I have a bold claim, y’all: Halloween season is the best time of the year in Kentucky (other than Derby season, of course). Fall in Kentucky means crunchy colorful leaves, crisp breezy air, apple stack cake, pumpkins, bourbon, and apple cider. From scenic railroads winding through fall foliage to haunted houses to pumpkin farms and apple picking, fall in Kentucky has it all!
If you take a scenic drive through Kentucky’s rolling hills and horse country, you’ll find plenty of autumn adventure. Here’s a complete list of ways to celebrate fall in Kentucky!
Psst: We have a few other posts to help you make the most of fall in Kentucky. Check them out:
- 35 Epic Pumpkin Patches in Kentucky to Visit This Fall
- 14 Things to Do to Celebrate Fall in Louisville, Kentucky
- 11 Terrifying Haunted Houses in Louisville, Kentucky, & Indiana
- 25+ Fall Festivals in Louisville
Things to do in Fall in Kentucky
In my hometown of Louisville, Halloween is a month-long celebration that showcases what the city does best. Like a massive Jack O’Lantern art festival, terrifying haunted houses (plural, there are lots) filled with way-too-realistic professional actors wielding chainsaws and/or actual, legit ghosts, and an incredibly charming Halloween party at the Louisville Zoo.
Y’all, there’s nothing like drinking warm apple cider as you walk through miles of flickering candle-lit pumpkin art before scaring yourself silly at a haunted house in Louisville!
But in this post, we’re venturing outside of Louisville on a scenic drive through Kentucky’s rolling hills and horse country in search of autumn adventure. Here are all the best things to do in fall in Kentucky!
Ride a Train through the Foliage
Kentucky’s railways have a long, rich history and played a critical role in the development of the state. Today, several of them are still used as scenic passenger trains!
Ride Kentucky’s Big South Fork Scenic Railway through scenic vistas, hardwood forests, mountain streams and roaring rivers while experiencing the history and charm of Appalachia! You’ll take a 16 mile round trip into the Daniel Boone National Forest and Big South Fork National River & Recreation Area.
Starting in mid-October, the seasonal Shadows of Autumn: Fall Color Express train descends through a lush gorge to the historic Barthell Coal Camp. You’ll take a guided tour through the old mine, see the old Company Store, schoolhouse, and doctor’s office, as well as the McCreary County Museum.
And like, I know the historic mining town isn’t advertised as spooky, but it definitely has spooky “ghost town” vibes. Or maybe I’m just soft.
- Kentucky’s Big South Fork Scenic Railway | Address: 66 Henderson St, Stearns, KY 42647
Take a 90-minute train through scenic horse country to the banks of the Kentucky River on the Bluegrass Railroad! On Saturdays in October, the train stops at a Pumpkin Patch. Sip a complimentary cider and pick out your perfect pumpkin before hopping back on the train!
All proceeds from tickets and pumpkin sales go directly to the Life Adventure Center, a non-profit which uses outdoor adventure and the natural environment to help individuals affected by trauma cope with and overcome cognitive, behavioral, and social challenges, and build more resilient people for a better world.
- Bluegrass Railroad | Address: 175 Beasley Rd, Versailles KY
For more scenic railway rides in Kentucky, head over to this guide.
Take a Scenic Drive to see Fall Foliage
There’s nothing like driving through Kentucky’s rolling hills patchworked with horse fences and colorful changing leaves. And while most of the activities in this post will require a beautiful, scenic drive, if you want to make fall scenery the focus of your adventure, there are a few scenic drives in Kentucky that are well worth the trip!
Let’s start with a scenic drive close to Lexington. The Old Frankfort Pike Historic and Scenic Byway winds through rural landscapes, railroad stations, a historic tavern, and plenty of horse farms, barns and stables (cuz, ya know, Kentucky). But the highlight is a two-mile section canopied by gorgeous trees bursting into fall colors!
Along the way you’ll find plenty of places to pull off to eat, tour a museum or a horse farm, buy some stone ground grits at Weisenberger Mill, or spend some money at Keeneland (ahem: more on that later).
