14 days in Kentucky Itinerary

14 days in Kentucky Itinerary

Created using Inspirock Kentucky holiday planner

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Route & dates

14 days in Kentucky Itinerary

Start: Boston
Fly:  6​h
1
Lexington
— 4 nights
Drive:  1​h 30​min
2
Louisville
— 4 nights
Drive:  1​h 30​min
3
Park City
— 3 nights
Drive:  2​h 45​min
4
Paducah
— 2 nights
Fly:  6​h 30​min
End: Boston

4
nights
Lexington

Lexington
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Your inner history buff will appreciate Ashland: The Henry Clay Estate and Perryville Battlefield State Historic Site. Get a sense of the local culture at The Great American Dollhouse Museum and Lexington Cemetery. Explore Lexington's surroundings by going to Old Fort Harrod State Park (in Harrodsburg), Kentucky Artisan Center at Berea (in Berea) and Ark Encounter (in Williamstown). The adventure continues: explore the different monuments and memorials at Kentucky Vietnam Veterans Memorial, get a taste of the local shopping with Damselfly Gallery, immerse yourself in nature at Kentucky Horse Park, and brush up on your knowledge of spirits at Barrel House Distillery.

To find more things to do, ratings, maps, and other tourist information, you can read our Lexington attractions planner .

Boston to Lexington is an approximately 6-hour flight. You can also drive; or do a combination of train and bus. When traveling from Boston in October, plan for a bit warmer days and about the same nights in Lexington: temperatures range from 70°F by day to 49°F at night. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Louisville.

Things to do in Lexington

Museums Historic Sites Parks

Side Trips

Midway, Ark Encounter, Old Fort Harrod State Park, Perryville Battlefield State Historic Site, The Great American Dollhouse Museum
Highlights from your plan
Ark Encounter
Ark Encounter
The Great American Dollhouse Museum ©

4
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Get outdoors at Louisville Mega Cavern and My Old Kentucky Home. Do some cultural sightseeing at Conrad-Caldwell House Museum (Conrad's Castle) and Zachary Taylor National Cemetery. You'll find plenty of places to visit near Louisville: Old Bardstown Village Civil War Museum (in Bardstown) and Elizabethtown (Brown-Pusey House & Swope's Cars of Yesteryear Museum). There's lots more to do: contemplate the long history of Locust Grove, examine the collection at Louisville Slugger Museum & Factory, take a stroll through Old Louisville, and try your luck at Churchill Downs.

To find traveler tips, ratings, reviews, and other tourist information, use the Louisville trip itinerary tool .

You can drive from Lexington to Louisville in 1.5 hours. Alternatively, you can take a bus. In October in Louisville, expect temperatures between 71°F during the day and 50°F at night. Finish your sightseeing early on the 13th (Sun) so you can travel to Park City.

Things to do in Louisville

Museums Historic Sites Nature

Side Trips

Bardstown, Elizabethtown
Highlights from your plan
Historic Locust Grove ©
Historic Locust Grove
Swope's Cars of Yesteryear Museum ©
Swope's Cars of Yesteryear Museum

3
nights
Park City

Park City ©
Park City is a home rule-class city in Barren County, Kentucky, United States. Take a break from the city and head to Fat Man's Misery and Hidden River Cave and American Cave Museum. Your cultural itinerary includes sights like Historic RailPark and Train Museum and Aviation Heritage Park. Step out of Park City to go to Bowling Green and see National Corvette Museum, which is approximately 34 minutes away. It doesn't end there: explore the fascinating underground world of Diamond Caverns and examine the collection at Dinosaur World.

To see reviews, other places to visit, photos, and other tourist information, you can read our Park City itinerary planner.

Traveling by car from Louisville to Park City takes 1.5 hours. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In October, plan for daily highs up to 71°F, and evening lows to 48°F. Wrap up your sightseeing on the 16th (Wed) to allow time to travel to Paducah.

Things to do in Park City

Parks Nature Museums

Side Trips

Bowling Green, Mammoth Cave National Park, Cave City, Hidden River Cave and American Cave Museum
Highlights from your plan
Fat Man's Misery ©
Fat Man's Misery
Aviation Heritage Park ©
Aviation Heritage Park
Dinosaur World ©
Dinosaur World

2
nights
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Start off your visit on the 17th (Thu): take in the waterfront at Paducah Riverwalk, see human ingenuity at work at Kentucky Dam, and then identify plant and animal life at Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium. On the 18th (Fri), you'll have a packed day of sightseeing: see the interesting displays at Paducah Distilled Spirits, then examine the collection at River Discovery Center, and then do a tasting at Purple Toad Winery.

For reviews and more tourist information, refer to the Paducah trip maker .

Getting from Park City to Paducah by car takes about 3 hours. In October in Paducah, expect temperatures between 73°F during the day and 50°F at night. Wrap up your sightseeing on the 18th (Fri) early enough to travel back home.

Things to do in Paducah

Parks Wildlife Museums

Side Trip

Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium
Highlights from your plan
River Discovery Center ©
River Discovery Center
Purple Toad Winery ©
Purple Toad Winery

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