The town skyline of Frankfort, Kentucky, at dusk, with the Kentucky River winding through the scene.

2024's Towns In Kentucky That Come Alive In The Fall

Are you looking to enjoy a fall getaway in Kentucky? Join us as we cover some of the best towns in 2024 to visit during your trip. We will cover a variety of things to see and do while in and around these communities, including the best parks to see colorful autumn foliage, seasonal events, and other locales that are totally worth checking out during your stay.

From Kentucky's densely forested eastern half in the Appalachian Mountains to Lousiville, there are fall gems in the Bluegrass State regardless of where you decide to go.

Bardstown

Autumn colors bring vibrancy to a state park in Bardstown, Kentucky.
Autumn colors bring vibrancy to a state park in Bardstown, Kentucky.

Bardstown, Kentucky, sees its fall peak foliage from mid-October to early November. The town’s rolling hills and surrounding forests in its central portion of the state make for a perfect place to peep autumn colors in 2024.

My Old Kentucky Home State Park, which hugs the southern side of town, is perhaps the easiest and most accessible spot to go for a walk through the local woodlands. On the other hand, Bluegrass Parkway provides a picturesque drive with sweeping views of the countryside.

Although Bardstown’s earlier festivals have passed, the area still offers the ongoing Jack O'Lantern Spectacular at nearby Louisville’s Iroquois Park, running through November 2, and the Bardstown Arts and Crafts Festival, where visitors can enjoy local crafts, live music, and handcrafted products. If you do not make it to the Bourbon Festival, have no worries, as distilleries like the Willett Distillery and Heaven Hill Bourbon Experience are open year-round and perfectly complement any chilly fall day.

Midway

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

Midway is a hidden gem for fall travelers in the heart of Kentucky’s horse country; this small town of fewer than 1,800 residents is perfect for anyone looking to escape the hustle and bustle of big city life.

For leaf-peepers, the nearby Kentucky River is an idyllic spot, with trails offering views of the water and abundant trees lining its banks. Closer is the South Elkhorn Creek, which meanders just north of town. It makes for a scenic backdrop to several farm and equestrian facilities, including Kismet Thoroughbred Farms, making this town one of the best spots to go for horse enthusiasts this fall.

Midway brings more than just parks and horse farms. Visitors in late October can enjoy nearby events like the Just Piddlin Farm Tours in Woodford County, which features a corn maze, pumpkin patch, and hayrides, open through November 2. It’s a great way to enjoy the autumn atmosphere while taking in the fall colors around the region

Pineville

Powderhorn Arch in Pine Mountain State Resort Park, Pineville, Kentucky
Powderhorn Arch in Pine Mountain State Resort Park, Pineville, KY. Editorial credit: Michele Korfhage / Shutterstock.com

In the Appalachian Mountains is the town of Pineville, an amazing spot for outdoor enthusiasts in Kentucky to visit this fall. Pine Mountain and the Cumberland River, two of the most notable natural features nearby, both offer breathtaking views of vibrant trees that begin to turn colorful from early October to November.

Visitors can enjoy the fall colors by hiking the Pine Mountain State Resort Park’s trails, where overlooks like Chained Rock provide a lookout point over the town and the heavily forested valley below. The nearby Cumberland Gap National Historical Park also features excellent leaf-peeping spots with panoramic views from Pinnacle Overlook, where the borders of Kentucky, Virginia, and Tennessee meet.

It is also a good idea to explore the town’s riverside parks or take scenic drives along mountain roads to experience the full splendor of the fall season in this very rural portion of the state.

Harrodsburg

Three adult riders follow a scenic trail toward a historic barn at Shaker Village of Pleasant Hill in Harrodsburg, Kentucky
A historic barn at Shaker Village of Pleasant Hill in Harrodsburg, Kentucky.

Just south of Lexington is Harrodsburg, Kentucky’s oldest town and, furthermore, the first permanent American settlement that is west of the Appalachians. The town’s location near Herrington Lake and the Kentucky River makes it a great place to visit in both the summer and fall months.

Shaker Village of Pleasant Hill is a popular resort nearby that doubles as a spot for leaf-peeping in October and November. Here, visitors can explore miles of hiking trails through maintained woodlands and meadows. The historic village itself, with its preserved 19th-century architecture, is even more picturesque at this vibrant time of the year.

In the center of Harrodsburg is Old Fort Harrod State Park, another historic park that is both educational and scenic. It is filled with period-accurate structures representing life here in the 18th century, and in late October, a haunted house set near the park's cemetery, the oldest in the state! A perfect stop to check out before Halloween.

Paducah

Historic buildings in the downtown district of Paducah, Kentucky
The downtown district of Paducah, Kentucky. Editorial credit: Angela N Perryman / Shutterstock.com

At the confluence of the Ohio and Tennessee Rivers at the far northern reach of the state, Paducah is best known for its historic riverside parks, artistic scene, and intriguing locales like The National Quilt Museum.

The nearby Land Between the Lakes National Recreation Area is an excellent destination for seeing the fall colors of the region, with miles of trails winding through its rich forests. Paducah’s fall season is also marked by the Downtown Fall Festival, featuring craft tables, food vendors, and live music that bring the streets to life.

Staying in town for the night? Definitely consider booking a room at The 1857 Hotel- set in a gorgeous red brick building that is just a few minutes walk from the riverfront and the historic district of downtown Paducah.

Frankfort

The Kentucky River meanders gracefully around the downtown urban core of Frankfort, Kentucky
The Kentucky River near downtown Frankfort, Kentucky.

We will finish off this list with the capital of Kentucky. Seated along the Kentucky River, Frankfurt is a gorgeous city of around 30,000 residents that, along with having many modern amenities, still maintains a small-town feel.

For a scenic view of the fall colors nearby, you can embark on a hike through Cove Spring Park, where its trails will take you through its colorful forests and to viewpoints of the waterfalls in the meandering streams throughout. The nearby Kentucky River also offers picturesque riverside walks. The historic grounds of the State Capitol building also make for a beautiful autumn stroll.

Frankfort’s annual Capital City Fall Festival brings the season to life with live music, local vendors, and seasonal foods. Visitors can also enjoy a couple of stops along Visitors can also enjoy a couple of stops along the Bourbon Trail here in Frankfort, with Buffalo Trace Distillery on Great Buffalo Trace and J. Mattingly 1845 Distillery located nearby at 20 Reilly Road.

Experience the Magic of Kentucky’s Fall Towns

Whether you've set out to taste the best bourbons in the world or want to shoot some landscape photography in the state's finest woodlands as the colors turn, Kentucky is a prime destination to explore this fall. There are a variety of must-visit towns in Kentucky, from the capital to tiny communities in the Appalachians, that appeal to anyone who wants to take an unforgettable road trip in the Bluegrass state. How many of these destinations will you explore before winter arrives in 2024?

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