30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky trip builder
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1
Louisville
— 6 nights
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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
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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

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). The adventure continues: Head underground at Louisville Mega Cavern, brush up on your knowledge of spirits at Copper & Kings American Brandy Distillery, see the interesting displays at Louisville Slugger Museum & Factory, and get thoroughly spooked out with a ghost and vampire tour.

To find traveler tips, maps, and tourist information, read our Louisville holiday planner.

Columbus to Louisville is an approximately 3.5-hour car ride. You can also take a bus; or fly. In November in Louisville, expect temperatures between 57°F during the day and 37°F at night. Finish your sightseeing early on the 7th (Sun) to allow enough time to travel to Owensboro.
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 Panther 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.
Parks · Breweries & Distilleries · Historic Sites · Nature
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 The National Quilt Museum and Purple Toad Winery. Take a break from Paducah with a short trip to Kentucky Lake in Gilbertsville, about 30 minutes away. And it doesn't end there: make a trip to Floodwall Murals, have fun and explore at River Discovery Center, see human ingenuity at work at Kentucky Dam, and get to know the fascinating history of Paducah Riverwalk.

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.
Parks · Museums · Historic Sites · Shopping
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 Christian Way Farm & Mini Golf. Explore the numerous day-trip ideas around Hopkinsville: Golden Pond (The Elk and Bison Prairie & Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium), Robert Penn Warren Birthplace Museum (in Guthrie) and Adsmore House & Gardens (in Princeton). And it doesn't end there: head outdoors with Pennyroyal Scuba Blue Springs Resort, stop by Griffin's Studio, and tour the pleasant surroundings at Jefferson Davis Memorial Kentucky State Park.

For more things to do, other places to visit, photos, and more tourist information, refer to the Hopkinsville trip planner.

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 17th (Wed) early enough to go by car to Bowling Green.
Parks · Wildlife · Tours · Outdoors
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: Horse Cave (Hidden River Cave and American Cave Museum & Kentucky Down Under Adventure Zoo), Mammoth Cave National Park (Fat Man's Misery, Mammoth Cave, &more) and Dinosaur World (in Cave City). And it doesn't end there: join the crowd at NCM Motorsports Park, explore the fascinating underground world of Lost River Cave, deepen your understanding at Western Kentucky University, 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.
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.
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.
Nature · Parks

Lexington — 5 nights

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 Frankfort (Daniel Boone's Grave & Castle & Key Distillery), Natural Bridge State Resort Park (in Slade) and Fitchburg Furnace (in Ravenna). And it doesn't end there: gain some tasty knowledge on a distillery tour, relax in the rural setting at Old Friends at Dream Chase Farm, indulge your thirst for a good beer at Lexington Brewing & Distilling Co., and go for a walk through Kentucky Bourbon Trail.

To see photos, other places to visit, maps, and tourist information, read our Lexington trip planner.

Getting from Middlesboro to Lexington by car takes about 2.5 hours. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. November in Lexington sees daily highs of 56°F and lows of 36°F at night. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive back home.
Historic Sites · Breweries & Distilleries · Parks · 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.