Head to Daniel Boone National Forest in eastern Kentucky to take scenic drives through bright fall foliage and looming mountains! The enormous forest cuts through the state vertical. On the northern end you’ll find the jewel of Kentucky’s outdoor beauty, Red River Gorge, and the Zilpo Scenic Byway. On the southern end you’ll find the Wilderness Road Heritage Highway. Why not drive both of them – and then tie in a trip to Cumberland Gap – for maximum foliage?
At the very southern border of the state, the Cumberland Gap Scenic Parkway is an iconic Kentucky (and Tennessee) drive. On this 50-mile route, you’ll ascend steep mountain passes, cross over Lake Cherokee, and head toward the Tennessee side of Cumberland Gap National Historical Park. Keep an eye out for historical markers that highlight the path Daniel Boone first explored in 1769!
To complete the trifecta of gorgeous Kentucky scenic byways, head to far western tip of the state to drive the Trace, aka the Woodlands Trace National Scenic Byway. You’ll be driving 43 scenic miles between the lakes. Which lakes? No, sorry, that’s what it’s called: Land Between the Lakes.
Anyway, you’ll end up in Dover, Tennessee which is just 1.5 hours from Nashville. Seems like a good excuse for a weekend trip to me! (Psst: this Nashville weekend itinerary is perfect at any time of year.)
Go Hiking to see Fall Colors
Pick a trail in Red River Gorge. I mean, any trail will do, really, but Natural Bridge, Creation Falls, and Chimney Top are all nice and short but with a huge scenery payoff – plenty of bang for your buck on a short trip! For a longer trail, try Gray’s Arch or this 5-mile loop.
While you’re here, book a cabin and have yourself an outdoorsy fall weekend getaway! Drive the scenic byways we listed above, wear your most Daniel-Boone-esque outfit (we all know the hat I’m referring to, right?) and have the coziest time ever.
- Red River Gorge | Address: Robbie Ridge Rd, Stanton, KY
What’s scarier than hiking in the dark?? But you’ll have to brave coyotes, mountain lions, and werewolves if you want to see Cumberland Fall’s mysterious Moonbow!
Time your hike just before or after the full moon to see the lunar rainbow phenomenon (here’s a helpful guide). No, I’m not just being Halloween-y, that’s literally how moonbows work. But like, you can see how this is a super Halloween-y hike, right?!
Also, for my anxiety, please pick up a strong headlamp to bring on your hike. There’s actually nothing scarier than tripping over a root, twisting your ankle, and spending an agonizing night alone in the dark, possibly with no cell service. That is literally my Halloween nightmare.
- Moonbow Trail | Address: Dupont Lodge Loop, Williamsburg, KY
Raven Run Nature Sanctuary is about 20 minutes away from Lexington and has an appropriately spooky name. The park has 734 acres bordering the Kentucky River, ten miles of trails, and stunning fall foliage!
- Raven Run Nature Sanctuary | Address: 3885 Raven Run Way, Lexington, KY
Right in the heart of Louisville, nestled among Louisville’s Highlands neighborhood is the beautiful, enormous Cherokee Park.
Winding throughout the park are well-maintained trails which criss-cross the main road and pass through dense forests and luscious hills. While many visitors to Cherokee park spend most of their time driving or walking the paved Scenic Loop, the real magic of Cherokee is found on the Cherokee Park Trail, a meandering loop that takes you through the true heart of Cherokee Park.
The trail takes you up and down rolling, forested hills, passing by oaks and tulip poplar trees, across meadows and creeks. It’s the best place in Louisville for a scenic fall hike (or drive) and a picnic in the crisp fall weather!
- Cherokee Park | Address: 745 Cochran Hill Rd, Louisville, KY
Pick Pumpkins & Apples
At Evan’s Orchard in Georgetown, KY, you can pick your own apples and pumpkins. But the real star here is the cider mill, fresh baked apple cider donuts, and fried apple pies!
