30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky holiday planner

Make it your trip
Drive
1
Louisville
— 5 nights
Drive
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

Derby City

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 Kentucky Peerless Distilling Co. You'll find plenty of places to visit near Louisville: Elizabethtown (Swope's Cars of Yesteryear Museum & Freeman Lake Park), Bardstown (Old Bardstown Village Civil War Museum, Willett Distilling Company, &more) and Bernheim Arboretum & Forest (in Clermont). The adventure continues: walk around Cherokee Park, explore the different monuments and memorials at Cave Hill Cemetery, brush up on your knowledge of spirits at Old Forester Distilling, and see the interesting displays at Frazier History Museum.

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.

Things to do in Louisville

Breweries & Distilleries · Parks · Museums · 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 Owensboro Museum of Science and History. Get out of town with these interesting Owensboro side-trips: Rough River State Park (in Falls of Rough) and Henderson (John James Audubon Museum & Audubon State Park). There's still lots to do: walk around Smothers Park, join the crowd at Kentucky Motor Speedway, experience rural life at Trunnell's Farm Market & Family Fun Acre, and pick up a one of a kind souvenir at Don's Consignment.

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.

Things to do in Owensboro

Parks · Nature · Museums · Shopping

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 Paducah Riverwalk. Change things up with a short trip to Kentucky Lake in Gilbertsville (about 30 minutes away). And it doesn't end there: take an in-depth tour of River Discovery Center, see human ingenuity at work at Kentucky Dam, stop by Hancock's of Paducah, and stroll through Apple Valley Hillbilly Garden and Toyland.

To see ratings, maps, where to stay, and tourist information, read Paducah trip planner.

Traveling by car from Owensboro to Paducah takes 2.5 hours. In November in Paducah, expect temperatures between 59°F during the day and 37°F at night. Wrap up your sightseeing on the 12th (Fri) to allow time to drive to Hopkinsville.

Things to do in Paducah

Parks · Historic Sites · Shopping · Neighborhoods

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: Newsom's Old Mill Store (in Princeton), The Elk and Bison Prairie (in Golden Pond) and Ruby Laffoon Log Cabin (in Madisonville). The adventure continues: look for all kinds of wild species at Pennyroyal Scuba Blue Springs Resort, admire the majestic nature at Pennyrile Forest State Resort Park, pause for some photo ops at Jefferson Davis State Historic Site, and tour the pleasant surroundings at Jeffers Bend Environmental Center.

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.

Things to do in Hopkinsville

Wildlife · Parks · Outdoors · Tours

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 Western Kentucky University. 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). The adventure continues: hike along Cedar Sink Trail, bet on your favorite at NCM Motorsports Park, experience rural life at Chaney's Dairy Barn, and stroll through Fat Man's Misery.

To find other places to visit, reviews, maps, and more tourist information, read our Bowling Green trip itinerary planning app.

You can drive from Hopkinsville to Bowling Green in 1.5 hours. November in Bowling Green sees daily highs of 59°F and lows of 37°F at night. Finish your sightseeing early on the 19th (Fri) to allow enough time to travel to Lebanon.

Things to do in Bowling Green

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.

Things to do in Lebanon

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.

Things to do in Middlesboro

Parks · Nature · Museums

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 Red River Gorge Geological Area. Venture out of the city with trips to Slade (Rock Bridge Trail #207 & Natural Bridge State Resort Park), Frankfort (Kentucky Vietnam Veterans Memorial, Castle & Key Distillery, &more) and Claiborne Farm (in Paris). And it doesn't end there: gain some tasty knowledge on a distillery tour, indulge your thirst for a good beer at Lexington Brewing & Distilling Co., stroll the grounds of Lexington Cemetery, and take in the pleasant sights at Kentucky Bourbon Trail.

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.

Things to do in Lexington

Breweries & Distilleries · Parks · Historic Sites · Tours

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.