60 days in Kentucky Itinerary

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 Santa's Candy Castle. Explore Owensboro's surroundings by going to Farmer and Frenchman Winery (in Henderson), Rivertown Trail (in Newburgh) and Evansville (Wesselman Woods Nature Center, USS LST Ship Memorial, &more). There's still lots to do: get in on the family fun at Holiday World & Splashin' Safari, contemplate in the serene atmosphere at Monastery Immaculate conception, relax in the rural setting at Reid's Orchard, and walk around Yellow Creek Park.

Start your trip to Owensboro by creating a personalized itinerary on Inspirock.

Louisville to Owensboro is an approximately 2-hour car ride. You can also drive. The time zone difference when traveling from Louisville to Owensboro is minus 1 hour. In June, plan for daily highs up to 85°F, and evening lows to 67°F. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Paducah.

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Explore hidden gems such as Bob Noble Park and River Discovery Center. Change things up with these side-trips from Paducah: Boo Rochman Memorial Park (in Carbondale), Marion (Rent One Park & Crab Orchard National Wildlife Refuge) and Pomona Natural Bridge (in Pomona). And it doesn't end there: head outdoors with Shawnee Bluffs Canopy Tour, explore the activities along Kentucky Lake, make a trip to Floodwall Murals, and pause for some serene contemplation at St. Francis de Sales Catholic Church.

To find photos, more things to do, reviews, and more tourist information, go to the Paducah trip itinerary builder tool.

Use the Route module to find suitable travel options from Owensboro to Paducah. Expect a daytime high around 87°F in June, and nighttime lows around 67°F. Wrap up your sightseeing on the 10th (Fri) early enough to drive to Hopkinsville.

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 MB Roland Distillery. You'll find plenty of places to visit near Hopkinsville: Paris Landing State Park (in Buchanan), Fort Donelson National Battlefield (in Dover) and Lake Barkley Marina (in Cadiz). And it doesn't end there: stroll around Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium, discover the deep blue sea with Pennyroyal Scuba Blue Springs Resort, steep yourself in history at Jefferson Davis State Historic Site, and cool off at Tie Breaker Family Aquatic Center.

For reviews, photos, traveler tips, and more tourist information, read our Hopkinsville journey app.

You can drive from Paducah to Hopkinsville in 1.5 hours. In June, plan for daily highs up to 85°F, and evening lows to 67°F. Finish your sightseeing early on the 15th (Wed) to allow enough time to drive to Bowling Green.

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 Cub Run Cave. You'll find plenty of places to visit near Bowling Green: Mammoth Cave National Park (Fat Man's Misery, Tall Man's Misery, &more), Nolin Lake State Park (in Mammoth Cave) and Horse Cave (Mammoth Cave Campground, Hidden River Cave and American Cave Museum, &more). There's lots more to do: walk around Fountain Square Park, explore the fascinating underground world of Diamond Caverns, take an in-depth tour of Aviation Heritage Park, and take in the dramatic natural features at Lost River Cave.

To see photos, maps, where to stay, and other tourist information, read Bowling Green trip planning website.

You can drive from Hopkinsville to Bowling Green in 1.5 hours. In June, daytime highs in Bowling Green are 87°F, while nighttime lows are 66°F. Cap off your sightseeing on the 24th (Fri) early enough to go by car to Middlesboro.

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 Yahoo Falls. Get out of town with these interesting Middlesboro side-trips: Split Bow Arch (in Stearns), Oneida (Charit Creek & Twin Arches) and Laurel River Lake (in Williamsburg). There's still lots to do: delve into the lush surroundings at Daniel Boone National Forest, take an in-depth tour of Harland Sanders Cafe And Museum, take in the pleasant sights at Chained Rock, and relax in the rural setting at Mountain Hollow Farm.

To see maps, other places to visit, reviews, and more tourist information, read our Middlesboro trip itinerary maker.

The Route module can help you plan travel from Bowling Green to Middlesboro. In June in Middlesboro, expect temperatures between 84°F during the day and 62°F at night. Cap off your sightseeing on the 27th (Mon) early enough to go by car to Lexington.

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 James E. Pepper Distillery and Unique Horse Farm Tours. Explore Lexington's surroundings by going to Versailles (Sun Valley Farm & Woodford Reserve Distillery), Frankfort (New Capitol Building, Liberty Hall Historic Site, &more) and Cincinnati (Cathedral Basilica of St. Peter in Chains, Cincinnati Reds Hall of Fame & Museum, &more). And it doesn't end there: see the interesting displays at Aviation Museum of Kentucky, experience rural life at Mill Ridge Farm, learn insider's secrets on a distillery tour, and appreciate the extensive heritage of Waveland State Historic Site.

To see traveler tips, where to stay, ratings, and tourist information, read our Lexington day trip planning app.

The Route module can help you plan travel from Middlesboro to Lexington. Due to the time zone difference, you'll lose 1 hour traveling from Middlesboro to Lexington. In June in Lexington, expect temperatures between 84°F during the day and 64°F at night. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Louisville.

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 Locust Grove. Change things up with these side-trips from Louisville: Corydon (Indiana Caverns & Battle of Corydon Battlefield), Squire Boone Caverns (in Mauckport) and Indianapolis (Indiana War Memorial, Rhythm! Discovery Center, &more). And it doesn't end there: explore the different monuments and memorials at Cave Hill Cemetery, explore the fascinating underground world of Marengo Cave, go on a hair-raising tour with a ghost and vampire tour, and walk around The Parklands of Floyds Fork.

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.