Capitol building in Frankfort, Kentucky.

8 Must-See Historic Towns in Kentucky

Kentucky offers tourists a dose of history by the boatload. Some might imagine the state is all bluegrass and rye, but they would be wrong. The state was first joined with the Union in 1792, bringing with it everything we know and love about Kentucky, not the least of which being its towns. Kentucky is rich with diverse architecture and influences blended across its hundreds of years of history into the gem it is today. From the enduring icon that is Colonel Sanders to the fertile farmlands' past and present, Kentucky remembers its humble beginnings. If you are looking for someplace where its history has been lovingly linked to its present, look no further than these historical towns in Kentucky.


Bellevue, Kentucky across from Cincinnati, Ohio.
Bellevue, Kentucky, across from Cincinnati, Ohio.

The town of Bellevue is only a few minutes away from the town of Newport but successfully maintains its small-town charm and appeal. Bellevue sits on the banks of the Ohio River and calls on passersby en route to nearby Dayton and Fort Thomas to stay a while and visit its well-maintained historic architecture. This charming Kentucky River town centers on Fairfield Avenue, which leads through its historic district and towards the vicinity of buildings like the Taylor Mansion.

Saloons, opera houses, and livery stables could be found in Fairfield in the 19th century, and the town continues to work hard to revitalize this area’s buildings for future enjoyment. The Sacred Heart Roman Catholic Church is a standout and definitely worth seeing. Today, the town is known for its food and drink. the Three Spirits Tavern is a quaint watering hole where thirsty urbanists can stop and refresh themselves at a stop considered part of the bourbon trail. Burger lovers will want to swing by the Elusive Cow for a locally sourced bit to eat.


Historic commercial buildings in downtown Winchester, Kentucky
Historic commercial buildings in downtown Winchester. Image credit Christopher L. Riley via Wikimedia Commons.

The town of Winchester was placed on the National Register of Historic Places in 1981. Perhaps better known as the birthplace of Bear Cheese, Winchester is plainly historic and clearly proud of the fact. Its business district is largely unchanged from how it looked nearly one hundred years ago, featuring its five globe lamp posts and an elevated sidewalk. Besides the charming town, Fort Boonesborough State Park makes for a lovely escape into nature and its pioneer history.

Speaking of history, the Bluegrass Heritage Museum is housed in the historic Guerrant Mission Clinic and Hospital. The building itself is a delight, much like the Civil War Fort at Boonsesboro, which Union soldiers built. Clark County Public Library features gorgeous red brick construction and well-manicured grounds, and the Holly Rood mansion, built in 1814, can be explored on a guided tour.


Treble Cycle sculpture by Mike Welch outside the federal building, Danville, Kentucky. Image credit View_Point via Shutterstock
Treble Cycle sculpture by Mike Welch outside the federal building, Danville. Image credit View_Point via Shutterstock

Danville is the idea destination for those interested in exploring Kentucky’s history. The town was the official site of Kentucky’s birthplace, hence Danville’s name, the City of Firsts. Kentucky’s state constitution was first signed in 1792 at a site now known as Constitution Square. The site features historic cabins, buildings, and monumental sites of Kentucky history. The site is a state park and is open for exploration today. Danville was also the site of the first U.S. Post office west of the Allegheny Mountains.

Danville was the site of the first law school, the first capital of Kentucky, and the first state-sponsored school for the deaf. It was also the site of the first successful surgery to remove an ovarian tumor. Many of these sites are still open for visiting today, and some are still operational, like Penn’s Store in the southwestern part of Boyle County. This corner store is straight out of central casting for rustic Americana and has been open since 1850.


Paxton Inn in Washington, Kentucky.
Paxton Inn in Washington, Kentucky. Image credit Greg Hume via Wikimedia Commons.

Beautiful Washington is a historic little holler found just south of Maysville. This village is truly picturesque in all the right ways. Walking down its main street, lined with stone in the old style, you will feel yourself reaching for your phone to snap photos of the town’s aesthetics. Past the red brick buildings and between the businesses with their wooden clapboard and shingle siding, one gets a sense of how things used to be. Washington has a deep respect for its history and nowhere is that more apparent than in its architecture.

