39 days in Kentucky Itinerary

39 days in Kentucky Itinerary

Created using Inspirock Kentucky planner
Make it your trip
Fly
1
Newport
— 2 nights
Drive
2
Louisville
— 10 nights
Drive
3
Paducah
— 6 nights
Drive
4
Bowling Green
— 7 nights
Drive
5
Lexington
— 9 nights
Drive
6
Corbin
— 4 nights
Fly

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Newport — 2 nights

Newport is a home rule-class city at the confluence of the Ohio and Licking rivers in Campbell County, Kentucky, in the United States. Change things up with a short trip to EarthJOY Tree Adventures in Germantown (about 1 hour away). Next up on the itinerary: observe the fascinating underwater world at Newport Aquarium, don't miss a visit to Roebling Murals on the Floodwalls of Covington, KY, have fun at George Rogers Clark Park, and walk around Devou Park.

To see where to stay, traveler tips, photos, and other tourist information, read Newport tour itinerary planner.

New York City to Newport is an approximately 3.5-hour flight. You can also fly; or drive; or take a bus. Expect little chillier evenings in Newport when traveling from New York City in October, with lows around 46°F. Finish your sightseeing early on the 6th (Wed) to allow enough time to drive to Louisville.
Parks · Fun & Games · Museums · Zoos & Aquariums
Side Trips

Louisville — 10 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Explore Louisville's surroundings by going to Bardstown (Barton 1792 Distillery & Lux Row Distillers), Maker's Mark (in Loretto) and Limestone Branch Distillery (in Lebanon). There's lots more to do: Head underground at Louisville Mega Cavern, snap pictures at The Big Four Bridge, see the interesting displays at Louisville Slugger Museum & Factory, and brush up on your knowledge of spirits at Copper & Kings American Brandy Distillery.

For traveler tips, photos, where to stay, and other tourist information, refer to the Louisville road trip planner.

Drive from Newport to Louisville in 2 hours. Alternatively, you can drive; or take a bus. In October in Louisville, expect temperatures between 71°F during the day and 50°F at night. Finish up your sightseeing early on the 16th (Sat) so you can go by car to Paducah.
Breweries & Distilleries · Parks · Museums · Tours
Side Trips

Paducah — 6 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Explore the numerous day-trip ideas around Paducah: The Arboretum at Murray State (in Murray), Woodlands Nature Station (in Cadiz) and Golden Pond (Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium & The Elk and Bison Prairie). And it doesn't end there: learn about winemaking at Purple Toad Winery, don't miss a visit to Floodwall Murals, admire the masterpieces at The National Quilt Museum, and stop by LowerTown Arts District.

To find maps, traveler tips, ratings, and more tourist information, read our Paducah trip planner.

You can drive from Louisville to Paducah in 4 hours. Alternatively, you can drive; or take a bus; or fly. Due to the time zone difference, you'll gain 1 hour traveling from Louisville to Paducah. In October, plan for daily highs up to 73°F, and evening lows to 50°F. Finish your sightseeing early on the 22nd (Fri) so you can drive to Bowling Green.
Parks · Wildlife · Museums · Historic Sites
Side Trips

Bowling Green — 7 nights

Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Change things up with these side-trips from Bowling Green: Owensboro (Reid's Orchard & Smothers Park), Mammoth Cave National Park (Mammoth Cave, Cedar Sink Trail, &more) and Hopkinsville (Casey Jones Distillery & Christian Way Farm & Mini Golf). There's lots more to do: explore the fascinating underground world of Lost River Cave, relax in the rural setting at Chaney's Dairy Barn, join the crowd at NCM Motorsports Park, and examine the collection at National Corvette Museum.

To see more things to do, traveler tips, and more tourist information, go to the Bowling Green online holiday planner.

Getting from Paducah to Bowling Green by car takes about 2.5 hours. Other options: take a bus. October in Bowling Green sees daily highs of 73°F and lows of 49°F at night. Finish your sightseeing early on the 29th (Fri) so you can drive to Lexington.
Parks · Nature · Trails · Outdoors
Side Trips

Lexington — 9 nights

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Venture out of the city with trips to Creation Museum (in Petersburg), Boone County Distilling Co. (in Independence) and Versailles (Woodford Reserve Distillery & Sun Valley Farm). The adventure continues: try your luck at Keeneland, sample the fine beverages at James E. Pepper Distillery, experience rural life at Mill Ridge Farm, and tour the pleasant surroundings at Salato Wildlife Education Center.

To find more things to do, ratings, reviews, and other tourist information, read Lexington vacation maker tool.

Traveling by car from Bowling Green to Lexington takes 3 hours. Alternatively, you can take a bus. The time zone difference when traveling from Bowling Green to Lexington is 1 hour. In October, daytime highs in Lexington are 70°F, while nighttime lows are 49°F. Finish your sightseeing early on the 7th (Sun) so you can drive to Corbin.
Breweries & Distilleries · Museums · Wildlife · Parks
Side Trips

Corbin — 4 nights

Corbin is a home rule-class city in Whitley and Knox counties in the southeastern portion of the U.S. state of Kentucky. Explore Corbin's surroundings by going to Wayne County Historical Museum (in Monticello), Cumberland Gap National Historical Park (in Middlesboro) and Split Bow Arch (in Stearns). There's much more to do: admire the sheer force of Cumberland Falls State Resort Park, stroll through Cumberland Point Recreational Area, and take an in-depth tour of Harland Sanders Cafe And Museum.

For where to stay, traveler tips, other places to visit, and tourist information, use the Corbin trip maker app.

You can drive from Lexington to Corbin in 1.5 hours. Alternatively, you can do a combination of bus and taxi. In November, daily temperatures in Corbin can reach 58°F, while at night they dip to 36°F. Finish your sightseeing early on the 11th (Thu) so you can fly back home.
Parks · Nature · Wildlife · Museums
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.