Main Street of Midway - a small town in Central Kentucky. Editorial credit: Alexey Stiop / Shutterstock.com

7 Charming Old Railroad Towns In Kentucky

Kentucky is recognized across the country for its whiskey, bourbon, Thoroughbred horses, and the legendary Kentucky Derby. But an underrated facet of the state is its close ties to the railroad industry, and the small historical railroad towns that are just as important as any specially made bourbon. Bearing the stamp of "Kentuckian," these towns saw the state flourish, and while the railroad industry has evolved over the years, the love and history of its heyday still linger around the towns it helped to build. For that reason, here are 7 charming old railroad towns in the Bluegrass State.

Ashland

The Ashland Amtrak Station was built by the C&O Railroad in the 1890s as a freight house.
The Ashland Amtrak Station was built by the C&O Railroad in the 1890s as a freight house. By Nyttend - Own work, Public Domain, Wikipedia.

Though first inhabited in pre-colonial times by the Shawnee and various other older native groups that made Adena Culture, the story of Ashland really begins not with its direct settling by Europeans, but down the line when Richard Deering discovered iron ore on his property. From then, the 19th and early 20th century breathed life into Ashland, and as the discovery of precious resources brought more people, so too did industrialization give new ways of transportation. Thus, Ashland became a railway town where transportation by cart and railway met the Little Sandy River.

Central Park.
Central Park. CC BY-SA 2.5, Wikipedia.

Today, Ashland has not forgotten its history of iron and transportation, as a trip to Broadway Square (downtown) still has historic buildings after historic buildings, such as the First Presbyterian Church, and the Community Trust Bank, which was built in 1923. Near Broadway Square, the Ashland Train Station is still operating to this day, and can be ridden like it was in the early 1900s (albeit with restored furnishings paid for by the town).

For those looking to take a quiet break, however, Ashland's own Central Park is perhaps its most famous claim to fame. Once sold to the town in 1900 by the Kentucky Iron Coal and Manufacturing Company, this 47-acre wonder is home to numerous recreational activities and even has its very own Indian Mounds. The park is easy to locate since it sits right in the center of town.

Richmond

Madison County courthouse, Richmond.
Madison County courthouse, Richmond. By FloNight (Sydney Poore) and Russell Poore - self-made by Russell and Sydney Poore, CC BY-SA 4.0, Wikipedia.

Richmond may seem like a rather unsuspecting town until one takes a closer look. Founded in 1798 by a colonel who participated in the Revolutionary War, Richmond has seen various figures throughout history walk its streets, including that of Cassius Marcellus Clay, an early abolitionist who campaigned in town for the equal rights of African Americans. And while Richmond did not depend so dearly on the railroad as most other towns had, the CSX Railroad runs through town today, which qualifies it as an albeit late railroad town starting from the 1980s and early 90s onward.

For the history buff, Richmond runs the White Hall State Historic Site, which belonged to the aforementioned Cassius Marcellus Clay, who was also the U.S. ambassador to Russia and a good friend of Abraham Lincoln. The home on its grounds is a 17th-century manor with much of its furnishings from the 18th century, when it underwent various additions and remodels. This 44-room wonder is open to the public in the form of a museum and often hosts various events and tea times for those in Madison County.

If that isn't enough, and for those looking for a more natural experience, River Hill Ranch's virtue and philosophical message may be for people: live simply, and come see some alpacas. Yes, River Hill Ranch is a humane ranch that offers some wonderful tours where the primary animal is the humble and fluffy alpaca (and they can be pet and interacted with when the handler gives the okay). As strange as it is therapeutic, the ranch hosts public yoga sessions among the alpacas. It would almost be wrong not to take them up on their offer, if not for the yoga, to at least see and pet the lovable animals.

Bardstown

The Main Street in Bardstown, Kentucky.
The Main Street in Bardstown, Kentucky.

Also known as the Bourbon Capital of the World, the people of Bardstown have been making bourbon since 1792. Pair this with Maker's Mark Distillery, the oldest continuous-operating bourbon distillery in the nation, still on its original site, and one can see the appeal left by Bardstown on the public consciousness. And while there are plenty of distillers and finely aged bourbons of quite a variety, the side of Bardstown that deserves a closer look is its railroad experience and other novelties.

Firstly, the My Old Kentucky Dinner Train is a fine dining experience fit for a king but available to anyone. The idea is that, like in the days of the 19th century, a train ticket would be purchased, and with that comes a relaxing train ride into the countryside. The higher-class trains would usually serve meals and beverages on board, and this is the spirit in which the MOKDT seeks to preserve. It is high-class dining that comes with full service, an almost three-hour train trip, and plenty of lunch and dinner excursions, including a murder mystery and a bourbon exclusive trip. Serving up novel experiences since 1988, it could be said that Bardstown's significance as a railway town is relatively recent.

Keeping in line with the Old West, the Jailer's Inn Bed and Breakfast is one of those curious places not found anywhere else. It is not a B&B that was built to replicate an old jail; it actually was the Old Nelson County Jail from 1797 to 1987. Rumored to be haunted, the rooms and furnishings are strangely comfy, with the exception of the jail cells themselves, where guests have the option to sleep behind bars, prisoner style.

La Grange

The Flying Duchess, a restored British steam engine, is on display at the La Grange Railroad Museum in Kentucky.
The Flying Duchess, a restored British steam engine, is on display at the La Grange Railroad Museum in Kentucky.

