14 days in Kentucky Itinerary

14 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

Make it your trip
Drive
1
Middlesboro
— 1 night
Drive
2
Cave City
— 2 nights
Drive
3
Louisville
— 5 nights
Drive
4
Lexington
— 5 nights
Drive

S M T W T F S
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Middlesboro

— 1 night
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. On the 14th (Sun), explore the wealth of natural beauty at Cumberland Gap National Historical Park. On the 15th (Mon), you'll have a packed day of sightseeing: admire the majestic nature at Levi Jackson Wilderness Road Park, then take an in-depth tour of Harland Sanders Cafe and Museum, and then stroll around Sanders Park.

To see where to stay, ratings, more things to do, and more tourist information, you can read our Middlesboro visit planning website.

Knoxville to Middlesboro is an approximately 1.5-hour car ride. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In October, plan for daily highs up to 71°F, and evening lows to 47°F. Finish up your sightseeing early on the 15th (Mon) so you can travel to Cave City.

Things to do in Middlesboro

Parks · Nature · Museums

Side Trips

Cave City

— 2 nights
Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
On the 16th (Tue), see the interesting displays at Mammoth Cave Wildlife Museum, examine the collection at Dinosaur World, and then Head underground at Hidden River Cave and American Cave Museum. On your second day here, explore the fascinating underground world of Diamond Caverns, take an in-depth tour of Historic RailPark & Train Museum, then join the crowd at NCM Motorsports Park, and finally explore the fascinating underground world of Onyx Cave.

For reviews, ratings, photos, and tourist information, you can read our Cave City travel route planner.

You can drive from Middlesboro to Cave City in 3.5 hours. In October in Cave City, expect temperatures between 71°F during the day and 48°F at night. Finish up your sightseeing early on the 17th (Wed) so you can go by car to Louisville.

Things to do in Cave City

Parks · Nature · Museums

Side Trips

Louisville

— 5 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Conrad-Caldwell House Museum (Conrad's Castle) and Historic Locust Grove will appeal to history buffs. You'll discover tucked-away gems like The Abbey of Gethsemani and Kentucky Peerless Distilling Co. Change things up with these side-trips from Louisville: Elizabethtown (Brown-Pusey House & Swope's Cars of Yesteryear Museum) and Bardstown (Old Bardstown Village Civil War Museum, My Old Kentucky Home, &more). There's much more to do: walk around The Parklands of Floyds Fork, sample the fine beverages at Kentucky Artisan Distillery, explore the world behind art at 21c Museum Hotel, and engage your brain at Kentucky Science Center.

To find reviews, other places to visit, and other tourist information, read our Louisville trip builder.

Getting from Cave City to Louisville by car takes about 1.5 hours. Other options: do a combination of car and bus; or do a combination of taxi and bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect a daytime high around 71°F in October, and nighttime lows around 50°F. Cap off your sightseeing on the 22nd (Mon) early enough to go by car to Lexington.

Things to do in Louisville

Museums · Historic Sites · Parks · Breweries & Distilleries

Side Trips

Lexington

— 5 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 explore and learn at Ashland: The Henry Clay Estate and The Great American Dollhouse Museum. Deepen your sense of the past at sights like Lexington Cemetery and Waveland State Historic Site. Venture out of the city with trips to Kentucky Vietnam Veterans Memorial (in Frankfort), Kentucky Artisan Center at Berea (in Berea) and Red River Gorge Geological Area (in Winchester). There's lots more to do: take in the history at Perryville Battlefield State Historic Site, see the interesting displays at Aviation Museum of Kentucky, walk around The Arboretum, and sample the tasty concoctions at West Sixth Brewing.

For traveler tips, photos, where to stay, and more tourist information, read Lexington online attractions planner.

Getting from Louisville to Lexington by car takes about 1.5 hours. Other options: take a bus. October in Lexington sees daily highs of 70°F and lows of 49°F at night. Cap off your sightseeing on the 27th (Sat) early enough to go by car back home.

Things to do in Lexington

Historic Sites · Parks · Museums · Shopping

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.