35 days in Kentucky Itinerary

35 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

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Route & dates

35 days in Kentucky Itinerary

Start: Nashville
Drive:  2​h 15​min
1
Cave City
— 4 nights
Drive:  1​h 15​min
2
Loretto
— 1 night
Drive:  2​h
3
Corbin
— 2 nights
Drive:  1​h 45​min
4
Lexington
— 9 nights
bus:  1​h 30​min
5
Newport
— 3 nights
Drive:  1​h 45​min
6
Louisville
— 9 nights
Drive:  3​h 45​min
7
Paducah
— 6 nights
Drive:  2​h 30​min
End: Nashville

4
nights
Cave City

Cave City ©
Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
Step out of the city life by going to Mammoth Cave National Park and Nature & Wildlife Tours. Visit Abraham Lincoln Birthplace National Historical Park and St. Joseph Catholic Church for their historical value. Get out of town with these interesting Cave City side-trips: Limestone Branch Distillery (in Lebanon), Lost River Cave (in Bowling Green) and Wolf Creek National Fish Hatchery (in Jamestown). There's still lots to do: see the interesting displays at National Corvette Museum, hike along Cedar Sink Trail, contemplate the long history of Bell's Tavern, and tour the pleasant surroundings at Fat Man's Misery.

To see other places to visit, photos, and tourist information, go to the Cave City day trip site .

Nashville to Cave City is an approximately 1.5-hour car ride. In October, plan for daily highs up to 71°F, and evening lows to 48°F. Finish your sightseeing early on the 17th (Thu) so you can drive to Loretto.

Things to do in Cave City

Parks Outdoors Nature

Side Trips

Mammoth Cave National Park, Bowling Green, Limestone Branch Distillery, Wolf Creek National Fish Hatchery, Abraham Lincoln Birthplace National Historical Park
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
National Corvette Museum ©
National Corvette Museum
Fat Man's Misery ©
Fat Man's Misery

1
night
Loretto

Loretto ©
Loretto is a home rule-class city in Marion County, Kentucky, United States. On the 18th (Fri), learn about winemaking at Springhill Winery, contemplate the long history of Abraham Lincoln Boyhood Home at Knob Creek, then take in the spiritual surroundings of The Abbey of Gethsemani, and finally sample the fine beverages at Maker's Mark.

To find reviews, more things to do, where to stay, and other tourist information, go to the Loretto tour itinerary planner .

You can drive from Cave City to Loretto in 1.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Cave City to Loretto. In October, plan for daily highs up to 68°F, and evening lows to 46°F. Finish your sightseeing early on the 18th (Fri) so you can travel to Corbin.

Things to do in Loretto

Historic Sites Breweries & Distilleries Wineries

Side Trips

Springhill Winery, Abraham Lincoln Boyhood Home at Knob Creek, The Abbey of Gethsemani
Highlights from your plan
Maker's Mark ©
Maker's Mark
The Abbey of Gethsemani ©
The Abbey of Gethsemani
Springhill Winery ©
Springhill Winery

2
nights
Corbin

Corbin ©
Corbin is a home rule-class city in Whitley and Knox counties in the southeastern portion of the U.S. On the 19th (Sat), do a tasting at Cedar Creek Vineyards, do a tasting at Cave Hill Vineyard & Winery, and then look for all kinds of wild species at Cumberland Point Recreational Area. Keep things going the next day: witness the site of a historic battle at Camp Wildcat Battlefield, admire the sheer force of Cumberland Falls State Resort Park, and then see the interesting displays at Blue Heron Interpretive Center.

To find other places to visit, photos, ratings, and other tourist information, read our Corbin travel route planner.

You can drive from Loretto to Corbin in 2.5 hours. In October in Corbin, expect temperatures between 71°F during the day and 48°F at night. Finish your sightseeing early on the 20th (Sun) to allow enough time to travel to Lexington.

Things to do in Corbin

Parks Nature Wineries

Side Trips

Cave Hill Vineyard & Winery, Blue Heron Interpretive Center, Camp Wildcat Battlefield, Cedar Creek Vineyards, Cumberland Point Recreational Area
Highlights from your plan
Cumberland Falls State Resort Park ©
Cumberland Falls State Resort Park
Blue Heron Interpretive Center ©
Blue Heron Interpretive Center

9
nights
Lexington

Lexington ©
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
You'll explore and learn at Kentucky Horse Park and Kentucky Artisan Center at Berea. Shaker Village of Pleasant Hill and Horseshoe Bend Vineyards and WineryHorseshoe Bend Vineyards and Winery are good opportunities to explore the local culture. Change things up with these side-trips from Lexington: Woodford Reserve Distillery (in Versailles), Frankfort (Rebecca Ruth Candy Tours & Museum, Salato Wildlife Education Center, & more) and Lawrenceburg (Wild Turkey Distillery, Four Roses, & more). There's much more to do: steep yourself in history at Mary Todd Lincoln House, indulge in some personalized pampering at some of the best spas, take in the dramatic natural features at Lower Howard's Creek Nature and Heritage Preserve, and indulge your thirst for a good beer at Lexington Brewing & Distilling Co..

