30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky holiday planner
Make it your trip
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1
Louisville
— 5 nights
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2
Owensboro
— 3 nights
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3
Paducah
— 3 nights
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4
Hopkinsville
— 3 nights
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5
Bowling Green
— 4 nights
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6
Lebanon
— 2 nights
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7
Middlesboro
— 2 nights
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8
Lexington
— 7 nights
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Louisville — 5 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Explore hidden gems such as Conrad-Caldwell House Museum (Conrad's Castle) and Bernheim Arboretum & Forest. You'll find plenty of places to visit near Louisville: Elizabethtown (Swope's Cars of Yesteryear Museum & Freeman Lake Park) and Bardstown (Old Bardstown Village Civil War Museum, Willett Distilling Company, &more). The adventure continues: walk around Cherokee Park, sample the fine beverages at Angel's Envy Distillery, stroll the grounds of Cave Hill Cemetery, and get thoroughly spooked out with a ghost and vampire tour.

To see maps, photos, more things to do, and tourist information, refer to the Louisville travel route planner.

Columbus to Louisville is an approximately 3.5-hour car ride. You can also take a bus; or fly. November in Louisville sees daily highs of 57°F and lows of 37°F at night. Wrap up your sightseeing on the 6th (Sat) early enough to travel to Owensboro.
Breweries & Distilleries · Museums · Parks · Tours
Side Trips

Owensboro — 3 nights

Owensboro is a home rule-class city in and the county seat of Daviess County, Kentucky, United States. Eschew the tourist crowds and head to O.Z. Tyler Distillery and Rough River State Park. Get out of town with these interesting Owensboro side-trips: Henderson (John James Audubon Museum & Audubon State Park). There's still lots to do: walk around Smothers Park, relax in the rural setting at Trunnell's Farm Market & Family Fun Acre, bet on your favorite at Kentucky Motor Speedway, and see the interesting displays at Owensboro Museum of Science and History.

Quickly create a custom-made itinerary for Owensboro using our trip planner.

Drive from Louisville to Owensboro in 2 hours. The time zone difference when traveling from Louisville to Owensboro is minus 1 hour. Expect a daytime high around 56°F in November, and nighttime lows around 37°F. Wrap up your sightseeing on the 9th (Tue) to allow time to travel to Paducah.
Parks · Museums · Nature · Breweries & Distilleries
Side Trips

Paducah — 3 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. You'll explore the less-touristy side of things at Purple Toad Winery and LowerTown Arts District. Change things up with a short trip to Kentucky Lake in Gilbertsville (about 30 minutes away). There's much more to do: get to know the fascinating history of Paducah Riverwalk, walk around Bob Noble Park, explore the engaging exhibits at River Discovery Center, and admire the engineering at Kentucky Dam.

To find ratings, reviews, photos, and tourist information, you can read our Paducah road trip planning app.

Drive from Owensboro to Paducah in 2.5 hours. In November, daytime highs in Paducah are 59°F, while nighttime lows are 37°F. Wrap up your sightseeing on the 12th (Fri) early enough to drive to Hopkinsville.
Parks · Historic Sites · Museums · Shopping
Side Trips

Hopkinsville — 3 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. You'll discover tucked-away gems like Casey Jones Distillery and Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium. Change things up with these side-trips from Hopkinsville: The Elk and Bison Prairie (in Golden Pond), Newsom's Old Mill Store (in Princeton) and Ruby Laffoon Log Cabin (in Madisonville). The adventure continues: look for all kinds of wild species at Pennyroyal Scuba Blue Springs Resort, tour the pleasant surroundings at Jeffers Bend Environmental Center, pause for some photo ops at Jefferson Davis State Historic Site, and admire the majestic nature at Pennyrile Forest State Resort Park.

To see other places to visit, maps, where to stay, and other tourist information, read our Hopkinsville online trip builder.

Traveling by car from Paducah to Hopkinsville takes 1.5 hours. In November, plan for daily highs up to 58°F, and evening lows to 38°F. Wrap up your sightseeing on the 15th (Mon) early enough to drive to Bowling Green.
Wildlife · Parks · Tours · Outdoors
Side Trips

Bowling Green — 4 nights

Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Explore hidden gems such as Cub Run Cave and Aviation Heritage Park. You'll find plenty of places to visit near Bowling Green: Horse Cave (Kentucky Down Under Adventure Zoo & Hidden River Cave and American Cave Museum), Diamond Caverns (in Park City) and Dinosaur World (in Cave City). There's lots more to do: bet on your favorite at NCM Motorsports Park, surround yourself with nature on a nature and wildlife tour, stroll through Cedar Sink Trail, and hike along Fat Man's Misery.

To find traveler tips, where to stay, ratings, and other tourist information, you can read our Bowling Green road trip planner.

Traveling by car from Hopkinsville to Bowling Green takes 1.5 hours. In November, daytime highs in Bowling Green are 59°F, while nighttime lows are 37°F. Wrap up your sightseeing on the 19th (Fri) early enough to travel to Lebanon.
Parks · Outdoors · Nature · Museums
Side Trips

Lebanon — 2 nights

Lebanon is a home rule-class city in Marion County, Kentucky, in the United States. On the 20th (Sat), take in the history at Perryville Battlefield State Historic Site, then examine the collection at The Great American Dollhouse Museum, and then contemplate the long history of Old Fort Harrod State Park. Get ready for a full day of sightseeing on the next day: steep yourself in history at Abraham Lincoln Birthplace National Historical Park, contemplate in the serene atmosphere at The Abbey of Gethsemani, and then brush up on your knowledge of spirits at Limestone Branch Distillery.

To see ratings, maps, photos, and tourist information, refer to the Lebanon trip itinerary maker tool.

Drive from Bowling Green to Lebanon in 2 hours. The time zone difference when traveling from Bowling Green to Lebanon is 1 hour. Expect little chillier weather when traveling from Bowling Green in November: highs in Lebanon hover around 54°F, while lows dip to 34°F. Wrap up your sightseeing on the 21st (Sun) early enough to travel to Middlesboro.
Historic Sites · Breweries & Distilleries · 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: walk around Sanders Park, get engrossed in the history at Harland Sanders Cafe And Museum, and then immerse yourself in nature at Pine Mountain State Resort Park.

For more things to do, photos, and more tourist information, use the Middlesboro trip itinerary maker.

Getting from Lebanon to Middlesboro by car takes about 3 hours. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In November, daytime highs in Middlesboro are 58°F, while nighttime lows are 34°F. Finish your sightseeing early on the 23rd (Tue) to allow enough time to travel to Lexington.
Parks · Nature · Museums
Side Trips

Lexington — 7 nights

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 Kentucky Bourbon Trail. Venture out of the city with trips to Frankfort (Kentucky Vietnam Veterans Memorial, Castle & Key Distillery, &more), Slade (Rock Bridge Trail #207 & Natural Bridge State Resort Park) and Red River Gorge Geological Area (in Winchester). And it doesn't end there: gain some tasty knowledge on a distillery tour, experience rural life at Claiborne Farm, stroll the grounds of Lexington Cemetery, and stroll through Raven Run Nature Sanctuary.

For where to stay, reviews, more things to do, and more tourist information, read our Lexington road trip website.

Traveling by car from Middlesboro to Lexington takes 2.5 hours. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect a daytime high around 56°F in November, and nighttime lows around 36°F. Finish up your sightseeing early on the 30th (Tue) so you can go by car back home.
Breweries & Distilleries · Parks · Historic Sites · Tours
Side Trips

Kentucky travel guide

4.6
Caves · Distilleries · Specialty Museums
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.