16 days in Kentucky Itinerary

16 days in Kentucky Itinerary

Created using Inspirock Kentucky travel route builder

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Route & dates

16 days in Kentucky Itinerary

Start: Houston
Fly + Drive:  6​h 45​min
1
Paducah
— 2 nights
Drive:  2​h 30​min
2
Bowling Green
— 2 nights
Drive:  2​h
3
Louisville
— 4 nights
Drive:  1​h 45​min
4
Newport
— 1 night
Bus:  1​h 30​min
5
Lexington
— 4 nights
Drive:  2​h 30​min
6
Middlesboro
— 2 nights
Drive + Fly:  8​h 45​min
End: Houston

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 (Mon): take a leisurely stroll along Paducah Riverwalk. On the next day, steep yourself in history at William Clark Market House Museum, then explore the world behind art at The National Quilt Museum, then take an in-depth tour of Lloyd Tilghman House and Civil War Museum, and finally learn about winemaking at Purple Toad Winery.

For other places to visit, traveler tips, and tourist information, read our Paducah online route builder .

Houston to Paducah is an approximately 7-hour combination of flight and car. You can also do a combination of flight and bus; or drive. Prepare for little chillier weather when traveling from Houston in June: high temperatures in Paducah hover around 87°F and lows are around 67°F. Finish your sightseeing early on the 19th (Wed) so you can drive to Bowling Green.

Things to do in Paducah

Museums Historic Sites Wineries

Side Trip

Hopkinsville
Highlights from your plan
Purple Toad Winery ©
Purple Toad Winery
River Discovery Center ©
River Discovery Center
Casey Jones Distillery ©
Casey Jones Distillery

2
nights
Bowling Green

Bowling Green ©
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. On the 20th (Thu), take an in-depth tour of The Kentucky Museum, take in the spiritual surroundings of St. Joseph Catholic Church, stop by Jackson's Orchard, then examine the collection at National Corvette Museum, and finally join the crowd at NCM Motorsports Park. On the 21st (Fri), you'll have a packed day of sightseeing: get engrossed in the history at South Union Shaker Village, contemplate the long history of Riverview at Hobson Grove, then steep yourself in history at Bill Monroe's Home Place, and finally make a trip to 1921 Standard Oil Station.

For reviews, where to stay, more things to do, and more tourist information, use the Bowling Green day trip planning app .

Traveling by car from Paducah to Bowling Green takes 2.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 87°F, and evening lows to 66°F. Wrap up your sightseeing on the 21st (Fri) to allow time to drive to Louisville.

Things to do in Bowling Green

Museums Historic Sites Shopping

Side Trips

South Union Shaker Village, Bill Monroe's Home Place
Highlights from your plan
National Corvette Museum ©
National Corvette Museum
Bill Monroe's Home Place ©
Bill Monroe's Home Place
South Union Shaker Village ©
South Union Shaker Village

4
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Discover out-of-the-way places like Conrad-Caldwell House Museum (Conrad's Castle) and Historic Locust Grove. Louisville Slugger Museum & Factory and Virgil I. Gus Grissom Memorial Museum will appeal to museum buffs. Get out of town with these interesting Louisville side-trips: Swope's Cars of Yesteryear Museum (in Elizabethtown), Lanier Mansion State Historic Site (in Madison) and The Abbey of Gethsemani (in Trappist). There's still lots to do: explore the fascinating underground world of Louisville Mega Cavern, see the interesting displays at Kentucky Derby Museum, wander the streets of Old Louisville, and contemplate the long history of Spring Mill State Park.

For photos, other places to visit, ratings, and tourist information, go to the Louisville trip planner.

Drive from Bowling Green to Louisville in 2 hours. Alternatively, you can take a bus; or take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In June, plan for daily highs up to 86°F, and evening lows to 67°F. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Newport.

