Main Street of Midway, Kentucky. Editorial credit: Alexey Stiop / Shutterstock.com

8 Of The Quirkiest Towns In Kentucky

Kentucky, also known as the "Bluegrass State," is a southeastern U.S. destination full of outstanding and quirky small towns that are surprising and marvellous to outsiders. With lots of commercial attractions and historical and natural landmarks to fulfill a traveler's checklist, there are plenty of opportunities in the state while taking in humid subtropical climates. These eight small towns are guaranteed to bring smiles and adventure to those needing a vacation full of interesting or unusual encounters.

Bardstown

The Old Talbott Tavern in Bardstown, Kentucky
The Old Talbott Tavern in Bardstown, Kentucky. Editorial credit: Ryan_hoel / Shutterstock.com

Bardstown, with a population of 13,895 residents, is equal parts quirky and unforgettable. With its eccentric position as the "Bourbon Capital of the World," it is not hard to discover the essence of culture in this town. The Heaven Hill Distillery, for instance, combines 1930s history and flavorful delights to create a unique experience not found elsewhere in the state. There are also the Elijah Craig and Larceny Galleries, which pay tribute to the architect of distillation in town and John. E. Fitzgerald's treasury barrels, respectively. Over at My Old Kentucky Home, tourists can check out iconic 19th-century fashion trends and horseracing history that have been around for over 200 years on the historical Rowan family plantation. Hungry tourists may enjoy the memorable Dinner Train, which caters to guests with an elaborately designed set of dining tables situated in a moving locomotive. Shoppers may be in for a treat at Shaq & Coco, a cozy furniture outlet with whimsical and unparalleled antiques. Nature lovers can stroll around Bardstown Community Park, a pavilion landmark with multiple sightseeing trails and small community events perfect for recreation and comfort. Rare and quirky finds are just the norm in this lovely town.

Shelbyville

Shelbyville, Kentucky.
Shelbyville, Kentucky. Editorial credit: Blue Meta / Shutterstock.com

This small town of 17,686 locals is known for its love for equestrianism, hence its distinction as "Saddlebred Capital of the World." The largest Icelandic horse farm in the state, Lettleiki Icelandics, is situated right in this town, making it a hotspot for European-styled horseriding and outdoor harmony. Tourists can enjoy Shelby Trails Park and West Meadow Farm as well, supposing that their itinerary includes connecting with the residents in town and petting exotic horse species. A quirky indulgence worth pursuing is the Shelbyville Fountain, a commercial downtown attraction that appeals to anyone with an interest in 1890s bronze sculpturing. The Grove Hill Cemetery landmark could also appeal to travelers who desire to learn more about genealogical research and the role that more than 18,000 people played in helping to shape the town's history today. For anyone who prefers seeing quirks within an indoor environment, the Gallrein Farms locale brings out the best fresh fruits and unusual plant life within a surprisingly sturdy glasshouse interior.

Midway

Main Street of Midway, Kentucky. Editorial credit: Alexey Stiop / Shutterstock.com.

There are plenty of quirks to witness in this historic railroad town of 1,714 residents. The uncanny Midway Watertower is a 1940s gable roof landmark dubbed "The Tin Man" because it closely resembles a character from The Wizard of Oz and is a random but worthwhile stopping point for photographers. There is also City Hall, a frequented plaza full of colorful buildings of varying shapes and sizes that appeal to anyone with a keen eye. The Equus Run Vineyards is a modernized cattle farm that doubles as a pleasant wine-tasting locale for travelers hoping to make lasting memories, mixing cozy vibes with unexpected enjoyment in a spacious public barn setting. A central Kentucky locale that seems almost located in the middle of nowhere in town, the Crushed Violet is where 1970s Italian history meets local equine fragrances, resulting in an extraordinarily quirky beauty shopping experience. For those who favor more history, newcomers can visit Weisenberger Mill Bridge, which acts as a focal point for both natural pleasures and buttermilk pancake knowledge instilled by friendly tour guides.

Hodgenville

The First Lincoln Memorial for 16th President Abraham Lincoln in Hodgenville, Kentucky.
The First Lincoln Memorial for 16th President Abraham Lincoln in Hodgenville, Kentucky.

A small town with 3,420 inhabitants, Hodgenville is a rural and charming destination worth visiting. It is most famous for being the birthplace of former U.S. president Abraham Lincoln and has become a historical hotspot for travelers wanting to explore the original foundations of political figures. While in town, one may quickly find the Lincoln Statue, which sits adjacent to the Lincoln Museum and its late 1980s quirky antiques reminiscent of the old days of American leadership. There is also the Birthplace National Historical Park, which is a 19th-century cabin exterior dedicated to Lincoln and his trusted Cabinet. For outdoor beauty at Knob Creek, tourists can experience the Lincoln Boyhood Home, where a quirky homestead is demonstrative of the town's tribute to the 16th president. Hungry travelers can check out El Acapulco for gourmet Mexican treats in an old-fashioned manner, while unconventional homecooked meals and cordial country musicians await at Joel Ray's Lincoln Jamboree. For nature enthusiasts in town, it is best to view Abe's Pay Lake and Crawford Farms Pumpkin Patch, both ushering in social atmospheres and laidback fishing spots for tourists needing a resting point while having unforgettable conversations with locals.

