the state's early development. Today, the small city is better known for its thoroughbred horses, picturesque farms, and vibrant center, a combo that has earned it the accolade of "Kentucky's most underrated town."

From Lexington's Blue Grass Airport, it's only 20 minutes by car to Midway. Connected to 18 U.S. cities by direct flight, the airport couldn't be more convenient for travelers seeking to escape the big-city bustle. Plan a route through the bucolic bluegrasses that span the stretch between Lexington and the state capital, Frankfort, stopping off in Midway. Alternatively, travel slightly farther to Shelbyville, another bustling city situated between Lexington and Louisville offering "a perfect Kentucky getaway," to round out an equine adventure or bourbon trail in the state's central stretch.

Small and quaint, Midway is not a vast metropolis primed for endless exploration. Instead, travelers should depart on day trips to the remote rural pastures that span out from its edges. The heart of Kentucky's horse country is filled with small towns and rolling hills, and Midway's reputation for thoroughbred breeding makes a trip out to a stud farm a worthwhile venture. Visit the stomping grounds of Kentucky Derby champions on a tour of Airdrie Stud or roam through the 3,300 acres of unspoiled Kentucky countryside on Lane's End Farm. Considering the state is famous for hosting the bourbon capital of the world, it's no surprise that a number of rurally located distilleries share the rolling hills. Organize a tour and a tasting at Frankfort's Castle & Key Distillery to try out the local delicacy in a unique, rural location convenient from Midway.

While outside of the town, visitors also have a chance to learn about the millennia of history that developed here prior to the arrival of European colonizers. Underneath the area's modern farms, native Mound Builders constructed several structures, earthen-work effigies overtaken by the earth since their construction in 500 B.C. For more Native American history in Kentucky, take a trip to one of the most iconic national parks on the East Coast, a two-hour drive away.

Spanning alongside the railroad that once ruled the settlement, Midway's charming shopping street touts handmade wares, equine accessories, Kentucky-themed knickknacks, and bouquets of native flowers. Most of the town's unique, individual-owned stores and small businesses are located along Main Street, the road constructed around the old rails, which is included on the National Register of Historic Places.

Many of the town's best restaurants are also situated nearby. Sit al fresco at the French-inspired Heirloom to share an array of small plates, or fill up on pizza and burgers at The Goose & Gander. If you're more inclined to stick to unfussy Kentucky classics, grab a hearty meal and a creative bourbon cocktail at the historical Blind Harry's.

Travelers visiting in September are in for a particular treat, as the Midway Fall Festival descends upon the town each year. During the festival weekend, local craftspeople put on demonstrations of traditional regional artisanal techniques, musicians from across Kentucky blast live music for the milling crowds, and local vendors dish up tempting street food snacks.