39 days in Kentucky Itinerary

39 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

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Route & dates

39 days in Kentucky Itinerary

Start: New York City
Fly:  4​h 15​min
1
Lexington
— 9 nights
Drive:  2​h 30​min
2
Corbin
— 3 nights
Drive:  3​h 30​min
3
Mammoth Cave National Park
— 4 nights
Drive:  3​h 15​min
4
Paducah
— 6 nights
Drive:  3​h 45​min
5
Louisville
— 12 nights
Drive:  1​h 45​min
6
Newport
— 4 nights
Fly:  5​h
End: New York City

9
nights
Lexington

Lexington ©
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Get outdoors at Kentucky Horse Park and Natural Bridge State Resort Park. You'll find plenty of places to visit near Lexington: Ark Encounter (in Williamstown), Frankfort (Buffalo Trace Distillery, Old State Capitol, & more) and Claiborne Farm (in Paris). The adventure continues: catch the contagious excitement of Keeneland, take in the dramatic natural features at Lower Howard's Creek Nature and Heritage Preserve, examine the collection at The Great American Dollhouse Museum, and admire all the interesting features of Old Friends at Dream Chase Farm.

To find maps, photos, traveler tips, and tourist information, you can read our Lexington online day trip planner .

New York City to Lexington is an approximately 4.5-hour flight. You can also do a combination of bus and flight; or drive. When traveling from New York City in April, plan for a bit warmer days and about the same nights in Lexington: temperatures range from 68°F by day to 46°F at night. Cap off your sightseeing on the 2nd (Thu) early enough to travel to Corbin.

Things to do in Lexington

Parks Museums Trails

Side Trips

Frankfort, Slade, Danville, Versailles, Wild Turkey Distillery
Highlights from your plan
Kentucky Horse Park ©
Kentucky Horse Park
Natural Bridge State Resort Park ©
Natural Bridge State Resort Park
Salato Wildlife Education Center ©

3
nights
Corbin

Corbin ©
Corbin is a home rule-class city in Whitley and Knox counties in the southeastern portion of the U.S. Take a break from the city and head to Cumberland Falls State Resort Park and Mill Springs Mill. Explore Corbin's surroundings by going to Daniel Boone National Forest (in Winchester), Cumberland Gap National Historical Park (in Middlesboro) and Yahoo Falls (in Whitley City).

To find traveler tips, ratings, other places to visit, and more tourist information, read our Corbin trip itinerary planner.

Traveling by car from Lexington to Corbin takes 2 hours. Expect a daytime high around 76°F in May, and nighttime lows around 54°F. Finish your sightseeing early on the 5th (Sun) so you can travel to Mammoth Cave National Park.

Things to do in Corbin

Parks Nature Outdoors

Side Trips

Mill Springs Mill, Cumberland Gap National Historical Park, Yahoo Falls, Daniel Boone National Forest
Highlights from your plan
Cumberland Falls State Resort Park ©
Yahoo Falls ©
Yahoo Falls

4
nights
Mammoth Cave National Park

Mammoth Cave National Park ©
Mammoth Caves National Park is the longest cave system in the world so far discovered.
Get outdoors at Mammoth Cave National Park and Green River. The adventure continues: trek along Cedar Sink Trail, contemplate the waterfront views at Echo River, explore the fascinating underground world of Diamond Caverns, and stroll through Fat Man's Misery.

For more things to do, maps, reviews, and other tourist information, read our Mammoth Cave National Park road trip planner .

Getting from Corbin to Mammoth Cave National Park by car takes about 2.5 hours. You'll gain 1 hour traveling from Corbin to Mammoth Cave National Park due to the time zone difference. May in Mammoth Cave National Park sees daily highs of 76°F and lows of 56°F at night. Finish up your sightseeing early on the 9th (Thu) so you can go by car to Paducah.

Things to do in Mammoth Cave National Park

Parks Nature Outdoors

Side Trips

Horse Cave, Diamond Caverns
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
Fat Man's Misery ©
Fat Man's Misery
Cedar Sink Trail ©
Cedar Sink Trail

6
nights
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Get in touch with nature at Kenlake State Park and Columbus-Belmont State Park. Explore the numerous day-trip ideas around Paducah: Woodlands Nature Station (in Cadiz), Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium (in Golden Pond) and Kentucky Lake (in Gilbertsville). There's much more to do: admire the masterpieces at The National Quilt Museum, get in on the family fun at Maggie's Jungle Golf & Jungle Run, don't miss a visit to Floodwall Murals, and immerse yourself in nature at Pennyrile Forest State Resort Park.

For maps, more things to do, where to stay, and more tourist information, go to the Paducah trip website .

You can drive from Mammoth Cave National Park to Paducah in 3.5 hours. Alternatively, you can do a combination of taxi and bus. In May in Paducah, expect temperatures between 78°F during the day and 57°F at night. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to Louisville.

Things to do in Paducah

Parks Nature Wildlife

Side Trips

Gilbertsville, Columbus-Belmont State Park, Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium, Pennyrile Forest State Resort Park, Woodlands Nature Station
Highlights from your plan

12
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Visiting Louisville Mega Cavern and The Parklands of Floyds Fork will get you outdoors. Change things up with these side-trips from Louisville: Taylorsville (Taylorsville Lake State Park & Brashears Creek), Jefferson Memorial Forest (in Fairdale) and Bardstown (Willett Distilling Company & Barton 1792 Distillery). There's lots more to do: try your luck at Churchill Downs, snap pictures at The Big Four Bridge, test your problem-solving skills at popular escape rooms, and sample the fine beverages at Jim Beam American Stillhouse.

For ratings, more things to do, reviews, and more tourist information, use the Louisville road trip tool .

Traveling by car from Paducah to Louisville takes 4 hours. Alternatively, you can fly; or take a bus. Traveling from Paducah to Louisville, you'll lose 1 hour due to the time zone difference. In May, daytime highs in Louisville are 77°F, while nighttime lows are 58°F. Finish up your sightseeing early on the 27th (Mon) so you can go by car to Newport.

Things to do in Louisville

Parks Nature Wildlife

Side Trips

Taylorsville, Bardstown, Clermont, Jefferson Memorial Forest, Swope's Cars of Yesteryear Museum
Highlights from your plan
Louisville Slugger Museum & Factory ©
Jefferson Memorial Forest ©
Jefferson Memorial Forest
EP ©
EP "Tom" Sawyer State Park

4
nights
Newport

Newport ©
Newport is a home rule-class city at the confluence of the Ohio and Licking rivers in Campbell County, Kentucky, in the United States. Get out of town with these interesting Newport side-trips: EarthJOY Tree Adventures (in Germantown) and Maysville (EAT Gallery & Kentucky Gateway Museum Center). Next up on the itinerary: meet the residents at Newport Aquarium, indulge your thirst for a good beer at Braxton Brewing Company, get lost in a book at Kenton County Public Library, and enjoy some diversion at George Rogers Clark Park.

To find photos, more things to do, traveler tips, and tourist information, read our Newport tour planner.

You can drive from Louisville to Newport in 2 hours. Another option is to take a bus. Plan for little chillier nights when traveling from Louisville in May since evenings lows in Newport dip to 53°F. On the 31st (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Newport

Parks Museums Breweries & Distilleries

Side Trips

Covington, Maysville, Vent Haven Museum, EarthJOY Tree Adventures, Kenton County Public Library
Highlights from your plan
Newport Aquarium ©
Newport Aquarium
EarthJOY Tree Adventures ©
EarthJOY Tree Adventures
New Riff Distillery ©
New Riff Distillery

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