Frankfort

Aerial view of Frankfort, Kentucky.
Aerial view of Frankfort, Kentucky.

Frankfort is a memorable destination in Kentucky for anyone seeking quaint downtown shopping and natural sights. With 24,487 residents, the state capital is often visited for its small-sized boutique shops and bourbon whiskey, and Buffalo Trace Distillery has the best of both aspects by honoring its traditions of selling spirit merchandise and exclusive glassware that are not usually found in other small towns. Rebecca Ruth Candy Tours & Museum is an exquisite and quirky locale that is host to 19th-century chocolate, free aromatherapy services, and southern hospitality, while also being a pioneer for Bourbon Balls. Over at Buckley Wildlife Sanctuary, visitors can see avian habitats and local environments come to life with ecological workshops and 1920s hands-on plant history tours of the landmark, something not typically findable in such states. The Frankfort Cemetery is an 1840s historic site that serves as a popular touring zone for newcomers who want to see where renowned explorer Daniel Boone and his family were laid to rest, alongside other famous Kentuckians over the years. For an oddly satisfying quirky experience, the Floral Clock is a frequented spot for tourists who want to observe a flowering clock with multicolored bushes and eye-catching seasonal floral decorations.

Horse Cave

Campground in Horse Cave, Kentucky.
Campground in Horse Cave, Kentucky. Editorial credit: rchat / Shutterstock.com

This town's 2,269 inhabitants would agree that Horse Cave's glassblowing culture and geological locales are worth all the quirkiness for travelers. As the town is already situated above an entire cave system, it is quite famous for its crafty attractions and sites like the Hidden River Cave & American Cave Museum, where historic downtown entrances to subterranean rivers flow right through town and are over 100 feet below ground, generating a plethora of interest to outsiders. While witnessing random Victorian gingerbread decorations all around town, newcomers may come across rural Kentucky's National Art Museum, which features glass artistry and history that is relevant to anyone with an interest in learning more about sociocultural impacts in the town. A surreal or quirky vibe is also established at All Things by Mel, a boutique gift shop with merchandise that makes visitors feel like they are standing inside an underground chamber, something that one may not find elsewhere in the countryside while casually shopping around. For animal lovers, the Dutch Country Safari Park creates a niche landmark driving tour with cute hand-feeding activities for guests.

Rosine

Rosine Born Jamboree in Rosine, Kentucky.
Rosine Born Jamboree in Rosine, Kentucky. Image credit: Don Sniegowski via Flickr..com

A small town with only 102 residents, Rosine may be minuscule on the map but serves a greater purpose for tourism with its various historical locales and memories for travelers. The town's very own Bill Monroe Museum is a major stopping point because it references the famous musician and his musical contributions to the entire state as the "Father of Bluegrass." Rosine Born Jamboree is a quirky music venue that may seem small at first glance but, in actuality, is host to dozens of food trucks and lawn chairs that bring out the true country vibes of the town's nightlife. There is also Everett Park and its related campground, landmarks that have a long-winded walking trail that intersects at one central location and is full of bluegrass enthusiasts and soft-chirping pigeons, resulting in an unforgettable time. All of these locales prove that the town has come a long way in its development despite being lesser known to most travelers in Kentucky.

Glasgow

 South Green Street in Glasgow, Kentucky.
 South Green Street in Glasgow, Kentucky. Image credit: Ichabod via Wikimedia Commons.

A truly quirky community exists in this town of 15,410 inhabitants, and for good reason. With its Scottish influence and cultural heritage, visitors will always be comfortable with sightseeing and entertainment. In the vibrant downtown sector, the South Central Kentucky Cultural Center offers charming street eateries, while the Plaza Theatre is a featured locale with regional and national artists performing in a quirky yet cozy regal setting. The Old Glasgow Seminary Home is a historical landmark that was once an underground railroad foundation during the Civil War. The Mammoth Cave National Park is a glorious landmark with endless opportunities to see surrounding shorelines and unusual fossil findings brought out by paleontologists. Another quirky natural landmark that will appeal more to fans of floral life is the Brigadoon State Nature Preserve, which is home to 187 protected acres of spring wildflowers and rare or uncommon animal species. For even further oddities, the town's Unusual Old Trees Self-Guided Walking Tour on historic South Green Street lives up to its name, with tourists being introduced to forest growth that has a recognizable home in town.

These small towns all provide enough quirks and attractive features to entice anyone to visit Kentucky. It is only possible to live out such experiences by physically staying in these towns, so having this list in hand ensures that travelers will know where to go and how to enjoy themselves around locales and landmarks full of unforgettable moments. Historical and natural wonders are abundant when visiting America's southeastern splendors.

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