- Evan’s Orchard | Address: 198 Stone Road, Georgetown, KY
Country Pumpkins in Northern Kentucky offers all kinds of family-friendly fall fun and is less than an hour away from Cincinnati. There are plenty of free activities for littles, like play areas, a Kiddie Corn Maze, hay pyramid, and farm animals.
For a little extra, you can pick and carve pumpkins, take a hay ride or cotton wagon, get lost in a four-acre corn maze, and try the Chunkin’ Pumpkin Launcher, which is exactly what it sounds like.
- Country Pumpkins | Address: 1835 Sherman Mt. Zion Road, Dry Ridge, KY
Technically, Huber’s Orchard & Winery is just across the river from Louisville in southern Indiana, but we’re gonna include it as one of the best things to do in fall in Kentucky because hey, it’s still part of Kentuckiana! Also, they have a winery, which is unique enough to make our list.
If the Spiced Apple Wine made from locally grown apples isn’t enough of a selling point, how about picking pumpkins and fresh apples, hay bale rides, and more? (It’s OK to just go for the wine, we don’t judge.)
- Huber’s Orchard & Winery| Address: 19816 Huber Road, Starlight, IN
Go on a Hay Ride
What do you get when you combine farms, tractors, and hay bales? Hayrides, of course! There’s nothing like a hayride through a Kentucky farm. The sights, the smells, the sights, the hay that gets inevitably stuck in your hair…. ahhhh.
Well, one thing’s for sure: a hayride is the best way to entertain a kid who can’t walk very fast and/or isn’t much of a fan of walking at all. Plus, it’s grandparent-friendly, too.
Most hayrides are at working farms, so there’s a high chance of overlapping hayrides with corn mazes, pumpkin patches, and other fall fun. You’ll find all the details on hayrides in Kentucky in this guide.
Attend a Fall Festival
Two words: Bourbon. Festival. Y’all, yes. Head to Bardstown in mid September to partake in bourbon sampling, a ridiculous Bourbon barrels race, BBQ, a relay, car show, rare bourbon auction (for big ballers), live music, and more.
Or just to go to drink bourbon. I mean, this is Kentucky.
- Kentucky Bourbon Festival | 114 North Fifth Street, Bardstown, KY
There are three flavor combinations in this world which bring me right back to my childhood: pecan and chocolate, bourbon and chocolate (all kids in KY eat bourbon balls growing up, right?? I’m not weird for developing a taste for bourbon at a very young age, right???), and sorghum and biscuits. Mmmm.
Even smelling sorghum will take me immediately to the Kentucky State Fair, where they used to hand out sorghum samples in front of like, a chicken incubator, I think? My memory is a little hazy, but it’s inextricably tied to the taste of sorghum on a hot, buttery biscuit.
Which brings us to the Morgan County Sorghum Festival. On the last full weekend in September, downtown West Liberty transforms into a spectacular crafters paradise, featuring local and regional artisans and crafters, talented musicians, delicious food vendors, and lots and lots of sorghum!
- Morgan County Sorghum Festival | Downtown, West Liberty, KY
Louisville LOVES its festivals, and fall is no different! There are so many fall events in Louisville to take part in, all celebrating things Louisville loves: food, drink, culture, and the arts.
For more fall festivals in Kentucky, head over to this guide.
See Kentucky’s Best Halloween Displays
You know how there are those neighborhoods that get REALLY into Christmas light displays? Like, aggressively so? To clarify: we fully plan to be those competitive a**holes in the future.
Well, there’s plenty of those people (our people) in Kentucky!
Most of Louisville goes all out for Halloween, but one street in particular celebrates the holiday like no one else. Hillcrest Avenue is the best place in Louisville to see amazing Halloween light displays, complete with graveyards, interactive displays, and – last time I was there – a zombified Selfie Booth. A walk down Halloween on Hillcrest in October after dark is guaranteed to get you in the Halloween spirit!
If you’re lucky, maybe you’ll be able to witness a fight between 2 dads who have been competing for years for the best Halloween lawn display. Gosh, darn-it Brian, Steve has just about HAD IT with your strobe light BS.