Things to do in Louisville

Historic Sites Museums Nature

Side Trips

Mitchell, Swope's Cars of Yesteryear Museum, Lanier Mansion State Historic Site, The Abbey of Gethsemani
Highlights from your plan
Swope's Cars of Yesteryear Museum ©
Swope's Cars of Yesteryear Museum
The Abbey of Gethsemani ©
The Abbey of Gethsemani

1
night
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. Start off your visit on the 26th (Wed): see the interesting displays at Creation Museum, contemplate in the serene atmosphere at Cathedral Basilica of the Assumption, then examine the collection at Lucky Cat Museum, and finally snap pictures at Newport Southbank Bridge a.k.a. Purple People Bridge.

For more things to do, ratings, where to stay, and other tourist information, read Newport trip itinerary planning website .

Drive from Louisville to Newport in 2 hours. Alternatively, you can take a bus. Traveling from Louisville in June, plan for little chillier nights in Newport, with lows around 61°F. Finish up your sightseeing early on the 26th (Wed) so you can catch the bus to Lexington.

Things to do in Newport

Museums Historic Sites

Side Trips

Cincinnati, Creation Museum
Highlights from your plan
Creation Museum
Creation Museum
Cathedral Basilica of the Assumption ©
Lucky Cat Museum ©
Lucky Cat Museum

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.
Popular historic sites such as Ashland: The Henry Clay Estate and Perryville Battlefield State Historic Site are in your itinerary. Eschew the tourist crowds and head to Kentucky Artisan Center at Berea and The Great American Dollhouse Museum. Change things up with these side-trips from Lexington: Harrodsburg (Old Fort Harrod State Park & Devine's Corn Maze & Pumpkin Patch), Rising Sons Home Farm Winery (in Lawrenceburg) and Four Roses Bourbon - Warehouse and Bottling Facility (in Coxs Creek). And it doesn't end there: see the interesting displays at Aviation Museum of Kentucky, sample the fine beverages at Bluegrass Distillers, try to win big at Keeneland, and explore the different monuments and memorials at Lexington Cemetery.

To see maps, other places to visit, ratings, and more tourist information, you can read our Lexington online day trip planner .

You can take a bus from Newport to Lexington in 1.5 hours. Alternatively, you can drive. In June, plan for daily highs up to 84°F, and evening lows to 64°F. Finish your sightseeing early on the 30th (Sun) to allow enough time to travel to Middlesboro.

Things to do in Lexington

Historic Sites Museums Fun & Games

Side Trips

Harrodsburg, Rising Sons Home Farm Winery, Perryville Battlefield State Historic Site, Four Roses Bourbon - Warehouse and Bottling Facility, Kentucky Vietnam Veterans Memorial
Highlights from your plan
Ashland: The Henry Clay Estate ©
Ashland: The Henry Clay Estate
The Great American Dollhouse Museum ©

2
nights
Middlesboro

Middlesboro ©
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Your day-by-day itinerary now includes Bell County Historical Society. Start off your visit on the 1st (Mon): examine the collection at Bell County Historical Society, get engrossed in the history at Abraham Lincoln Library and Museum, then see the interesting displays at Little Congress Bicycle Museum, then steep yourself in history at Dr. Thomas Walker State Historic Site, and finally take in the history at Camp Wildcat Battlefield.

Discover how to plan a Middlesboro trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Lexington to Middlesboro takes 2.5 hours. Traveling from Lexington to Middlesboro, you'll gain 1 hour due to the time zone difference. In June, plan for daily highs up to 84°F, and evening lows to 62°F. Wrap up your sightseeing by early afternoon on the 2nd (Tue) to allow time for travel back home.

Things to do in Middlesboro

Museums Historic Sites Wineries

Side Trips

Abraham Lincoln Library and Museum, Dr. Thomas Walker State Historic Site, Little Congress Bicycle Museum, Camp Wildcat Battlefield, Spout Spring Estates Winery and Vineyard
Highlights from your plan
Abraham Lincoln Library and Museum ©
Little Congress Bicycle Museum ©
Little Congress Bicycle Museum

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