60 days in Kentucky Itinerary

60 days in Kentucky Itinerary

Created using Inspirock Kentucky journey planner
Make it your trip
Drive
1
Owensboro
— 4 nights
Drive
2
Paducah
— 5 nights
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3
Hopkinsville
— 5 nights
Drive
4
Bowling Green
— 9 nights
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5
Middlesboro
— 3 nights
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6
Lexington
— 14 nights
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7
Louisville
— 19 nights

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Owensboro — 4 nights

Owensboro is a home rule-class city in and the county seat of Daviess County, Kentucky, United States. Discover out-of-the-way places like Smothers Park and USS LST Ship Memorial. Explore Owensboro's surroundings by going to Farmer and Frenchman Winery (in Henderson), Rivertown Trail (in Newburgh) and Evansville (Wesselman Woods Nature Center, Evansville Wartime Museum, &more). There's lots more to do: get in on the family fun at Santa's Candy Castle, contemplate in the serene atmosphere at Saint Meinrad Archabbey, appreciate the history behind 1935 Santa Statue, and stroll around Panther Creek Park.

To find photos, where to stay, reviews, and other tourist information, read Owensboro trip planning tool.

Louisville to Owensboro is an approximately 2-hour car ride. You'll gain 1 hour traveling from Louisville to Owensboro due to the time zone difference. In June in Owensboro, expect temperatures between 85°F during the day and 67°F at night. Finish your sightseeing early on the 5th (Sun) so you can travel to Paducah.
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Parks · Museums · Historic Sites · Wildlife
Side Trips

Paducah — 5 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Explore hidden gems such as Floodwall Murals and The National Quilt Museum. Change things up with these side-trips from Paducah: Marion (Rent One Park & Crab Orchard National Wildlife Refuge), Boo Rochman Memorial Park (in Carbondale) and Pomona Natural Bridge (in Pomona). Next up on the itinerary: walk around Bob Noble Park, see human ingenuity at work at Kentucky Dam, pause for some photo ops at Wacinton Sculpture, and cool off at Venture River Water Park.

To find where to stay, ratings, reviews, and other tourist information, refer to the Paducah visit planning app.

Drive from Owensboro to Paducah in 2.5 hours. In June, daily temperatures in Paducah can reach 87°F, while at night they dip to 67°F. Wrap up your sightseeing on the 10th (Fri) to allow time to drive to Hopkinsville.
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Parks · Outdoors · Museums · Wildlife
Side Trips

Hopkinsville — 5 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Explore hidden gems such as Casey Jones Distillery and Trail of Tears Commemorative Park and Heritage Center. You'll find plenty of places to visit near Hopkinsville: Paris Landing State Park (in Buchanan), Lake Barkley Marina (in Cadiz) and Fort Donelson National Battlefield (in Dover). Next up on the itinerary: walk around Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium, see some colorful creatures with Pennyroyal Scuba Blue Springs Resort, indulge your thirst for a good beer at Hopkinsville Brewing Company, and make a trip to Ruby Laffoon Log Cabin.

To see more things to do, ratings, other places to visit, and other tourist information, read Hopkinsville trip planning app.

Getting from Paducah to Hopkinsville by car takes about 1.5 hours. In June in Hopkinsville, expect temperatures between 85°F during the day and 67°F at night. Cap off your sightseeing on the 15th (Wed) early enough to go by car to Bowling Green.
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Parks · Nature · Museums · Wildlife
Side Trips

Bowling Green — 9 nights

Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. You'll explore the less-touristy side of things at Chaney's Dairy Barn and Aviation Heritage Park. You'll find plenty of places to visit near Bowling Green: Mammoth Cave National Park (Fat Man's Misery, Tall Man's Misery, &more), Horse Cave (Mammoth Cave Campground, Hidden River Cave and American Cave Museum, &more) and Nolin Lake State Park (in Mammoth Cave). There's much more to do: stroll around Fountain Square Park, Head underground at Diamond Caverns, gain insight at Western Kentucky University, and examine the collection at National Corvette Museum.

For more things to do, maps, photos, and other tourist information, refer to the Bowling Green trip planner.

You can drive from Hopkinsville to Bowling Green in 1.5 hours. In June, plan for daily highs up to 87°F, and evening lows to 66°F. Finish your sightseeing early on the 24th (Fri) to allow enough time to travel to Middlesboro.
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Parks · Nature · Outdoors · Museums
Side Trips

Middlesboro — 3 nights

Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Eschew the tourist crowds and head to Cumberland Gap National Historical Park and Charit Creek. Get out of town with these interesting Middlesboro side-trips: Twin Arches (in Oneida), Yahoo Falls (in Whitley City) and Split Bow Arch (in Stearns). There's much more to do: take an in-depth tour of Harland Sanders Cafe And Museum, take in the pleasant sights at Chained Rock, take a peaceful walk through Daniel Boone National Forest, and hike along Tri State Peak Trail.

To find other places to visit, photos, reviews, and more tourist information, read our Middlesboro trip itinerary planning website.

Traveling by car from Bowling Green to Middlesboro takes 3.5 hours. In June, plan for daily highs up to 84°F, and evening lows to 62°F. Wrap up your sightseeing on the 27th (Mon) early enough to travel to Lexington.
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Parks · Nature · Outdoors · Trails
Side Trips

Lexington — 14 nights

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Explore hidden gems such as Aviation Museum of Kentucky and Mary Todd Lincoln House. Explore Lexington's surroundings by going to Frankfort (New Capitol Building, Liberty Hall Historic Site, &more), Versailles (Sun Valley Farm & Woodford Reserve Distillery) and Cincinnati (Cathedral Basilica of St. Peter in Chains, Cincinnati Reds Hall of Fame & Museum, &more). Next up on the itinerary: surround yourself with nature on Unique Horse Farm Tours, don't miss a visit to The Thoroughbred Center, stroll the grounds of Lexington Cemetery, and test your problem-solving skills at popular escape rooms.

Ask Inspirock to suggest an itinerary and make planning a trip to Lexington fast, fun, and easy.

You can drive from Middlesboro to Lexington in 2.5 hours. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. June in Lexington sees daily highs of 84°F and lows of 64°F at night. Finish up your sightseeing early on the 11th (Mon) so you can go by car to Louisville.
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Parks · Historic Sites · Breweries & Distilleries · Museums
Side Trips

Louisville — 19 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You'll discover tucked-away gems like Conrad-Caldwell House Museum (Conrad's Castle) and Marengo Cave. Change things up with these side-trips from Louisville: Indianapolis (Indiana War Memorial, Rhythm! Discovery Center, &more), Corydon (Indiana Caverns & Battle of Corydon Battlefield) and Squire Boone Caverns (in Mauckport). And it doesn't end there: Head underground at Louisville Mega Cavern, stroll around The Parklands of Floyds Fork, brush up on your knowledge of spirits at Copper & Kings American Brandy Distillery, and see the interesting displays at Muhammad Ali Center.

For ratings, maps, and tourist information, refer to the Louisville route tool.

Getting from Lexington to Louisville by car takes about 1.5 hours. Other options: take a bus. In July, plan for daily highs up to 87°F, and evening lows to 69°F. Finish up your sightseeing early on the 30th (Sat) so you can travel back home.
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Parks · Historic Sites · Museums · Breweries & Distilleries
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.
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