11 Prettiest Small Towns In Kentucky

Kentucky's small towns range from a Bluegrass capital with a flowering clock on its Capitol lawn to a coal-country community with sandstone arches above the treeline. Some are anchored by 19th-century mansions and frontier-era forts, others by the cannonball still lodged in a downtown wall from a Confederate raid. Travelers willing to leave the interstate can find moonbows over a 68-foot waterfall, freight trains rolling down the middle of Main Street, and retired thoroughbreds grazing within sight of the plant that built the first American Camry. These eleven towns make the case for a slower route across Kentucky.

Elizabethtown

Roughly 45 miles south of Louisville, Elizabethtown answers to the local nickname Etown. The downtown square mixes independent shops like Sweet Rebel Boutique with a brick wall that still holds a cannonball fired during John Hunt Morgan's December 1862 Confederate raid. A short walk leads to Freeman Lake Park, where rowboats and kayaks are available for rent and the Summit One-Room Schoolhouse, originally built in 1892, stands with its red roof and bell tower preserved on the lakeshore.

Frankfort

With about 28,600 residents, Frankfort is one of the smallest state capitals in the country. The Capitol building carries 70 monolithic Ionic columns along its exterior, and the Floral Clock on the grounds, dedicated in 1961, is replanted seasonally and collects coins tossed by visitors. Frankfort Cemetery, on a bluff above the Kentucky River, holds the marker traditionally identified as Daniel Boone's grave, though Missouri historians have long disputed whether the remains moved here in 1845 are actually his. Cove Spring Park has a short hike to a waterfall, and the Buckley Wildlife Sanctuary south of town offers meadows and woodland trails along the Elkhorn Creek drainage.

Cumberland

The town now called Cumberland was originally Poor Fork, after the small tributary of the Cumberland River it sits beside. The renamed community is the gateway to Kingdom Come State Park on Pine Mountain, where overlooks like 12 O'Clock Rock and Log Rock take in long stretches of the Appalachians and the towns tucked into the valleys below. Trails connect a small mountain lake to the Log Rock sandstone arch, and the Little Shepherd Trail follows the ridge of Pine Mountain for more than 30 miles, passing back into Kingdom Come for some of the longest views in the state. Sleepy Hollow Golf Course sits below the mountain in town.

Slade

Slade has a population of barely over 100 and serves as the front door to the Red River Gorge Geological Area, a section of Daniel Boone National Forest where the Red River has carved sandstone arches and cliff faces above the canyon floor. The Natural Bridge itself, in the adjacent Natural Bridge State Resort Park, stands 65 feet high and 78 feet long and can be reached by trail or by the park's skylift. Below the bridge, the Devil's Gulch staircase descends through a narrow rock passage. Climbers from across the country gather at Miguel's Pizza, the unofficial trailhead and pizza joint that has anchored the local climbing scene since the 1980s.

Pikeville

Pikeville sits in eastern Kentucky's coal country, in the heart of the Appalachian Mountains and at the center of the territory contested in the Hatfield-McCoy feud, which played out across Pike County, Kentucky and Logan and Mingo counties in West Virginia from the 1860s through the 1890s. The Historic Pike County Courthouse hosted the 1889 trials, where Ellison "Cottontop" Mounts was the only defendant sentenced to death and was hanged the following year. The Pikeville Cut-Through, completed in 1987 after fourteen years of work, rerouted the Levisa Fork and US 23 through a mountainside and is often called the second-largest earth-moving project in the Western Hemisphere after the Panama Canal. About an hour east, on the Virginia line, Breaks Interstate Park drops into a five-mile canyon roughly 1,650 feet deep, the deepest east of the Mississippi.

La Grange

La Grange is one of the few towns in the country where active CSX freight trains still run down the center of Main Street, passing storefronts and restaurants like One Nineteen West Main several times a day. The La Grange Railroad Museum and Learning Center keeps an L&N caboose and a vintage L&N dining car on display, the latter available for private rentals. Outside town, the Morgan Conservation Park preserves stands of Osage orange and sycamore, and the Creasey Mahan Nature Preserve protects a section of the Kentucky woodland walk that runs through Oldham County.

