25 days in Kentucky Itinerary

25 days in Kentucky Itinerary

Created using Inspirock Kentucky travel planner

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Route & dates

25 days in Kentucky Itinerary

Start: New York City
+2
Drive + Fly + Drive:  6​h 15​min
1
Cadiz
— 3 nights
Drive:  2​h 15​min
2
Mammoth Cave National Park
— 5 nights
Drive:  1​h 30​min
3
Bardstown
— 4 nights
Drive:  2​h 45​min
4
Middlesboro
— 3 nights
Drive:  1​h 45​min
5
Berea
— 4 nights
Drive:  1​h 15​min
6
Georgetown
— 5 nights
+2
Drive + Fly + Drive:  4​h 45​min
End: New York City

3
nights
Cadiz

Cadiz ©
Cadiz is a home rule-class city in and the county seat of Trigg County, Kentucky, United States. Popular historic sites such as St. Francis de Sales Catholic Church and Apple Valley Hillbilly Garden and Toyland are in your itinerary. Get outdoors at Columbus-Belmont State Park and Kentucky Lake. Explore Cadiz's surroundings by going to Paducah (Paducah Distilled Spirits, Paducah Riverwalk, & more). It doesn't end there: identify plant and animal life at Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium.

To see other places to visit, more things to do, and other tourist information, refer to the Cadiz trip planner .

New York City to Cadiz is an approximately 6.5-hour flight. You can also drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Traveling from New York City in October, plan for a bit cooler nights in Cadiz, with lows around 51°F. Cap off your sightseeing on the 4th (Thu) early enough to travel to Mammoth Cave National Park.

Things to do in Cadiz

Parks Nature Historic Sites

Side Trips

Paducah, Kentucky Lake, Apple Valley Hillbilly Garden and Toyland, Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium, Columbus-Belmont State Park
Highlights from your plan

5
nights
Mammoth Cave National Park

Mammoth Cave National Park ©
Mammoth Caves National Park is the longest cave system in the world so far discovered.
Visiting Mammoth Cave National Park and Wolf Creek National Fish Hatchery will get you outdoors. Let the collections at South Union Shaker Village and Hidden River Cave and American Cave Museum capture your imagination. Explore Mammoth Cave National Park's surroundings by going to Cub Run (Cub Run Cave & Detweiler's Country Store), Bowling Green (Historic RailPark and Train Museum, National Corvette Museum, & more) and Lake Cumberland State Resort Park (in Jamestown). There's still lots to do: examine the collection at Dinosaur World, explore the fascinating underground world of Onyx Cave, and tour the pleasant surroundings at Fat Man's Misery.

To see ratings, reviews, where to stay, and tourist information, use the Mammoth Cave National Park online sightseeing planner .

Drive from Cadiz to Mammoth Cave National Park in 2.5 hours. In October, daytime highs in Mammoth Cave National Park are 71°F, while nighttime lows are 48°F. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Bardstown.

Things to do in Mammoth Cave National Park

Parks Nature Museums

Side Trips

Bowling Green, Cub Run, Cave City, Jamestown, Diamond Caverns
Highlights from your plan
Fat Man's Misery ©
Fat Man's Misery
Aviation Heritage Park ©
Aviation Heritage Park
Dinosaur World ©
Dinosaur World

4
nights
Bardstown

Bardstown ©
Bardstown is a home rule-class city in Nelson County, Kentucky, in the United States. Do some cultural sightseeing at Louisville Mega Cavern and The Abbey of Gethsemani. Museum-lovers will appreciate Conrad-Caldwell House Museum (Conrad's Castle) and 21c Museum Hotel. Venture out of the city with trips to Louisville (Old Louisville, Churchill Downs, & more), Swope's Cars of Yesteryear Museum (in Elizabethtown) and Perryville Battlefield State Historic Site (in Perryville). The adventure continues: admire the majestic nature at My Old Kentucky Home, sample the fine beverages at Limestone Branch Distillery, and contemplate the long history of Abraham Lincoln Boyhood Home at Knob Creek.

To see photos, where to stay, maps, and more tourist information, refer to the Bardstown day trip planning site .

You can drive from Mammoth Cave National Park to Bardstown in 1.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Mammoth Cave National Park to Bardstown. In October, plan for daily highs up to 69°F, and evening lows to 48°F. Finish your sightseeing early on the 13th (Sat) to allow enough time to travel to Middlesboro.

