Kentucky Road Trippin'
Narrow your options by:
Categories
Color
Size
🍁 Ideal Fall Kentucky Road Trips
Crisp air, gold leaves, bourbon scents, and bluegrass views. Pick a loop, gas up, and go.
Fall in Kentucky is pure magic — rolling hills painted in gold, crisp air through the hollers, and bourbon waiting at every pit stop. If you’ve been searching for the best Kentucky fall road trip ideas or wondering where to catch peak Kentucky fall foliage in 2025, we’ve mapped out the drives that locals swear by. From the iconic Red River Gorge to the bourbon-scented backroads of Bardstown, here’s your guide to the ultimate Kentucky fall drives — with a side of tees, sweats, and hats to keep you road-trip ready.
Best timing: Late Sept–early Nov (peak varies east→west). Pro tip: Book distillery tours ahead and keep a cooler for farm-stand finds.
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.
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.
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.
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.
Shop New Fall Styles Find Us In-Store