Nestled in the elbow of northern Woodford County, it’s hard to imagine sleepy Midway as a bustling hub, but back in 1830, when the Lexington and Ohio Railroad was incorporated, it became just that — the state’s first town to be founded by a railroad.

Perhaps this is why locals don’t seem to mind that the railroad runs through the heart of downtown, which has undergone a revitalization since a Main Street Kentucky streetscape renovation project breathed new life in this postage-stamp-sized bedroom community in 2003.

Rising up, like out of a Norman Rockwell painting, from the surrounding older buildings is the vibrant, polished downtown. With ample parking and welcoming storefronts that range from an old-time soda fountain/pharmacy to trendy women’s clothing and jewelry stores, the area almost feels like a set in a movie (perhaps “Blazing Saddles” in technicolor).

With no detail spared, from lighting features and handicap accessibility to new period structures, downtown Midway is home to a mere 1,600 people and a blur of color and life. Located farther away from Lexington than county seat Versailles, its local farms produce tobacco, corn, cattle and horses.

When traveling, be prepared for delays if you take scenic U.S. 421 South, as a paving crew has the road restricted to one lane for nearly a mile.

If you’ve got the time and a good album to listen to, take U.S. 421 South and turn right onto Midway Road. Follow signs to downtown district. Continue on U.S. 62 and turn left onto U.S. 60. Turn right onto Elm Street and follow McCracken Pike to Woodford Reserve Distillery.

Continue north on Ky. 1659 to Millville. Take Ky. 1681 north to U.S. 60 back to Frankfort.


Three Chimneys Farm, a 40-year-old major thoroughbred breeding operation, has been home to a number of famous horses, including Seattle Slew, Chris Evert, Silver Charm and fan-favorite Smarty Jones.

Another local attraction, snuggled on the banks of South Elkhorn Creek, is Weisenberger Mill, which has been owned and operated for six generations. Listed on the National Register of Historic Places, it has been running since 1865, making it the oldest continuously operating mill in Kentucky.

About five or six songs west on U.S. 62, left on U.S. 60 then right on 1659, Woodford Reserve Distillery offers tours, a gift shop and tastings for bourbon enthusiasts. Glenn’s Creek Café is open daily in the visitors center.



The best part of Midway’s near obscurity is there is no excuse necessary to hop onto Interstate 64 East or US 421 South. The town’s unofficial motto, “Meet me in Midway,” is the perfect way to visit the trendy, off-the-beaten-path downtown.

A decline in railroad fortunes led to a downtrodden downtown district until the mid-1970s, when artists opened galleries and antique dealers set up shop, launching the Midway Village Guild.

Nowadays, Historic Midway has a reputation as one of Kentucky’s favorite spots for antiques, crafts, gifts, restaurants and clothing.

The city’s unique history and atmosphere is preserved by freight trains that make use of the active tracks running through Railroad Street.

With a nod to the town’s humble beginnings, Railroad Drug & Old Time Soda Fountain is centrally located smack dab in the middle of East Main Street.

With its sleek countertops and retro look, the store at first appears to be only a soda fountain, a hangout for both old and young alike. In fact, no matter the time of day, there always appears to be at least one person occupying a seat at the counter. (And, odds are, it’s a different person each time.)

The store also serves as a full-scale pharmacy, which is run out of the back of the store.

Railroad Drug & Old Time Soda Fountain is open Monday-Friday from 9 a.m. to 6 p.m. and Saturdays from 9 a.m. to 1 p.m. It is closed on Sundays.

Farther down the street sits Steppin’ Out Boutique, which offers unique ladies apparel and accessories such as jewelry, purses, shoes and hats. It also sells Kentucky Proud products — gifts made by Kentucky craftsmen using Kentucky products.

This unique boutique is open from 11 a.m. to 7 p.m. on Mondays, Tuesdays and Wednesdays. On Thursdays, Fridays and Saturdays, it is open from 11 a.m. to 5 p.m. It is closed on Sundays.



In the market for some grub? With all the dining options in Midway, even the pickiest taste buds will find something to nosh on.

The Brown Barrel and Blind Harry’s offers casual open-air dining and a takeout option. Named in honor of a beloved visually impaired grandfather, Harry Clay Anderson, the child-friendly restaurant is located on the very spot where bourbon was first distilled in 1865.

Diverse menu offerings are sure to please any palate: steak, fish, Southern-style crab cakes, burgers and pork-belly sandwiches. Soup, salads and a vast array of appetizers are also featured.

Chef and restaurateur Mark Wombles’ Heirloom Restaurant and Mezzo Italian Café, both located conveniently on East Main Street, offer unique dining experiences. Heirloom serves up eclectic cuisine such as poached chicken breast, halibut, watermelon radish and corn salad.

Mezzo Italian Café focuses on an elevated-casual atmosphere. Wood-fired pizzas are the restaurant’s specialty. Sandwiches, entrees, salads and appetizers are also offered. A local favorite, the “Meat Me in Midway” pizza features prosciutto ham, fennel sausage, olives, house-made mozzarella, salami and pomodoro tomato sauce.

Darlin’ Jeans Apple Cobbler Café sits beneath the looming Midway water tower and serves up American fare. The “Midway Chick,” a grilled chicken breast sandwich smothered in barbecue sauce and topped with bacon, provolone and mozzarella cheeses, is a featured menu item.


In mid-September, the cozy town opens its arms to visitors from around the globe for its annual fall festival. The festival features crafts, food, demonstrations, entertainment and children’s activities. Named one of Kentucky’s top 20 festivals, the event will mark its 44th year in 2018.

Presented by Midway Renaissance, Francisco’s Farm Arts Festival, planned for May 19-20 is an outdoor, open-air, juried fine arts and crafts show that kicks off the unofficial start of summer in the Bluegrass. Midway University, 512 E. Stephens St., hosts the event.

Sparks in the Park,” held each Independence Day at Walter Bradley Park, is a community wide party with a down-home feel.


Located not much more than a stone’s throw from Frankfort, Midway is worth the drive for its unique local flavor.