The Old Baptist Cemetery just outside town is the final resting place for the town’s founders, many of whom were Revolutionary War soldiers. The town itself was first named after George Washinton, and many of the log cabins, like Mefford's Fort, are still standing from the town’s founding in the late 1700s. Harriet Beecher Stowe famously visited the town and witnessed a slave auction on Washington’s Old Courthouse Lawn. The source of her inspiration, the lawn, remains well preserved as an example to all those who visit the town.

Horse Cave

An orange scooter passes by the historic main street in Horse Cave, Kentucky, via Robin Zeigler /
An orange scooter passes by the historic main street in Horse Cave. Image credit Robin Zeigler via Shutterstock.

The town of Horse Cave got its name thanks to the sinkhole found on the south side of its main street. Many theories exist as to why the cave was named this way, including its usage by outlaws as a place to stash horses; others involve the 19th-century usage of the term horse as a term to mean anything large. Within Horse Cave is a stream that was used to power a dynamo, which provided electricity to the town, making it one of three in the state to have electric lights.

The cave also features the world’s longest underground suspension bridge, which brings visitors to an often-frequented underground cave known as the Sunset Dome. Horse Cave has more than 50 buildings on the National Register of Historic Places in town. There is even an annual heritage festival hosted in town each September, bringing out antique tractors and artisans. Looking for more Horse Cave history? The town even features a cell phone walking tour to teach visitors about the town’s rich heritage.


Frankfort, Kentucky, town skyline on the Kentucky River at dusk.
Frankfort, Kentucky, town skyline on the Kentucky River at dusk. 

The capital of the Commonwealth of Kentucky is chock-full of historic buildings, artifacts, and history. Truly, it is hard to go anywhere in Frankfort without stumbling upon the city’s history. Kentucky’s favorite founding father, Daniel Boone, is memorialized in Frankfort just off of the town’s main street. The Liberty Hall Historic Site is a Federalist home designated as a national historic landmark in 1971. The Old State Capitol Building harkens back to the city’s center of political goings on until 1910.

The new state capitol is found on Capital Avenue and is an absolute stunner, called by many one of the loveliest in the country. The Switzer Covered Bridge, built in 1855, is a gorgeous example of the Howe truss design and is eminently photographable. The Grand Theatre in Frankfort is not only a wonderful place to catch a show, but the building’s architecture itself is incredible. Stop by any of these sites to dive into some of the living history Frankfort has to offer.


Historic buildings in the downtown district of Paducah, Kentucky. Image credit Angela N Perryman via Shutterstock
Historic buildings in the downtown district of Paducah, Kentucky. Image credit Angela N Perryman via Shutterstock

William Clark, one-half of the famed explorer duo Lewis and Clark, actually designed this lesser-known Kentucky gem. Paducah flourished thanks to its position along the river, and its name came from Comanches who were once called the Padoucas. Paducah has so much of its history captured in its murals. The town has over 60 life-sized murals by Robert Dafford that capture moments and snapshots from its past.

All of these museums are within walking distance from each other, much like the town’s museums. Moving along, walking to the Inland Waterways Museum and the Lloyd Tilghman House & Civil War Museum, where Paducah’s heritage is on display is a great way to spend an afternoon. The town’s downtown and main street are consistently called some of the prettiest in the nation. For a novel way to see the city in style, hire a carriage or ride a free trolley!

La Grange

Evening at La Grange, Kentucky
Evening at La Grange, Kentucky.

Besides being eminently historical, the town of La Grange has to be one of the most unique places in the country. Lancing through the heart of town up to 30 times per day are freight trains, the only such arrangement in the nation. Visitors to the town are often struck by the rumbling train rolling past as they explore La Grange’s quaint downtown, an unmistakable juxtaposition of old and new, which is the town’s specialty.

The town’s historic district is home to historic buildings, including hotels and train depots, and the preserved homes of La Grange’s notable citizens. A special point of interest is the Renaissance Revival-style Courthouse. Follow the walking guide the La Grange’s Historic Preservation Commission produced to experience the town like a local.

Given its vast Appalachian mountain ranges and penchants for producing some of the best bourbons around, you might be forgiven for making a beeline for Kentucky’s natural splendor or the famed bourbon trail. The state is replete with historical significance, however. Beautiful brickwork buildings and pioneer-style structures have been carefully preserved and kept as a form of living, breathing Kentucky history. Between bluegrass shows and hiking trips, make sure to carve out some time to learn about Kentucky’s storied past. There is no better way to do so than straying from the beaten path.

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