Once named "The Crossroads," the soon-to-be town was a rest stop between major hubs of trade like Louisville and New Castle. In the 1850s, long after its name became 'La Grange,' both the Frankfort and Louisville Railroad lines had stops in the small town. Thus, La Grange would see itself become part of a larger network of trade, and with that would come growth.

A mainline CSX train track runs down the middle of Main Street in historic La Grange, Kentucky.
A mainline CSX train track runs down the middle of Main Street in historic La Grange, Kentucky.

Nearly 180 years later, La Grange still prides itself on being a town brought to life by the railroad, and much more. It celebrates its history with places like the La Grange Railroad Museum, which is the only place in Kentucky that has a train running directly through its streets.

The area is also known for its natural beauty, as nearby is Falling Rock Park, a swimming hole and local secret with crystal clear waters that is perfect for snorkeling and tubing. The commitment to protecting these spring waters goes as far as a ban on alcohol to preserve the area as best as possible.

Midway

View looking west from intersection of Highway 62 and Main Street.
View looking west from the intersection of Highway 62 and Main Street. CC0, Wikipedia.

Midway's railroad origins go further back than most, as Midway was the first town founded by a railroad in the state, being founded in the 1830s. Railway workers needed a place for lodgings, and by then the Lexington and Ohio Railroad was already established, so slowly but surely, Midway became a progenitor of the railroad town as workers, passersby, and stagecoach passengers made their journey along the "Middleway" between larger towns.

Midway features a variety of activities and other cultural legacies. Double Dan Horsemanship, for example, brings the art of the equestrian kind to life with a variety of horse shows, ranch tours, and even private viewings for families and individuals. Liberty Horse Master Dan James, the owner of the ranch, is a world-famous trainer who continues to raise, breed, and train horses for shows and photo shoots to this day. His shows attract many to Midway, and likely will in the foreseeable future.

Another legacy is the Equus Run Vineyard & Winery. It's situated in the middle of the valley, surrounded by Thoroughbred horse farms. The vineyard itself is 38 acres, and while it is open for weddings, parties, and other events, wine-tasting and tours are a daily occurrence. Open year-round, the vineyard is another prime example of Kentucky soil producing very fine grapes for wine.

Bowling Green

The college town of Bowling Green, Kentucky.
The college town of Bowling Green, Kentucky.

Having deep ties to the American Revolution, the area where Bowling Green would come to be has been inhabited by settlers since 1775. The strange name of 'Bowling Green' comes from a green patch of land in New York City where revolutionaries had apparently torn down a statue of King George III and used its metal to make bullets. Later in the 1830s, the building of the Portage Railroad allowed commerce to run smoothly, and the isolated town stuck in the 1700s would begin to look more modern. Industrialization then allowed the town to excel at both transportation on land and, because of the Barren River, by water too.

L&N Train Depot.
L&N Train Depot. By OPMaster at English Wikipedia, CC BY 2.5, Wikipedia.

The Historic Railpark and Train Museum captures in little snapshots what the technological turning point of the town was like. It is a fully-fledged railyard that saw about 20 trains in its heyday, and while the trains no longer run, the exhibits and frequent events held by the museum ensure that a trip is different every visit. Perhaps one of the greatest allures to Bowling Green, not including the stunning and sleek displays at the National Corvette Museum, is the Lost River Cave. Featuring the only underground boat tour in the entire state, the cave is as beautiful as it is wondrous and mysterious. With 200,000 annual visitors, Lost River Cave is a standout place that has done much for Bowling Green's reputation.

Frankfort

A train track runs down the centre of Broadway Street in historic Frankfort, Kentucky.
A train track runs down the centre of Broadway Street in historic Frankfort, Kentucky. Editorial credit: BD Images / Shutterstock.com

The underrated capital of Kentucky is a one-of-a-kind and charming town, to say the least. There is no shortage of famous figures who rest at the Frankfort Cemetery (including Daniel Boone), no shortage of famous distilleries (like Castle and Key Distillery), and there is no shortage of historic sites that the town has accumulated over the years. A little-known fact about Frankfort, however, is that it indeed is a railroad town. The Frankfort Union Station was used by passenger trains well into the 1970s, and was occupied by the Louisville & Nashville, Chesapeake & Ohio lines for decades. It may be correct that the capital never saw it as a primary part of its identity, but for all intents and purposes, the railroads ran in Frankfort for the better part of 120 years (1850s to the 1970s).

Looking south down St. Clair Street.
Downtown Frankfort, Kentucky. In the heart of the Central Frankfort Historic District. By Kenneth C. Zirkel - Own work, CC BY-SA 4.0, Wikipedia.

So, this capital deserves its name among its fellows, additionally because of the sheer number of attractions and important sites to its name. One of these is Cove Springs Park, which has 240 acres of springs, woodland, streams, waterfalls, and forested ravines. Its waterfall near the entrance is especially picturesque, as thousands of gallons of rushing spring water fall into the man-made ravine below. And while Frankfort itself may be underrated, the same cannot be said about the fame of Cove Springs Park.

Why These Towns?

These charming towns are a perfect representation of Kentucky's history, and while some are more important in the historical record than others, none could exist as they are without the lifeblood that was the boon of the railroad industry. It was the miles of steel and decades of manpower that managed to stitch together the most desolate hamlets and settlements and create full-fledged hubs of transportation that would help usher in the 20th century—these towns are its product, and the seven above are perhaps the most charming kind that they could have ever produced. For that reason, they are worth mentioning and visiting, for there is little that can hope to rival their timelessness and niceties.

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