30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky trip builder

Make it your trip
Drive
1
Louisville
— 6 nights
Drive
2
Owensboro
— 3 nights
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3
Paducah
— 4 nights
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4
Hopkinsville
— 3 nights
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5
Bowling Green
— 5 nights
Drive
6
Lebanon
— 2 nights
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7
Middlesboro
— 1 night
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8
Lexington
— 5 nights
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Louisville

— 6 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. Get out of town with these interesting Louisville side-trips: Bardstown (My Old Kentucky Home, Willett Distilling Company, &more) and Bernheim Arboretum & Forest (in Clermont). There's still lots to do: stroll around Cherokee Park, sample the fine beverages at Copper & Kings American Brandy Distillery, admire the masterpieces at The Speed Art Museum, and stroll the grounds of Cave Hill Cemetery.

To see where to stay, photos, reviews, and more tourist information, read our Louisville travel planning website.

Columbus to Louisville is an approximately 3.5-hour car ride. You can also take a bus; or fly. In November, plan for daily highs up to 57°F, and evening lows to 37°F. Wrap up your sightseeing on the 7th (Sun) to allow time to travel to Owensboro.

Things to do in Louisville

Breweries & Distilleries · Museums · Parks · Historic Sites

Side Trips

Owensboro

— 3 nights
Owensboro is a home rule-class city in and the county seat of Daviess County, Kentucky, United States. Discover out-of-the-way places like O.Z. Tyler Distillery and Smothers Park. Venture out of the city with trips to Everly Brothers Monument (in Central City), Bill Monroe's Home Place (in Rosine) and Henderson (Audubon State Park & Ruby Moon Vineyard & Winery). There's more to do: stroll around Yellow Creek Park.

To see other places to visit, reviews, more things to do, and more tourist information, go to the Owensboro trip maker site.

You can drive from Louisville to Owensboro in 2 hours. You'll gain 1 hour traveling from Louisville to Owensboro due to the time zone difference. November in Owensboro sees daily highs of 56°F and lows of 37°F at night. Finish your sightseeing early on the 10th (Wed) to allow enough time to travel to Paducah.

Things to do in Owensboro

Parks · Nature · Wineries · Historic Sites

Side Trips

Paducah

— 4 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 Apple Valley Hillbilly Garden and Toyland. Take a break from Paducah with a short trip to Kentucky Lake in Gilbertsville, about 30 minutes away. And it doesn't end there: take a leisurely stroll along Paducah Riverwalk, make a trip to Floodwall Murals, look for gifts at Hancock's of Paducah, and get engrossed in the history at River Discovery Center.

For reviews, photos, more things to do, and tourist information, read Paducah trip itinerary planning site.

You can drive from Owensboro to Paducah in 2.5 hours. In November, plan for daily highs up to 59°F, and evening lows to 37°F. Wrap up your sightseeing on the 14th (Sun) early enough to drive to Hopkinsville.

Things to do in Paducah

Parks · Museums · Historic Sites · Childrens Museums

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 Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium. Explore the numerous day-trip ideas around Hopkinsville: The Elk and Bison Prairie (in Golden Pond), Robert Penn Warren Birthplace Museum (in Guthrie) and Adsmore House & Gardens (in Princeton). Next up on the itinerary: get outside with Pennyroyal Scuba Blue Springs Resort, stroll around Jefferson Davis Memorial Kentucky State Park, look for gifts at Griffin's Studio, and let little ones run wild at Christian Way Farm & Mini Golf.

To find reviews, where to stay, more things to do, and other tourist information, refer to the Hopkinsville travel route planner.

You can drive from Paducah to Hopkinsville in 1.5 hours. In November, plan for daily highs up to 58°F, and evening lows to 38°F. Cap off your sightseeing on the 17th (Wed) early enough to go by car to Bowling Green.

Things to do in Hopkinsville

Parks · Wildlife · Outdoors · Tours

Side Trips

Bowling Green

— 5 nights
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. You'll discover tucked-away gems like Cub Run Cave and Nature & Wildlife Tours. Change things up with these side-trips from Bowling Green: Dinosaur World (in Cave City), Horse Cave (Hidden River Cave and American Cave Museum & Kentucky Down Under Adventure Zoo) and Mammoth Cave National Park (Fat Man's Misery, Mammoth Cave, &more). And it doesn't end there: gain insight at Western Kentucky University, explore the fascinating underground world of Lost River Cave, bet on your favorite at NCM Motorsports Park, and get engrossed in the history at Aviation Heritage Park.

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

Traveling by car from Hopkinsville to Bowling Green takes 1.5 hours. November in Bowling Green sees daily highs of 59°F and lows of 37°F at night. Cap off your sightseeing on the 22nd (Mon) early enough to travel to Lebanon.

Things to do in Bowling Green

Parks · Nature · Outdoors · Museums

Side Trips

Lebanon

— 2 nights
Lebanon is a home rule-class city in Marion County, Kentucky, in the United States. On the 23rd (Tue), take in the history at Perryville Battlefield State Historic Site, then brush up on your knowledge of spirits at Wilderness Trail Distillery, then brush up on your knowledge of spirits at Maker's Mark, and finally sample the fine beverages at Limestone Branch Distillery. Keep things going the next day: contemplate the long history of Abraham Lincoln Birthplace National Historical Park, take in the spiritual surroundings of The Abbey of Gethsemani, and then examine the collection at The Great American Dollhouse Museum.

To see maps, reviews, where to stay, and other tourist information, read Lebanon tour site.

You can drive from Bowling Green to Lebanon in 2 hours. The time zone difference when traveling from Bowling Green to Lebanon is 1 hour. Traveling from Bowling Green in November, you will find days in Lebanon are a bit cooler (54°F), and nights are about the same (34°F). Wrap up your sightseeing on the 24th (Wed) to allow time to travel to Middlesboro.

Things to do in Lebanon

Historic Sites · Breweries & Distilleries · Museums

Side Trips

Middlesboro

— 1 night
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Kick off your visit on the 25th (Thu): explore the wealth of natural beauty at Cumberland Gap National Historical Park.

To find other places to visit, traveler tips, where to stay, and tourist information, go to the Middlesboro holiday builder.

Drive from Lebanon to Middlesboro in 3 hours. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. November in Middlesboro sees daily highs of 58°F and lows of 34°F at night. Cap off your sightseeing on the 25th (Thu) early enough to travel to Lexington.

Things to do in Middlesboro

Nature · Parks

Lexington

— 5 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.
Discover out-of-the-way places like Mary Todd Lincoln House and Red River Gorge Geological Area. Venture out of the city with trips to Fitchburg Furnace (in Ravenna), Natural Bridge State Resort Park (in Slade) and Frankfort (Daniel Boone's Grave & Castle & Key Distillery). The adventure continues: learn insider's secrets on a distillery tour, steep yourself in history at Shaker Village of Pleasant Hill, look for all kinds of wild species at Unique Horse Farm Tours, and walk around The Arboretum.

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

You can drive from Middlesboro to Lexington in 2.5 hours. You'll lose 1 hour traveling from Middlesboro to Lexington due to the time zone difference. In November, plan for daily highs up to 56°F, and evening lows to 36°F. Wrap up your sightseeing on the 30th (Tue) early enough to drive back home.

Things to do in Lexington

Historic Sites · Breweries & Distilleries · Parks · 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.