4 days in Kentucky Itinerary

4 days in Kentucky Itinerary

Created using Inspirock Kentucky itinerary planner

©
Make it your trip
Drive
1
Lexington
— 2 nights
Drive
2
Middlesboro
— 1 night
Drive

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Lexington

— 2 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.
You'll discover tucked-away gems like Unique Horse Farm Tours and Distillery Tours. Venture out of the city with trips to Slade (Natural Bridge State Resort Park & Kentucky Reptile Zoo) and Red River Gorge Geological Area (in Winchester). The adventure continues: take in the pleasant sights at Kentucky Bourbon Trail, sample the fine beverages at Bluegrass Distillers, make a trip to Mary Todd Lincoln House, and sample the tasty concoctions at Lexington Brewing & Distilling Co..

To see traveler tips, ratings, more things to do, and more tourist information, you can read our Lexington driving holiday planner.

Roanoke to Lexington is an approximately 6.5-hour car ride. You can also fly; or take a bus. In November, daily temperatures in Lexington can reach 56°F, while at night they dip to 36°F. Wrap up your sightseeing on the 21st (Sat) to allow time to travel to Middlesboro.

Things to do in Lexington

Tours · Breweries & Distilleries · Parks · Outdoors

Side Trips

Middlesboro

— 1 night
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Kick off your visit on the 22nd (Sun): explore the striking landscape of Cumberland Gap National Historical Park.

To find photos, where to stay, ratings, and tourist information, use the Middlesboro driving holiday website.

You can drive from Lexington to Middlesboro in 2.5 hours. The time zone difference when traveling from Lexington to Middlesboro is minus 1 hour. In November in Middlesboro, expect temperatures between 58°F during the day and 34°F at night. Finish your sightseeing early on the 22nd (Sun) so you can travel back home.

Things to do in Middlesboro

Nature · Parks
Highlights from your trip

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.