4 days in Kentucky Itinerary

4 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

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Make it your trip
Drive
1
Middlesboro
— 1 day
Drive
2
Lexington
— 3 nights
Drive

S M T W T F S
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Middlesboro

— 1 day
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. On the 19th (Thu), explore the wealth of natural beauty at Cumberland Gap National Historical Park.

To find traveler tips, photos, where to stay, and other tourist information, you can read our Middlesboro online tour itinerary planner.

Roanoke to Middlesboro is an approximately 4.5-hour car ride. You can also do a combination of flight and car. Traveling from Roanoke to Middlesboro, you'll gain 1 hour due to the time zone difference. Expect a daytime high around 58°F in November, and nighttime lows around 34°F. Finish up your sightseeing early on the 19th (Thu) so you can travel to Lexington.

Things to do in Middlesboro

Nature · Parks
Highlights from your trip

Lexington

— 3 nights

Horse Capital of the World

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Get in touch with nature at Unique Horse Farm Tours and Natural Bridge State Resort Park. You'll discover tucked-away gems like Distillery Tours and Red River Gorge Geological Area. Explore the numerous day-trip ideas around Lexington: Four Roses (in Lawrenceburg) and Four Roses Bourbon - Warehouse and Bottling Facility (in Coxs Creek). And it doesn't end there: go for a walk through Kentucky Bourbon Trail, sample the tasty concoctions at Lexington Brewing & Distilling Co., and steep yourself in history at Mary Todd Lincoln House.

For where to stay, traveler tips, more things to do, and more tourist information, read Lexington trip itinerary planner.

Traveling by car from Middlesboro to Lexington takes 2.5 hours. Traveling from Middlesboro to Lexington, you'll lose 1 hour due to the time zone difference. In November, daily temperatures in Lexington can reach 56°F, while at night they dip to 36°F. Cap off your sightseeing on the 22nd (Sun) early enough to go by car back home.

Things to do in Lexington

Breweries & Distilleries · Tours · Parks · Outdoors

Side Trips

Kentucky travel guide

4.5
Caves · Specialty Museums · Distilleries
The Bluegrass State
A diverse region of sprawling farmland and rich cultural heritage, Kentucky is the birthplace of American horse racing and home to the world-famous Kentucky Derby. While the cities of Lexington and Louisville experience the majority of the state's tourism, Kentucky is also a favorite among outdoor enthusiasts with its array of natural attractions, including the Cumberland Gap and the world's longest cave system at Mammoth Cave National Park. Take a tour through original Civil War battlefields to delve into the nation's history, or head to one of the many bourbon distilleries to learn more about Kentucky's most famous export.