🍁 Ideal Fall Kentucky Road Trips

Crisp air, gold leaves, bourbon scents, and bluegrass views. Pick a loop, gas up, and go.

1) Red River Gorge & Natural Bridge Loop

Lexington → Slade → Sky Bridge → Nada Tunnel → Lexington (1–2 days)

• Must-do: Auxier Ridge hike, Chimney Top overlook, lift to Natural Bridge.
• Eat: Miguel’s Pizza; get a slice + Ale-8-One.
• Stay: A-frame cabins or treehouses around Slade.

Open in Google Maps →

2) Bourbon Trail Harvest Swing

Frankfort → Bardstown → Loretto → Louisville (2–3 days)

• Tours to book: Buffalo Trace, Maker’s Mark (Loretto), Heaven Hill (Bardstown).
• Stroll: Bardstown’s historic square—named “Most Beautiful Small Town in America.”
• Bite: Hot brown in Louisville on your way out.

Plan with the Bourbon Trail map →

3) Horse Country Sunday Drive

Lexington → Keeneland → Midway → Versailles (½–1 day)

• Catch: Fall meet at Keeneland (check race dates).
• Photo-ops: Stone fences & sunrise barns on Old Frankfort Pike.
• Midway: Quaint main street, antique stops, and porch-sit vibes.

Keeneland map →

4) Cumberland Falls & Daniel Boone Parkway

London → Cumberland Falls → Bee Rock → Laurel River Lake (1–2 days)

• Chase: The “Moonbow” at Cumberland Falls (check lunar calendar).
• Paddle: Calm coves at Laurel River Lake with peak foliage reflections.
• Hike: Short and sweet views at Bee Rock Overlook.

5) Mammoth Cave to Nolin Lake Loop

Park City → Mammoth Cave → Brownsville → Nolin Lake (1–2 days)

• Book ahead: Cave tours sell out in peak weeks.
• Scenic: Backroads along the Green River for leaf-peeping.
• Relax: Sunset at Nolin Lake before heading home.

6) Eastern KY Appalachia Ridge Run

Berea → Redbird Crest → Pine Mountain → Pikeville (2–3 days)

• Hike: Pine Mountain’s overlooks are next-level in October light.
• Culture: Folk art stops around Berea; makan’ beans & cornbread along the way.
• View: Pikeville Overlook for a proper finale.

Whether you’re leaf-peeping at Cumberland Falls, sipping your way down the Kentucky Bourbon Trail, or heading east into the Appalachian ridges, these are the best Kentucky fall road trips to take this season. Just don’t forget to pack the essentials: a Kentucky fall tee, a cozy sweatshirt, and a warm hat to handle the chill.

Gear up, hit the road, and tag us with your pics — because fall in Kentucky only comes once a year, and y’all need to make the most of it.

Road-Trip Pack List (KY for KY Edition)

• Layers: flannel + lightweight rain shell
• Comfy boots & wool socks
• Insulated mug + cooler
• Paper map for dead-zone hollers
• 🎒 Fresh fall tee & beanie/hat

Ready to roll?

Snag the gear, plan the loop, and tag us with your leaf-peep pics: #KYforKY.