Corbin

Corbin sits on the southern edge of the Daniel Boone National Forest near Cumberland Falls, a 68-foot, 125-foot-wide curtain often called the Niagara of the South and one of the few places in the Western Hemisphere where a moonbow can be seen on clear nights around the full moon. Laurel River Lake spreads across the forest just to the west, with bass and trout fishing and several public marinas. In town, the Harland Sanders Cafe and Museum preserves the service-station restaurant where Sanders developed his pressure-fried chicken in the 1930s and 1940s, before Pete Harman opened the first Kentucky Fried Chicken franchise in Salt Lake City in 1952.

London

London markets itself as the Cycling Capital of Kentucky, and the Redbud Ride each spring draws road cyclists through Laurel County during the redbud bloom. Levi Jackson Wilderness Road State Park covers ground that the Boone Trace and Wilderness Road both crossed in the late 18th century, with a Mountain Life Museum and a section of the trail Daniel Boone blazed in 1775 still walkable. About 25 minutes north, the Camp Wildcat Battlefield preserves the site of an October 1861 Union victory, one of the earliest Civil War engagements fought on Kentucky soil. Laurel River Lake, also accessible from London, is one of the state's better lakes for scuba diving and rainbow trout.

Winchester

Winchester sits in the Bluegrass roughly 20 minutes from Fort Boonesborough State Park, a reconstruction of the 1775 frontier station founded by Daniel Boone on the Kentucky River. Boaters launching from the park can run the Palisades, a corridor of limestone cliffs that line both banks of the river through Clark and surrounding counties. Winchester is also the source of two Kentucky food traditions: Ale-8-One ginger ale, bottled in town since 1926 at a plant that still gives tours, and beer cheese, credited to Johnny Allman's Driftwood Inn in the 1940s and now the subject of an official Beer Cheese Trail through Clark County.

Bardstown

Bardstown sits at the heart of the Kentucky Bourbon Trail, with distilleries including Heaven Hill, Willett, and Barton 1792, the latter operating on the site of Tom Moore's 1879 distillery. Local tradition credits the Baptist minister Elijah Craig with inventing bourbon here in the late 18th century, though historians treat that story with some skepticism. Federal Hill, completed by Senator John Rowan in 1818 and now the centerpiece of My Old Kentucky Home State Park, is the Federal-style house long associated with Stephen Foster's 1853 song that became the Kentucky state anthem. The Civil War Museum complex on Old Bardstown Village's grounds includes a Women's Civil War Museum focused on women's roles in the conflict. Twenty-five minutes north, Bernheim Arboretum and Research Forest hosts Danish artist Thomas Dambo's three Forest Giants, built from reclaimed wood and scattered along the trails.

Georgetown

Georgetown is best known for two things on opposite ends of the local economy. Old Friends Farm, founded by former Boston Globe writer Michael Blowen, takes in retired thoroughbreds, including Kentucky Derby starters, stakes winners, and broodmares, and offers walking tours among the paddocks. A few miles south, Toyota Motor Manufacturing Kentucky, opened in 1988 to build the first American-made Camry, runs tram tours through the assembly plant and maintains a small biodiversity trail at its visitor center. Ward Hall, built around 1853 by planter Junius Richard Ward, is a Greek Revival mansion with thirty-foot Corinthian columns; his sister Sallie Ward, the Louisville socialite famous for multiple marriages and Parisian-couture scandals, was a frequent visitor rather than a permanent resident.

Eleven Reasons to Take the Long Way Through Kentucky

What ties these towns together is the way Kentucky packs different landscapes and stories into short driving distances. Mammoth Cave may pull the largest crowds, but a weekend in Cumberland or Slade gets you sandstone arches without the queue, and a single afternoon in La Grange, Frankfort, or Bardstown will trade Main Street trains for a Capitol lawn or a 19th-century distillery. Pick the route that matches the trip you actually want.