The 13 Best Documentaries About Kentucky

Aug 26, 2023 | Best Of, Culture, History

If you’re looking to explore the rolling hills, expansive bluegrass fields, and vibrant culture of Kentucky, there’s no better way than through documentaries. From revealing looks at the state’s turbulent history to captivating tales of its most beloved characters, Kentucky-based documentaries offer a unique glimpse into the inner workings of this special corner of America. In this article we’ve selected some of the best documentaries about Kentucky, each with its own unique perspective and story to tell. So get ready for a journey through the Bluegrass State! Whether you’re an armchair traveler or a native Kentuckian craving a bit of nostalgia, these films are sure to provide plenty of entertainment, education, and inspiration. Let’s take a look at some of the best Kentucky-based documentaries available today. From an exploration of the life and times of Kentucky native Colonel Sanders to a journey into the land of southern hospitality, these documentaries offer unique insight into this legendary American state.


1. Straight Up: Kentucky Bourbon

The Bluegrass State has long been renowned for its award-winning spirit. For centuries, Kentucky has perfected the art of whiskey making, and is now considered to be the undisputed Bourbon Capital of the world. The story of this remarkable state’s rise in the industry is one of innovation and dedication. From small family distilleries to major players like Jim Beam and Maker’s Mark, Kentucky has developed an impressive repertoire of spirits over the years. With its unique terroir and history of craftsmanship, it shouldn’t come as a surprise that some of the world’s finest bourbons can be found in this small corner of the country. From documentaries about how these renowned beverages are made to those that explore the incredible culture surrounding them.


2. The Poorest Place In Kentucky

The road we take is a winding one. We travel through some of the most isolated parts of Kentucky, where poverty reigns and has done so for generations. But it’s not only poverty that binds this place together. It’s the culture, values, and unique view of success that makes it home to those who live here. It’s a far different way of life that is rarely seen or understood by the outside world. We’ll visit big cities too, though they are big for Kentucky’s standards. We will also witness life in these winding mountain roads during the coldest time of year. For some here, this will be their first ever trip beyond what they know and love.


3. Best Documentary

The historic state of Kentucky has a unique and vibrant wine culture. With its distinctive terroir, the wines produced in the area have been celebrated for generations. In recent years, the Bluegrass State has become a top destination for winemaking with an increasing number of vineyards popping up all over the place. For anyone interested in visiting these vineyards, or learning more about the unique history of Kentucky wine, there are a few documentaries that will give you all the information you need. From tales of ancient grape-growing traditions to modern-day winemaking methods, these documentaries provide a fascinating look into the world of Kentucky’s wine industry.


4. 10 Places in Kentucky

Welcome to the Bluegrass State! Kentucky is famous for its fried chicken, bourbon, and being the birthplace of the cheeseburger. But there’s a lot more that makes this midwestern state such an amazing place to live. Not only does it boast a cost of living 21% cheaper than most US states, but its beautiful rolling hills provide plenty of outdoor recreation opportunities. Unfortunately, 20% of the population lives in poverty here too. That’s why we’re taking a closer look at Kentucky and exploring its worst cities so you can make an informed decision about where to settle down. From crime-ridden streets to struggling schools, these areas aren’t places for tourists! But don’t worry – there are still plenty of great places to call home in the Commonwealth. Let’s go on a journey to discover all that Kentucky has to offer!


5. BEARILLA: The Kentucky Cryptid That Kills

Deep in the heart of Kentucky, an enigmatic creature lurks in the woods. Natives of the area refer to it as Bearilla and fear its presence. Campers who encounter this beast speak of a large bear-like figure that stalks and hunts for sport – often targeting livestock in its path. This reclusive being has struck terror into the hearts of many, leaving a trail of destruction in its wake. But could there be more to the story of Bearilla than meets the eye? Some believe that this creature is responsible for mysterious disappearances and strange phenomena in the area – but no one knows for certain. Could it really be a beast from another world, or just an urban legend come to life?


6. The True Story of Cocaine, a Bear and a Crooked Kentucky Cop

In the wilds of Kentucky, a story emerged that changed the lives of many. The incredible tale of Blow: The True Story of Cocaine, a Bear and a Crooked Kentucky Cop tells the riveting account of a corrupt cop, an ambitious bear and untold amounts of cocaine. This compelling documentary dives deep into this unbelievable true-life narrative, exploring how it all began and how its long-reaching effects still echo today.The story begins in the early 1980s, with a Kentucky cop who had ambitions beyond his station. He set up a network of associates to traffic massive amounts of cocaine into the state, focusing on small towns where law enforcement was sparse – or easily bribed.