- Halloween on Hillcrest | Address: Hillcrest Avenue & Frankfort Avenue, Louisville, KY
At the Halloween Lights Drive Through in Fort Boonesborough State Park in Richmond, KY, you can enjoy the sights, sounds and scares of over one and one-half miles of Halloween lights and displays from the comfort of your car! We can’t guarantee there will be any Dads fighting, though.
- Halloween Lights Drive Through | Address: 4375 Boonesboro Rd.Richmond, KY 40475
Go on a Spooky Ghost Tour
Take a haunted tour of Newport Kentucky to hear tales of murder, suicide and even decapitation (oooh!). You’ll learn the horrifying story of Bobby Mackey’s wicked haunting, and discover the details of some of Newport’s most infamous unsolved crimes!
- Newport Haunted Ghost Tour | Book Tickets Online
Ghost tour, meet cocktail & food tour! Venture out with Louisville Food Tours after dark and explore the hidden stories of Louisville’s haunted past. As you eat and drink your way down Whiskey Row, you’ll meet the resident ghosts of Louisville’s historic downtown, trace the footsteps of bourbon magnates and mobsters, see Al Capone’s secret getaway, discover hidden speakeasies in the belly of Whiskey Row, and learn the shocking truth about Prohibition.
- Phantoms of Prohibition Cocktails & Bites Tour | Book Tickets Online
Old Louisville is one of the most beautiful neighborhoods of Louisville (actually, it’s my favorite neighborhood in all of Louisville. Sorry other neighborhoods, I love you too, but Old Louisville is bae).
The streets are lined with massive old trees and the largest collection of historical Victorian homes in the world. A walk through this historic neighborhood in autumn is the best way to fully absorb the fall colors and see some truly incredible Halloween lawn displays.
As you explore blocks of gorgeous, mansion-esque Victorian homes, you can uncover the chilling stories of their former inhabitants: bourbon barons, racetrack royalty, and tobacco titans in the booming 1800s. That’s right, Old Louisville is one of the most haunted places in Louisville! You can get all of the spine-tingling details on the Old Louisville Ghost Tour.
For a complete list of ghost tours throughout Kentucky, head over to this guide on Funtober.
Get Scared at a Haunted House
There are a huge amount of Haunted Houses in Louisville annually, a fact that is directly tied to the thriving local theater scene. Actors love a chance to douse themselves in fake blood and chase after terrified guests (usually me) while wielding chainsaws. So if you want some really convincingly scary Haunted Houses, Louisville is the spot – but prepare to be terrified.
As if visiting Haunted Houses weren’t fun enough, Louisville took it up a notch: the Danger Run Haunted House Scavenger Hunt combines the thrill of solving cryptic clues in the car with your friends or family while getting lost in creepy corners and visiting multiple Haunted Houses in Louisville (if you can find them!) – all in one fun packed night!
But there are even more Haunted Houses all over Kentucky! Fright Nights near Lexington is so scary I literally can’t even look at the web page (I think something might be coming through my computer to get me???). All I can tell you is that you’ll be wandering through twisted corridors to uncover the dark secrets of Doctor Doom’s laboratory… yikes!
If you make it out alive, will you let me know how it is? I’m way too scared to go myself.
- Fright Nights | Address: 4001 Athens-Boonesboro Road, Lexington, Kentucky
Black Orchard Haunt in Shelbyville, Kentucky revolves around a demented story about a backwoods slaughterhouse, cannibalism, and religious zealots. Which, honestly, ticks all of my boxes. Fun!
Here’s the sitch: Brothers Stitch and Theodore Black now have control of the family business Black Orchard Meats. They bring a message from their savior The Vultures: the meat is still rancid and doesn’t taste quite right. Step inside and see if you can figure out WHAT’S IN THE BARN! (Care to take a guess?)
This haunt is guaranteed to turn anyone’s stomach and leave them grossed out – Black Orchard Haunt is definitely the place to go if horrific gore is for you.
