Things to Do in Midway, Kentucky: Main Street & Horses (2026)

The best things to do in Midway, Kentucky, are eating on Main Street, where trains still run through downtown, touring Three Chimneys Farm and visiting Woodford Reserve. Midway is a town of 1,718 people in Woodford County, between Lexington and Frankfort.

It was Kentucky’s first railroad town. In 1835 the Lexington and Ohio Railroad bought John Francisco’s farm, laid out lots and named the streets for its officials. The original rail line still splits the business district in two.

Main Street and the Midway Historic District

Downtown Midway has been on the National Register since 1978, with Greek Revival, Gothic and Italianate buildings facing the tracks. A 2003 streetscape project under the Kentucky Main Street program added period lighting and brought the storefronts back. Several restaurants sit within a block on East Main.

★ Good to know The Midway Business Association’s site lists shops, restaurants and rentals, so check it for who’s open the day you visit.

Holly Hill Inn

Chef Ouita Michel’s restaurant is on North Winter Street in Midway, and its menus are built on fresh, seasonal ingredients from local farmers. It serves dinner Wednesday through Saturday and a traditional Kentucky brunch on weekends.

★ Good to know Reserve ahead, especially for weekend brunch.

Three Chimneys Farm stallion tour

Three Chimneys, founded in 1972, is one of the major thoroughbred farms near Midway, on Old Frankfort Pike. The tour starts with the farm’s history and then visits the stallion barn. It’s a hands-off tour, but photos are fine.

★ Good to know Tours are booked through Visit Horse Country, not at the farm gate, and you’ll be walking and standing throughout.

Midway Fall Festival

The fall festival has run for more than 50 years and fills downtown with arts and crafts vendors. Sorghum-making and pottery demonstrations show off old central Kentucky crafts. It’s one of the town’s two big street events.

★ Good to know It lands on a weekend in mid-September; check the festival site for the year’s dates.

Midway Bourbon & Blues Festival

Each June, distilleries, blues bands, local artisans and food vendors take over downtown for a day. The festival itself is free to attend. A tasting pass buys you pours from the bourbon vendors.

★ Good to know Buy a tasting pass ahead if you want to sample; walking the festival costs nothing.

Woodford Reserve Distillery

Whiskey was first made on this site in 1812, and the distillery is a National Historic Landmark. It’s known for cypress fermentation tanks, three copper pot stills and an old limestone warehouse. It sits on McCracken Pike near Versailles, a short drive from Midway.

★ Good to know Book a tour on the Kentucky Bourbon Trail listing or the distillery’s own site before you go.

Castle & Key Distillery

Colonel Taylor opened the Old Taylor Distillery, known for its castle, in 1887. Castle & Key began restoring it in 2014 and now makes its own bourbon there. It’s on McCracken Pike, the same road as Woodford Reserve, so the two pair well.

★ Good to know Book tours ahead, and plan a driver for the country roads.

Kentucky Horse Park

The state-run park in Lexington has celebrated the horse since 1978 and draws more than a million visitors a year. You can walk barn to barn to see draft horses, retired racing champions and breeds from around the world.

★ Good to know Big horse shows and events change what’s open, so check the park calendar.

Also in town

Midway University, founded in 1847 as the Kentucky Female Orphan School, is in town, and the Woodford County Public Library has a Midway branch.

When to goJune brings Bourbon & Blues, and September brings the Fall Festival. Spring and fall are the most comfortable seasons for farm and distillery tours.

How long to stayMidway itself is an afternoon and a good dinner; give it a full day or two if you add a farm tour and distilleries.

Heads upBook farm and distillery tours before you drive in; Three Chimneys takes visitors on booked tours, not drop-ins.

Getting hereBlue Grass Airport (LEX) in Lexington is the closest airport with scheduled airline service, about 15 minutes east by car.

Why is it called Midway, Kentucky?

The Lexington and Ohio Railroad founded it in 1835 at the midpoint of its line between Lexington and Frankfort. It was first named Middleway and became Midway in 1837.

Do trains still run through Midway?

Yes. The path of the original 1830s rail line is still in use and runs right through the business district on Main Street.

Can you tour horse farms near Midway?

Yes. Three Chimneys Farm, on Old Frankfort Pike near town, offers stallion tours booked through Visit Horse Country. The Kentucky Horse Park in Lexington is open to walk-in visitors.

What other Kentucky towns are close to Midway?

Harrodsburg and Danville are both south of Lexington and easy to add. See Harrodsburg, Bardstown or our full list of small towns in Kentucky.

Where to find them

Main Street and the Midway Historic District E. Main St., Midway, KY 40347 Website Directions
Holly Hill Inn 426 N. Winter St., Midway, KY 40347 Website Directions
Three Chimneys Farm stallion tour 1979 Old Frankfort Pike, Versailles, KY 40383 Directions
Woodford Reserve Distillery 7855 McCracken Pike, Versailles, KY 40383 Directions
Castle & Key Distillery 4445 McCracken Pike, Frankfort, KY 40601 Directions
Kentucky Horse Park 4089 Iron Works Pike, Lexington, KY 40511 Website Directions