7. East Kentucky Flood

“In July of 2022, tragedy struck Kentucky. 45 lives were tragically lost and thousands were displaced due to the East Kentucky flood. From the perspective of those who endured this devastating event, “East Kentucky Flood” shares a moving tale of hope in the face of despair. This powerful documentary highlights both the devastating effects of natural disasters and the strength of those affected by it, making it one of the most important Best Documentaries About Kentucky. Tune in to this emotional story and witness the power of resilience in action. It will leave a lasting impact on your heart. The East Kentucky flood highlighted the economic disparities between different parts of the country, showing how even natural disasters can be heavily impacted by social circumstances.


8. 7 Best Places To Live In Kentucky

Kentucky is often overlooked when it comes to places to live in the US. However, this hidden gem has so much natural beauty and history that its potential should certainly not be taken for granted. The topography of Kentucky is quite unique – rolling hills, deep-cut valleys, and picturesque rivers all contribute to a stunning landscape. And don’t forget about the state’s economy – it is robust and provides ample opportunity for growth. In short, there are many great reasons to choose Kentucky as a home! From the beauty of its terrain to the potential in its economy, this state has so much to offer. So why not take some time to explore the best documentaries about Kentucky?


9. Kentucky – The US Explained

Kentucky is a place like no other. In its Appalachian reaches, pastures where some of the greatest racehorses train mingle with bustling port cities. From vibrant coal mining towns in the Appalachians to wide open plains along the Mississippi River, Kentucky has something for everyone. One of its claims to fame is bluegrass, a style of American music that originated in the state. But bourbon is also a major part of Kentucky culture, with some of the finest distilleries situated here. Although it has many unique characteristics, Kentucky is not just rural and rustic. It’s a vibrant mix of cultural influences from all over the United States, making for an interesting destination to explore.



Kentucky has a rich and proud distilling history which is explored in this documentary. It begins with the first settlers in 1775 and takes viewers to the sites of Kentucky’s earliest distilleries, giving them an up close look at how Bourbon whiskey-making developed over time. The production features stunning portraits and landscapes of the area, as well as original documents from Kentucky’s earliest distillers and newspapers such as the Lexington “Kentucky Gazette” and the Paris “Western Citizen”. These documents showcase how whiskey-making evolved, producing a smooth, amber-colored spirit which is now known to us as Bourbon. The documentary provides an in-depth look into this time-honored tradition of Kentucky whiskey production.


11. Kentucky Mountain People

If you’re looking for a fascinating glimpse into the lives of people living in Kentucky, then you won’t want to miss Kentucky Mountain People: And So They Live 1940 Educational Documentary! This documentary follows the struggles and triumphs of the mountain folk who lived in Eastern Kentucky during the Great Depression. Through a series of interviews and vignettes, we get an intimate look at the culture and lifestyle of these hardworking people.We witness their attempts to make a living by cutting timber, hunting, farming, and finding odd jobs wherever they can. But it’s not only work they must contend with; there is also prejudice from outside of Appalachia to deal with.


12. Kentucky’s Kaylee Whitehall case

In Kentucky, a true-crime case captivated the nation and stirred up strong emotions. It was the story of Kaylee Whitehall, a sixteen-year-old girl who vanished without a trace in April 2015. The police searched for months, but no leads or evidence ever surfaced to explain her disappearance. The mystery of what happened to Kaylee Whitehall became the focus of a documentary by award-winning filmmaker Jon Campbell. He followed the heartbreaking journey of her family and friends, as they coped with her disappearance and tried to get justice. Along the way, he revealed secrets that had never been revealed before, uncovering a complex web of lies and manipulation that surrounded Kaylee’s life right up until she vanished. This documentary, ‘The Kaylee Whitehall Case’, is still considered one of the best documentaries ever made about Kentucky and its people.


13. Kentucky Teenage Vampires

If you’re looking for a horror story that’ll make even the most hardened vampire fan scream in terror, then search no further than Kentucky Teenage Vampires. This documentary follows four high schoolers from Louisville, KY who are out to prove to the world that vampires exist. Through interviews with locals and footage of their nightly excursions it will become clear exactly what they are and what they’re after. Will the small town of Louisville be able to survive a vampire invasion? This is surely an experience that you won’t forget anytime soon!


Read On – Our Latest Top Documentaries Lists

David B