- Black Orchard Haunt | Address: 704 Kentucky St, Shelbyville, KY 40065
You can browse Kentucky haunted houses by region, event type, and even level of scariness (phew) on the Kentucky Haunted Houses website.
Tour the Waverly Hills Sanatorium
If you’ve ever watched a TV show about the most haunted places in the world, then you’ve probably heard of the Waverly Hills Sanatorium – it’s featured on just about all of them. In the early 1900s, Louisville was ravaged by an outbreak of tuberculosis, known as the “White Plague,” and the Sanatorium was built to house the sick and dying.
Louisville’s old tuberculosis Sanatorium was filled to the brim during the first half of the 1900s. There were so many dead that the Sanatorium built an infamous body chute to send the deceased directly down the hill to the crematorium. Creepy!
Later on, the building became a prison, had a brief stint as the proposed site of the world’s largest statue of Jesus (plans fell through), and finally, came to rest in peace as a haunted attraction.
Today, the building itself is spooky enough to give anyone chills. But during the Halloween season, Waverly Hills turns itself into a thrilling Haunted House. There are said to be several ghosts still haunting the echoing halls. Ahhh!
- Waverly Hills Sanatorium | Address: 8501 Standing Oak Dr., Louisville, Ky
Psst: We’ve got a whole guide full of tons more things to do in the fall in Louisville!
Bourbon Tasting on The Kentucky Bourbon Trail
Bourbon is Kentucky’s proudest creation. Sure, it’s legally possible to create bourbon outside of Kentucky, but I’ve never had anything that compares (so you guys might as well just stop trying).
The secret behind Kentucky bourbon is the sweet limestone-filtered water which flows naturally through the state. Bourbon distilleries that rely on this sweet natural water source are sprinkled throughout central Kentucky, and the drive to see them is always absolutely gorgeous – but especially so in the fall.
An inexpensive visit to a bourbon distillery typically includes an informative tour of the distillery and a tasting of several types of bourbon, sometimes paired with chocolate bourbon balls!
Our favorite bourbon distilleries to visit in the fall are Woodford Reserve and Maker’s Mark. On your way to each distillery, you’ll drive past picturesque horse farms, rolling hills, and beautiful forests of brightly colored fall foliage.
Visiting Bourbon Distilleries is the best way to see the beautiful countryside of Kentucky! Fall in Kentucky doesn’t get better than this, y’all. We’ve even created the perfect Kentucky Bourbon Trail Itinerary to make a weekend of it!
We recommend booking a tour with a Louisville-based tour company that will take care of the planning (and most importantly, the driving) for you. This tour visits 3 bourbon distilleries of your choice.
- Maker’s Mark Distillery | Address: 3350 Burks Spring Road, Loretto, KY
- Woodford Reserve Distillery | Address: 7855 McCracken Pike, Versailles, KY
Watch Horse Races at Fall Meets
Everyone knows that Louisville is the home of the Kentucky Derby, the world’s most famous horse race. But the Derby is in May, and this is a list of things to do in the fall in Kentucky… so, what?
Well, let me introduce you to the magic of Fall Meets, which have all of the excitement and none of the tourists!
You can enjoy Mint Juleps, the thunder of hooves, the roaring crowd, and the fanciest hats you’ll ever see throughout the fall at Churchill Down’s Fall Meets. Churchill Downs hosts fall races all season long: check the Churchill Downs Calendar for full details.
- Churchill Downs | Address: 700 Central Ave, Louisville, KY
Head to Lexington’s Keeneland Race Course, widely considered by everyone (except, perhaps, Louisville residents, who are biased) to be the most beautiful racetrack in the world!
Wear something tweed and, if it’s especially crisp, order a cup of Burgoo, a very Kentucky stew that definitely used to have questionable ingredients in it but doesn’t anymore (probably) and is delicious (usually).
The Fall Meet schedule is usually posted by the end of August – check the site for specific dates and details!
- Keeneland | Address: 4201 Versailles Road, Lexington, KY
Experience Louisville’s Jack O’Lantern Spectacular
Louisville’s Jack O’Lantern Spectacular in Iroquois Park is hands down the most incredible and unique Halloween event in Kentucky – do NOT miss it! The walking path through the park comes alive with over 5,000 artist-carved pumpkins and illuminated themed scenes.
