30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky itinerary builder

Make it your trip
Fly
1
Paducah
— 4 nights
Drive
2
Hopkinsville
— 3 nights
Drive
3
Cave City
— 6 nights
Drive
4
Louisville
— 7 nights
Drive
5
Middlesboro
— 2 nights
Drive
6
Lexington
— 7 nights
Drive

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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 Kentucky Dam. Explore the numerous day-trip ideas around Paducah: Wickliffe Mounds State Historic Site (in Wickliffe) and Audubon State Park (in Henderson). And it doesn't end there: take a leisurely stroll along Paducah Riverwalk, stop by Hancock's of Paducah, have fun and explore at River Discovery Center, and take in nature's colorful creations at Apple Valley Hillbilly Garden and Toyland.

For reviews, ratings, more things to do, and tourist information, refer to the Paducah trip maker app.

Columbus to Paducah is an approximately 5.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Columbus to Paducah. When traveling from Columbus in November, plan for a bit warmer days in Paducah, with highs around 59°F, while nights are about the same with lows around 37°F. Wrap up your sightseeing on the 5th (Fri) to allow time to drive to Hopkinsville.

Things to do in Paducah

Parks · Historic Sites · Nature · Wineries

Side Trips

Hopkinsville

— 3 nights
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Eschew the tourist crowds and head to Casey Jones Distillery and Lake Malone State Park. Change things up with these side-trips from Hopkinsville: Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium (in Golden Pond), Owensboro (O.Z. Tyler Distillery & Smothers Park) and Pennyrile Forest State Resort Park (in Dawson Springs).

To see ratings, other places to visit, traveler tips, and other tourist information, use the Hopkinsville vacation planning app.

Traveling by car from Paducah to Hopkinsville takes 1.5 hours. November in Hopkinsville sees daily highs of 58°F and lows of 38°F at night. Wrap up your sightseeing on the 8th (Mon) to allow time to travel to Cave City.

Things to do in Hopkinsville

Parks · Breweries & Distilleries · Nature · Wildlife

Side Trips

Cave City

— 6 nights
Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
Step off the beaten path and head to Limestone Branch Distillery and Swope's Cars of Yesteryear Museum. Explore the numerous day-trip ideas around Cave City: Abraham Lincoln Birthplace National Historical Park (in Hodgenville), Freeman Lake Park (in Elizabethtown) and Cub Run Cave (in Cub Run). And it doesn't end there: hike along Cedar Sink Trail, Head underground at Hidden River Cave and American Cave Museum, tour the pleasant surroundings at Fat Man's Misery, and get a dose of the wild on a nature and wildlife tour.

To see where to stay, photos, and tourist information, go to the Cave City travel app.

Getting from Hopkinsville to Cave City by car takes about 2 hours. In November, daily temperatures in Cave City can reach 57°F, while at night they dip to 36°F. Finish your sightseeing early on the 14th (Sun) to allow enough time to drive to Louisville.

Things to do in Cave City

Parks · Outdoors · Nature · Museums

Side Trips

Louisville

— 7 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Eschew the tourist crowds and head to Conrad-Caldwell House Museum (Conrad's Castle) and Frazier History Museum. Venture out of the city with trips to Bardstown (Distillery Tours, Old Bardstown Village Civil War Museum, &more) and Bernheim Arboretum & Forest (in Clermont). Next up on the itinerary: stroll around Cherokee Park, view the masterpieces at Mark Payton Glass Center @ The Glassworks Bldg, get thoroughly spooked out with a ghost and vampire tour, and sample the fine beverages at Kentucky Peerless Distilling Co.

To see ratings, more things to do, other places to visit, and more tourist information, read our Louisville trip planner.

Traveling by car from Cave City to Louisville takes 1.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of taxi and bus. Due to the time zone difference, you'll lose 1 hour traveling from Cave City to Louisville. In November, daily temperatures in Louisville can reach 57°F, while at night they dip to 37°F. Finish up your sightseeing early on the 21st (Sun) so you can travel to Middlesboro.

Things to do in Louisville

Breweries & Distilleries · Parks · Museums · Historic Sites

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: take an in-depth tour of Harland Sanders Cafe and Museum and then take a peaceful walk through Pine Mountain State Resort Park.

To find traveler tips, maps, reviews, and other tourist information, go to the Middlesboro online journey planner.

Getting from Louisville to Middlesboro by car takes about 3.5 hours. The time zone difference when traveling from Louisville to Middlesboro is minus 1 hour. In November in Middlesboro, expect temperatures between 58°F during the day and 34°F at night. Cap off your sightseeing on the 23rd (Tue) early enough 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 The Great American Dollhouse Museum. Venture out of the city with trips to Natural Bridge State Resort Park (in Slade), Frankfort (Castle & Key Distillery, Daniel Boone's Grave, &more) and Red River Gorge Geological Area (in Winchester). Next up on the itinerary: gain some tasty knowledge on a distillery tour, sample the fine beverages at James E. Pepper Distillery, contemplate the long history of Shaker Village of Pleasant Hill, and stroll the grounds of Lexington Cemetery.

To see where to stay, other places to visit, reviews, and more tourist information, go to the Lexington trip itinerary builder tool.

Drive from Middlesboro to Lexington in 2.5 hours. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Expect a daytime high around 56°F in November, and nighttime lows around 36°F. Finish your sightseeing early on the 30th (Tue) to allow enough time 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.