30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner
Make it your trip
Fly
1
Paducah
— 4 nights
Drive
2
Hopkinsville
— 4 nights
Drive
3
Bowling Green
— 6 nights
Drive
4
Louisville
— 7 nights
Drive
5
Lebanon
— 2 nights
Drive
6
Lexington
— 6 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. Go for a jaunt from Paducah to Henderson to see Audubon State Park about 1h 45 min away. And it doesn't end there: learn about winemaking at Purple Toad Winery, take in the waterfront at Paducah Riverwalk, examine the collection at Paducah Distilled Spirits, and take an in-depth tour of Lloyd Tilghman House and Civil War Museum.

To see traveler tips, more things to do, and tourist information, you can read our Paducah trip builder website.

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. Expect a bit warmer weather when traveling from Columbus in November: highs in Paducah hover around 59°F, while lows dip to 37°F. Finish up your sightseeing early on the 5th (Fri) so you can go by car to Hopkinsville.
Museums · Historic Sites · Parks · Wineries
Side Trips

Hopkinsville — 4 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Explore Hopkinsville's surroundings by going to Everly Brothers Monument (in Central City), Adsmore House & Gardens (in Princeton) and Golden Pond (Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium & The Elk and Bison Prairie). There's still lots to do: sample the fine beverages at Casey Jones Distillery, stop by Griffin's Studio, discover the deep blue sea with Pennyroyal Scuba Blue Springs Resort, and stroll through Christian Way Farm & Mini Golf.

To see traveler tips, more things to do, ratings, and tourist information, read our Hopkinsville itinerary builder 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. Finish your sightseeing early on the 9th (Tue) so you can drive to Bowling Green.
Parks · Wildlife · Fun & Games · Tours
Side Trips

Bowling Green — 6 nights

Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Get out of town with these interesting Bowling Green side-trips: Owensboro (O.Z. Tyler Distillery & Smothers Park), Cub Run Cave (in Cub Run) and Mammoth Cave National Park (Mammoth Cave, Cedar Sink Trail, &more). There's still lots to do: examine the collection at National Corvette Museum, join the crowd at NCM Motorsports Park, take an in-depth tour of South Union Shaker Village, and Head underground at Lost River Cave.

Before you visit Bowling Green, use our trip planner to discover what you can do and see there.

You can drive from Hopkinsville to Bowling Green in 1.5 hours. In November in Bowling Green, expect temperatures between 59°F during the day and 37°F at night. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Louisville.
Parks · Nature · Outdoors · Trails
Side Trips

Louisville — 7 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Change things up with these side-trips from Louisville: Bardstown (Willett Distilling Company & Barton 1792 Distillery), James B. Beam Distilling Co. (in Clermont) and Swope's Cars of Yesteryear Museum (in Elizabethtown). And it doesn't end there: Head underground at Louisville Mega Cavern, contemplate the long history of Conrad-Caldwell House Museum (Conrad's Castle), brush up on your knowledge of spirits at Evan Williams Bourbon Experience, and see the interesting displays at Kentucky Derby Museum.

To see photos, traveler tips, and tourist information, read Louisville trip planner.

Traveling by car from Bowling Green to Louisville takes 2 hours. Alternatively, you can take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In November in Louisville, expect temperatures between 57°F during the day and 37°F at night. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Lebanon.
Breweries & Distilleries · Museums · Historic Sites · Tours
Side Trips

Lebanon — 2 nights

Lebanon is a home rule-class city in Marion County, Kentucky, in the United States. On the 23rd (Tue), brush up on your knowledge of spirits at Maker's Mark and then brush up on your knowledge of spirits at Limestone Branch Distillery. Get ready for a full day of sightseeing on the 24th (Wed): brush up on your knowledge of spirits at Wilderness Trail Distillery, examine the collection at The Great American Dollhouse Museum, and then steep yourself in history at William Whitley House.

To see more things to do, other places to visit, ratings, and more tourist information, read Lebanon road trip site.

Drive from Louisville to Lebanon in 1.5 hours. In November, daytime highs in Lebanon are 54°F, while nighttime lows are 34°F. Finish your sightseeing early on the 24th (Wed) to allow enough time to drive to Lexington.
Breweries & Distilleries · Historic Sites · Museums
Side Trips

Lexington — 6 nights

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Change things up with these side-trips from Lexington: Frankfort (Buffalo Trace Distillery & Castle & Key Distillery), Versailles (Woodford Reserve Distillery & Sun Valley Farm) and Ark Encounter (in Williamstown). There's still lots to do: try to win big at Keeneland, immerse yourself in nature at Cumberland Falls State Resort Park, examine the collection at Kentucky Music Hall of Fame, and make a trip to Kentucky Horse Park.

Plan a Lexington trip in moments using our itinerary builder.

Getting from Lebanon to Lexington by car takes about 1.5 hours. In November in Lexington, expect temperatures between 56°F during the day and 36°F at night. Finish your sightseeing early on the 30th (Tue) so you can drive back home.
Breweries & Distilleries · Museums · Tours · Nature
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.