60 days in Kentucky Itinerary

60 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner
Make it your trip
Fly
1
Louisville
— 14 nights
Drive
2
Owensboro
— 6 nights
Drive
3
Paducah
— 7 nights
Drive
4
Hopkinsville
— 6 nights
Drive
5
Bowling Green
— 7 nights
Drive
6
Lebanon
— 2 nights
Drive
7
Lexington
— 13 nights
Drive
8
Petersburg
— 2 nights
Drive to Cincinnati Northern Kentucky International Airport, Fly to Brisbane

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Louisville — 14 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Explore the numerous day-trip ideas around Louisville: James B. Beam Distilling Co. (in Clermont), Bardstown (Barton 1792 Distillery, Willett Distilling Company, &more) and Forest Edge Winery (in Shepherdsville). The adventure continues: explore the fascinating underground world of Louisville Mega Cavern, see the interesting displays at Swope's Cars of Yesteryear Museum, try to win big at Churchill Downs, and steep yourself in history at Conrad-Caldwell House Museum (Conrad's Castle).

For reviews, maps, other places to visit, and other tourist information, use the Louisville travel route website.

Brisbane, Australia to Louisville is an approximately 24-hour flight. You'll gain 15 hours traveling from Brisbane to Louisville due to the time zone difference. Expect a bit warmer temperatures when traveling from Brisbane in September; daily highs in Louisville reach 32°C and lows reach 19°C. Finish your sightseeing early on the 1st (Sat) so you can travel to Owensboro.
Breweries & Distilleries · Museums · Historic Sites · Parks
Side Trips

Owensboro — 6 nights

Owensboro is a home rule-class city in and the county seat of Daviess County, Kentucky, United States. Change things up with these side-trips from Owensboro: Henderson (Ruby Moon Vineyard & Winery & Farmer and Frenchman Winery), Bill Monroe's Home Place (in Rosine) and Everly Brothers Monument (in Central City). There's still lots to do: walk around Smothers Park, hunt for treasures at Preservation Station Market And Event Center, brush up on your knowledge of spirits at O.Z. Tyler Distillery, and relax in the rural setting at Reid's Orchard.

For where to stay and more tourist information, go to the Owensboro day trip planning app.

Traveling by car from Louisville to Owensboro takes 2 hours. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Expect a daytime high around 25°C in October, and nighttime lows around 11°C. Cap off your sightseeing on the 7th (Fri) early enough to travel to Paducah.
Parks · Wineries · Breweries & Distilleries · Historic Sites
Side Trips

Paducah — 7 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Change things up with these side-trips from Paducah: Kentucky Lake (in Gilbertsville), Fort Jefferson Memorial Cross (in Wickliffe) and Columbus-Belmont State Park (in Columbus). And it doesn't end there: explore the world behind art at The National Quilt Museum, see the interesting displays at River Discovery Center, make a trip to Floodwall Murals, and do a tasting at Purple Toad Winery.

To see where to stay, reviews, more things to do, and other tourist information, refer to the Paducah trip builder site.

Traveling by car from Owensboro to Paducah takes 2.5 hours. In October, daytime highs in Paducah are 26°C, while nighttime lows are 11°C. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Hopkinsville.
Parks · Museums · Historic Sites · Nature
Side Trips

Hopkinsville — 6 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Explore the numerous day-trip ideas around Hopkinsville: Adsmore House & Gardens (in Princeton), Trover Wellness Park (in Madisonville) and Golden Pond (Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium & The Elk and Bison Prairie). Next up on the itinerary: sample the fine beverages at Casey Jones Distillery, see the interesting displays at Robert Penn Warren Birthplace Museum, stop by Griffin's Studio, and get a new perspective on things with Pennyroyal Scuba Blue Springs Resort.

For other places to visit, where to stay, and other tourist information, read Hopkinsville trip planner.

You can drive from Paducah to Hopkinsville in 1.5 hours. In October in Hopkinsville, expect temperatures between 26°C during the day and 12°C at night. Finish up your sightseeing early on the 20th (Thu) so you can go by car to Bowling Green.
Parks · Wildlife · Breweries & Distilleries · Museums
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: Mammoth Cave National Park (Nature & Wildlife Tours, Fat Man's Misery, &more) and Kentucky Down Under Adventure Zoo (in Horse Cave). There's much more to do: examine the collection at National Corvette Museum, experience rural life at Chaney's Dairy Barn, take an in-depth tour of South Union Shaker Village, and contemplate in the serene atmosphere at St. Joseph Catholic Church.

To see photos, other places to visit, and more tourist information, you can read our Bowling Green trip builder tool.

Traveling by car from Hopkinsville to Bowling Green takes 1.5 hours. Expect a daytime high around 26°C in October, and nighttime lows around 11°C. Wrap up your sightseeing on the 27th (Thu) to allow time to travel to Lebanon.
Parks · Outdoors · Nature · Trails
Side Trips

Lebanon — 2 nights

Lebanon is a home rule-class city in Marion County, Kentucky, in the United States. Kick off your visit on the 28th (Fri): sample the fine beverages at Wilderness Trail Distillery, then don't miss a visit to Constitution Square Historic Site, and then examine the collection at The Great American Dollhouse Museum. On the next day, brush up on your knowledge of spirits at Maker's Mark and then sample the fine beverages at Limestone Branch Distillery.

To find more things to do, photos, reviews, and other tourist information, go to the Lebanon journey builder website.

Traveling by car from Bowling Green to Lebanon takes 2 hours. The time zone difference when traveling from Bowling Green to Lebanon is 1 hour. Traveling from Bowling Green in October, you will find days in Lebanon are a bit cooler (23°C), and nights are about the same (9°C). Cap off your sightseeing on the 29th (Sat) early enough to go by car to Lexington.
Breweries & Distilleries · Museums
Side Trips

Lexington — 13 nights

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Explore Lexington's surroundings by going to Frankfort (Kentucky Vietnam Veterans Memorial, Castle & Key Distillery, &more), Boone County Distilling Co. (in Independence) and Ark Encounter (in Williamstown). Next up on the itinerary: surround yourself with nature on Unique Horse Farm Tours, experience rural life at Sun Valley Farm, sample the tasty concoctions at West Sixth Brewing, and gain some tasty knowledge on a distillery tour.

To see reviews, maps, where to stay, and more tourist information, read our Lexington route planning site.

Traveling by car from Lebanon to Lexington takes 1.5 hours. Expect a daytime high around 24°C in October, and nighttime lows around 11°C. Finish your sightseeing early on the 11th (Fri) to allow enough time to travel to Petersburg.
Breweries & Distilleries · Historic Sites · Museums · Parks
Side Trips

Petersburg — 2 nights

Located on the site of an ancient Indian settlement, Petersburg is a small rural community.
On the 12th (Sat), head outdoors with England idlewild park, then stroll the grounds of Dinsmore Homestead, and then get a new perspective on nature at Creation Museum. Keep things going the next day: immerse yourself in nature at Big Bone Lick State Historic Site and then learn about winemaking at Verona Vineyards.

To see reviews, ratings, traveler tips, and other tourist information, refer to the Petersburg trip planner.

Traveling by car from Lexington to Petersburg takes 2 hours. In November in Petersburg, expect temperatures between 14°C during the day and 1°C at night. Wrap up your sightseeing on the 13th (Sun) to allow time to travel back home.
Childrens Museums · Museums · Outdoors · Parks
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.