I can’t tell you how incredibly magical it is to take a glittering candle-lit walk through thousands of impeccably carved pumpkins, all built together to form larger-than-life works of art. It’s the most special Halloween event in Louisville!
For folks with sensory processing challenges, there is a special Autism-friendly night without music or special effects – just flickering pumpkins and quiet.
The show runs daily throughout October from dusk to 10pm on weekdays (Sunday-Thursday), and until 11pm on Friday & Saturday. I suggest arriving either very early or very late to beat the lines – an hour before closing is usually quieter. For more tips, check out our insider guide to the Louisville Jack O Lantern Spectacular.
As a bonus, your ticket purchase directly supports the non-profit Parks Alliance of Louisville and the community-driven projects they support in Louisville’s public parks and community centers.
- Jack O’Lantern Spectacular | Address: Iroquois Park, 1080 Amphitheater Rd, Louisville KY
Get Lost in a Corn Maze
Devine’s Corn Maze and Pumpkin Patch in Harrodsburg, Kentucky (not too far from Lexington) has it all: a giant corn maze, zip lines, pumpkin picking, marshmallow roasting, and plenty of fun and games for little ones of all ages! It’s great family fun.
At least, until Halloween weekend, when things get real freakin’ spooky.
On Halloween weekend, you’ll get lost in the dark amidst the rustling corn as your nightmares come alive – keep an eye out for Children of the Corn, Jason, Freddy, Pin Head, Saw, Exorcist, and more. Ahhh!
- Devine’s Corn Maze and Pumpkin Patch | Address: 623 Talmage-Mayo Road, Harrodsburg, KY
Field of Screams in Brandenburg is Kentuckiana’s largest haunted attraction and first haunted corn maze. Scare yourself silly by trying to find your way out of a six-acre cornfield maze, taking a hellish haunted hayride through a monster-infested terrain, or fighting your way through a laser tag horror scape!
- Field of Screams | Address: 248 Darnall Ave, Brandenburg, KY
Corn mazes are fun enough on their own, but for extremely competitive game-lovers like my husband, there is one thing that would make the entire experience WAY more fun, and that’s a murder mystery corn maze.
Welcome to Trunnel’s Farm Market‘s “Farm Scene Investigation.” Here’s the sitch: Farmer Joe is missing. There was an accident, and it appears to be foul play (get it?). There are seven farm animal suspects for you to investigate. You’ll need to find six location scenes to collect all the evidence and find the weapon, the suspect, and location where the crime took place. If you can solve the mystery, you’ll put the guilty farm animal behind bars, save farmer Joe, and win a prize!
After you’re done living your best Agatha Christie life, you can pick a pumpkin, ride a wagon, pet some animals, ride a swing or slide, play “hillbilly golf” whatever that is, race ducks, pan for gold, fire apples out of slingshots, bathe in a tub of corn kernels, jump on giant hay bales, and/or have a bonfire. So, pretty much anything your heart desires, really. Is this … what heaven is like??
- Trunnel’s Farm Market | Address: 9255 U.S. Highway 431, Utica, Kentucky
For a complete list of corn mazes in Kentucky, head over to Funtober.
Do you love fall in Kentucky as much as we do? Are we missing your favorite fall activity? Leave us a comment below!
Oh, and one last thing: our feature image is of the scenic Iron Bridge near Bowling Green, Kentucky. It isn’t technically a fall activity, but it is pretty freakin’ gorgeous in the fall. Isn’t fall in Kentucky beautiful, y’all?
Psst: We have a few other posts to help you make the most of fall in Louisville and the rest of Kentucky. Check them out:
- 35 Epic Pumpkin Patches in Kentucky to Visit This Fall
- 14 Things to Do to Celebrate Fall in Louisville, Kentucky
- Louisville Jack-O-Lantern Spectacular Visitor’s Guide (& Insider Tips)
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