Things to do in Bardstown

Historic Sites Museums Outdoors

Side Trips

Louisville, Limestone Branch Distillery, Swope's Cars of Yesteryear Museum, Perryville Battlefield State Historic Site, Abraham Lincoln Boyhood Home at Knob Creek
Highlights from your plan
Swope's Cars of Yesteryear Museum ©
Swope's Cars of Yesteryear Museum
The Abbey of Gethsemani ©
The Abbey of Gethsemani

3
nights
Middlesboro

Middlesboro ©
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Discover out-of-the-way places like Cumberland Gap National Historical Park and Harland Sanders Cafe and Museum. Escape the urban bustle at Yahoo Falls and Pine Mountain State Resort Park. Get out of town with these interesting Middlesboro side-trips: Dr. Thomas Walker State Historic Site (in Barbourville), Sanders Park (in Corbin) and McCreary County Museum (in Stearns). There's more to do: appreciate the extensive heritage of Natural Arch Scenic Area.

To see photos, where to stay, and more tourist information, you can read our Middlesboro travel itinerary planner.

You can drive from Bardstown to Middlesboro in 3 hours. Due to the time zone difference, you'll gain 1 hour traveling from Bardstown to Middlesboro. Expect a daytime high around 71°F in October, and nighttime lows around 47°F. Finish your sightseeing early on the 16th (Tue) so you can travel to Berea.

Things to do in Middlesboro

Parks Nature Historic Sites

Side Trips

Corbin, Whitley City, McCreary County Museum, Dr. Thomas Walker State Historic Site, Pine Mountain State Resort Park
Highlights from your plan
Cumberland Gap National Historical Park ©
Pine Mountain State Resort Park ©
Pine Mountain State Resort Park
Harland Sanders Cafe and Museum ©
Harland Sanders Cafe and Museum

4
nights
Berea

Berea ©
Berea is a home rule-class city in Madison County, Kentucky, in the United States. Get a sense of the local culture at Shaker Village of Pleasant Hill and Three Forks Historical Center. Kentucky Artisan Center at Berea and The Great American Dollhouse Museum will appeal to museum buffs. Explore Berea's surroundings by going to Old Fort Harrod State Park (in Harrodsburg), Levi Jackson Wilderness Road State Park (in London) and Kentucky Rock & Adventure Guides (in Pine Ridge). There's much more to do: contemplate the long history of White Hall State Historic Site, explore and take pictures at Nada Tunnel, take in the exciting artwork at Berea Arts Council, and take a peaceful walk through Berea Pinnacles.

For ratings, other places to visit, traveler tips, and tourist information, read our Berea trip itinerary planner.

Traveling by car from Middlesboro to Berea takes 2 hours. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Traveling from Middlesboro in October, you will find days in Berea are slightly colder (66°F), and nights are about the same (48°F). Wrap up your sightseeing on the 20th (Sat) to allow time to travel to Georgetown.

Things to do in Berea

Parks Nature Museums

Side Trips

Harrodsburg, Kentucky Rock & Adventure Guides, White Hall State Historic Site, Three Forks Historical Center, Nada Tunnel
Highlights from your plan
Old Fort Harrod State Park ©
Old Fort Harrod State Park
Shaker Village of Pleasant Hill ©
Shaker Village of Pleasant Hill
The Great American Dollhouse Museum ©

5
nights
Georgetown

Georgetown ©
Georgetown is a home rule-class city in Scott County, Kentucky, in the United States. Your inner history buff will appreciate Waveland State Historic Site and Kentucky Vietnam Veterans Memorial. Step off the beaten path and head to Creation Museum and The Aviation Museum of Kentucky. Explore the numerous day-trip ideas around Georgetown: Talon Winery & Vineyards (in Lexington) and Ark Encounter (in Williamstown). There's still lots to do: explore the different monuments and memorials at Lexington Cemetery, relax in the rural setting at Old Friends at Dream Chase Farm, see the interesting displays at Ashland: The Henry Clay Estate, and appreciate the extensive heritage of McConnell Springs.

To find more things to do and other tourist information, refer to the Georgetown trip itinerary planner.

Traveling by car from Berea to Georgetown takes an hour. October in Georgetown sees daily highs of 70°F and lows of 49°F at night. Wrap up your sightseeing by early afternoon on the 25th (Thu) to allow enough time to travel back home.

Things to do in Georgetown

Museums Parks Historic Sites

Side Trips

Lexington, Frankfort, Creation Museum, Ark Encounter
Highlights from your plan
Old Friends at Dream Chase Farm ©
Old Friends at Dream Chase Farm
Ark Encounter
Ark Encounter
Ashland: The Henry Clay Estate ©
Ashland: The Henry Clay Estate

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