To see reviews, photos, other places to visit, and more tourist information, refer to the Lexington road trip planning app .

You can drive from Corbin to Lexington in 2 hours. In October, plan for daily highs up to 70°F, and evening lows to 49°F. Finish up your sightseeing early on the 29th (Tue) so you can catcht the bus to Newport.

Things to do in Lexington

Parks Museums Historic Sites

Side Trips

Frankfort, Lawrenceburg, Versailles, Berea, Georgetown
Highlights from your plan
Kentucky Horse Park ©
Kentucky Horse Park
The Great American Dollhouse Museum ©
Buffalo Trace Distillery ©
Buffalo Trace Distillery

3
nights
Newport

Newport
Newport is a home rule-class city at the confluence of the Ohio and Licking rivers in Campbell County, Kentucky, in the United States. Do some cultural sightseeing at Ark Encounter and Vent Haven Museum. Explore the numerous day-trip ideas around Newport: EarthJOY Tree Adventures (in Germantown) and Verona Vineyards (in Verona). Next up on the itinerary: see the interesting displays at Creation Museum, steep yourself in history at MainStrasse Village, brush up on your knowledge of spirits at Boone County Distilling Company, and admire nature's wide array of creatures at Newport Aquarium.

To find reviews, more things to do, photos, and other tourist information, you can read our Newport holiday maker tool .

Take a bus from Lexington to Newport in 1.5 hours. Alternatively, you can drive. In October, daily temperatures in Newport can reach 68°F, while at night they dip to 46°F. Wrap up your sightseeing on the 1st (Fri) to allow time to drive to Louisville.

Things to do in Newport

Museums Zoos & Aquariums Parks

Side Trips

Ark Encounter, Verona Vineyards, Boone County Distilling Company, Vent Haven Museum, Creation Museum
Highlights from your plan
Ark Encounter
Ark Encounter
Creation Museum
Creation Museum
Vent Haven Museum ©
Vent Haven Museum

9
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Satisfy your inner culture vulture at Kentucky Derby Museum and Louisville Mega Cavern. Let the collections at Louisville Slugger Museum & Factory and Muhammad Ali Center capture your imagination. Change things up with these side-trips from Louisville: Bardstown (Willett Distilling Company, Old Bardstown Village Civil War Museum, & more), Clermont (Bernheim Arboretum & Forest & Jim Beam American Stillhouse) and Swope's Cars of Yesteryear Museum (in Elizabethtown). There's much more to do: try to win big at Churchill Downs, take a stroll through West Main Historic District, explore the different monuments and memorials at Cave Hill Cemetery, and brush up on your knowledge of spirits at Kentucky Peerless Distilling Co.

For ratings, reviews, maps, and more tourist information, you can read our Louisville vacation website .

Getting from Newport to Louisville by car takes about 2 hours. Other options: take a bus. In November in Louisville, expect temperatures between 57°F during the day and 37°F at night. Finish up your sightseeing early on the 10th (Sun) so you can go by car to Paducah.

Things to do in Louisville

Parks Historic Sites Wildlife

Side Trips

Bardstown, Clermont, Jefferson Memorial Forest, Saunders Springs Nature Preserve, Swope's Cars of Yesteryear Museum
Highlights from your plan
Louisville Slugger Museum & Factory ©
Kentucky Derby Museum ©
Kentucky Derby Museum
Churchill Downs ©
Churchill Downs

6
nights
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Get some historical perspective at William Clark Market House Museum and Paducah Riverwalk. Get in touch with nature at Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium and The Arboretum at Murray State. Get out of town with these interesting Paducah side-trips: The Elk and Bison Prairie (in Golden Pond), Henderson (Farmer and Frenchman Winery & Ruby Moon Vineyard & Winery) and Woodlands Nature Station (in Cadiz). There's still lots to do: do a tasting at Purple Toad Winery, get curious at Ben E. Clement Mineral Museum, brush up on your knowledge of spirits at Casey Jones Distillery, and identify plant and animal life at Jeffers Bend Environmental Center.

To see maps, more things to do, traveler tips, and tourist information, go to the Paducah tour itinerary app .

You can drive from Louisville to Paducah in 4 hours. Other options are to fly; or take a bus. The time zone difference when traveling from Louisville to Paducah is minus 1 hour. November in Paducah sees daily highs of 59°F and lows of 37°F at night. Wrap up your sightseeing on the 16th (Sat) to allow time to drive back home.

Things to do in Paducah

Parks Wildlife Museums

Side Trips

Golden Pond, Hopkinsville, Henderson, Newsom's Old Mill Store, Apple Valley Hillbilly Garden and Toyland
Highlights from your plan
Casey Jones Distillery ©
Casey Jones Distillery
The National Quilt Museum ©
The National Quilt Museum
Purple Toad Winery ©
Purple Toad Winery

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