30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

Make it your trip
Drive
1
Louisville
— 7 nights
Drive
2
Paducah
— 5 nights
Drive
3
Hopkinsville
— 3 nights
Drive
4
Mammoth Cave National Park
— 3 nights
Drive
5
Lebanon
— 2 nights
Drive
6
Middlesboro
— 2 nights
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7
Lexington
— 7 nights
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Louisville

— 7 nights

Derby City

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 Cave Hill Cemetery. Change things up with these side-trips from Louisville: Bardstown (Old Bardstown Village Civil War Museum & Willett Distilling Company). The adventure continues: learn insider's secrets on a distillery tour, sample the fine beverages at Angel's Envy Distillery, get thoroughly spooked out with a ghost and vampire tour, and try to win big at Churchill Downs.

For photos, reviews, and other tourist information, read Louisville driving holiday app.

Columbus to Louisville is an approximately 3.5-hour car ride. You can also take a bus; or fly. In November, daytime highs in Louisville are 57°F, while nighttime lows are 37°F. Finish up your sightseeing early on the 8th (Mon) so you can go by car to Paducah.

Things to do in Louisville

Museums · Breweries & Distilleries · Historic Sites · Parks

Side Trip

Paducah

— 5 nights
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. You'll discover tucked-away gems like Purple Toad Winery and Kentucky Dam. Change things up with a short trip to Audubon State Park in Henderson (about 1h 45 min away). There's much more to do: take a leisurely stroll along Paducah Riverwalk, take an in-depth tour of Paducah Railroad Museum, stroll around Bob Noble Park, and admire the natural beauty at Apple Valley Hillbilly Garden and Toyland.

To find photos, other places to visit, where to stay, and tourist information, use the Paducah journey builder site.

You can drive from Louisville to Paducah in 4 hours. Other options are to fly; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In November, plan for daily highs up to 59°F, and evening lows to 37°F. Finish your sightseeing early on the 13th (Sat) to allow enough time to drive to Hopkinsville.

Things to do in Paducah

Parks · Museums · Historic Sites · Wineries

Side Trips

Hopkinsville

— 3 nights
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Step off the beaten path and head to Casey Jones Distillery and O.Z. Tyler Distillery. Explore Hopkinsville's surroundings by going to Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium (in Golden Pond) and Smothers Park (in Owensboro). There's still lots to do: identify plant and animal life at Pennyroyal Scuba Blue Springs Resort and let the kids burn off some steam at Christian Way Farm & Mini Golf.

For reviews, maps, and more tourist information, refer to the Hopkinsville online tour itinerary builder.

You can drive from Paducah to Hopkinsville in 1.5 hours. Expect a daytime high around 58°F in November, and nighttime lows around 38°F. Cap off your sightseeing on the 16th (Tue) early enough to travel to Mammoth Cave National Park.

Things to do in Hopkinsville

Parks · Wildlife · Breweries & Distilleries · Fun & Games

Side Trips

Mammoth Cave National Park

— 3 nights
Mammoth Caves National Park is the longest cave system in the world so far discovered.
Explore hidden gems such as Cedar Sink Trail and Nature & Wildlife Tours. There's still lots to do: explore the fascinating underground world of Mammoth Cave, get to know the resident critters at Kentucky Down Under Adventure Zoo, hike along Fat Man's Misery, and stroll through Tall Man's Misery.

To find maps, photos, ratings, and other tourist information, read Mammoth Cave National Park tour itinerary builder app.

Traveling by car from Hopkinsville to Mammoth Cave National Park takes 2 hours. In November in Mammoth Cave National Park, expect temperatures between 57°F during the day and 36°F at night. Finish your sightseeing early on the 19th (Fri) so you can drive to Lebanon.

Things to do in Mammoth Cave National Park

Parks · Outdoors · Trails · Nature

Side Trips

Lebanon

— 2 nights
Lebanon is a home rule-class city in Marion County, Kentucky, in the United States. Kick off your visit on the 20th (Sat): brush up on your knowledge of spirits at Wilderness Trail Distillery, examine the collection at The Great American Dollhouse Museum, and then sample the fine beverages at Limestone Branch Distillery. On the 21st (Sun), you'll have a packed day of sightseeing: sample the fine beverages at Maker's Mark and then steep yourself in history at Abraham Lincoln Birthplace National Historical Park.

Start your trip to Lebanon by creating a personalized itinerary on Inspirock.

You can drive from Mammoth Cave National Park to Lebanon in 2 hours. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In November, daily temperatures in Lebanon can reach 54°F, while at night they dip to 34°F. Finish your sightseeing early on the 21st (Sun) to allow enough time to travel to Middlesboro.

Things to do in Lebanon

Breweries & Distilleries · Historic Sites · Museums

Side Trips

Middlesboro

— 2 nights
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. On the 22nd (Mon), explore the striking landscape of Cumberland Gap National Historical Park. On the 23rd (Tue), you'll have a packed day of sightseeing: head outdoors with Visit Harlan County and then admire the sheer force of Cumberland Falls State Resort Park.

To see maps, more things to do, photos, and other tourist information, use the Middlesboro tour itinerary builder.

Drive from Lebanon to Middlesboro in 3 hours. Traveling from Lebanon to Middlesboro, you'll gain 1 hour due to the time zone difference. In November, daytime highs in Middlesboro are 58°F, while nighttime lows are 34°F. Finish up your sightseeing early on the 23rd (Tue) so you can travel to Lexington.

Things to do in Middlesboro

Nature · Parks · Outdoors

Side Trips

Lexington

— 7 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 Mary Todd Lincoln House and Distillery Tours. Explore Lexington's surroundings by going to Ark Encounter (in Williamstown), Natural Bridge State Resort Park (in Slade) and Red River Gorge Geological Area (in Winchester). There's much more to do: sample the fine beverages at Castle & Key Distillery, go for a walk through Kentucky Bourbon Trail, make a trip to Daniel Boone's Grave, and examine the collection at Aviation Museum of Kentucky.

To see reviews, maps, photos, and other tourist information, read our Lexington day trip tool.

Getting from Middlesboro to Lexington by car takes about 2.5 hours. You'll lose 1 hour traveling from Middlesboro to Lexington due to the time zone difference. Expect a daytime high around 56°F in November, and nighttime lows around 36°F. Wrap up your sightseeing on the 30th (Tue) early enough to drive back home.

Things to do in Lexington

Breweries & Distilleries · Historic Sites · Tours · Museums

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.