5 days in Kentucky Itinerary

5 days in Kentucky Itinerary

Created using Inspirock Kentucky trip itinerary planner

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Route & dates

5 days in Kentucky Itinerary

Start: Chicago
Fly:  3​h 15​min
1
Williamstown
— Few hours
Drive:  1​h 45​min
2
Berea
— 1 night
Drive:  2​h
3
Louisville
— 2 nights
Drive:  3​h 45​min
4
Paducah
— 1 night
Fly:  3​h 15​min
End: Chicago

few
hours
Williamstown

Williamstown
Williamstown is a home-rule-class city in Grant and Pendleton counties in the U.S. Kick off your visit on the 5th (Fri): get engrossed in the history at Ark Encounter.

To see other places to visit, reviews, and more tourist information, you can read our Williamstown online journey planner .

Chicago to Williamstown is an approximately 3.5-hour combination of flight and taxi. You can also drive; or do a combination of bus and taxi. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In July, daily temperatures in Williamstown can reach 84°F, while at night they dip to 66°F. Finish your sightseeing early on the 5th (Fri) so you can travel to Berea.

Things to do in Williamstown

Museums
Highlights from your plan
Ark Encounter
Ark Encounter

1
night
Berea

Berea ©
Berea is a home rule-class city in Madison County, Kentucky, in the United States. On the 6th (Sat), make a trip to Student Crafts on the Square Gallery, wander the streets of Artisan Village District, view the masterpieces at Berea Arts Council, stop by Weston Glass Studio, then view the masterpieces at Kentucky Artisan Center at Berea, and finally browse for treasures at Todd's Antique Mall.

Before you visit Berea, use our trip planner to discover what you can do and see there.

You can drive from Williamstown to Berea in 1.5 hours. In July, plan for daily highs up to 83°F, and evening lows to 65°F. Finish your sightseeing early on the 6th (Sat) to allow enough time to travel to Louisville.

Things to do in Berea

Shopping Museums Neighborhoods
Highlights from your plan
Kentucky Artisan Center at Berea ©
Weston Glass Studio ©
Weston Glass Studio
Berea Arts Council ©
Berea Arts Council

2
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Start off your visit on the 7th (Sun): explore the world behind art at 21c Museum Hotel, examine the collection at Louisville Slugger Museum & Factory, then see the interesting displays at Kentucky Derby Museum, and finally bet on a winner at Churchill Downs. On the 8th (Mon), you'll have a packed day of sightseeing: take in the exciting artwork at Flame Run Glass Studio and Gallery, sample the fine beverages at Kentucky Peerless Distilling Co, take in the views from The Big Four Bridge, then Head underground at Louisville Mega Cavern, and finally look for gifts at Art Eatables.

To see more things to do, ratings, photos, and tourist information, go to the Louisville trip itinerary planner .

Traveling by car from Berea to Louisville takes 2 hours. Expect a daytime high around 87°F in July, and nighttime lows around 69°F. Wrap up your sightseeing on the 8th (Mon) early enough to drive to Paducah.

Things to do in Louisville

Museums Historic Sites Nature
Highlights from your plan
Churchill Downs ©
Churchill Downs
Louisville Slugger Museum & Factory ©
Kentucky Derby Museum ©
Kentucky Derby Museum

1
night
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Kick off your visit on the 9th (Tue): admire the masterpieces at The National Quilt Museum, view the masterpieces at The PAPA Gallery, stop by Twin Lakes Antique Mall, then learn about winemaking at Purple Toad Winery, and finally don't miss a visit to Floodwall Murals.

To see ratings, traveler tips, other places to visit, and tourist information, read our Paducah trip planner .

You can drive from Louisville to Paducah in 4 hours. Alternatively, you can take a bus; or fly. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In July, daily temperatures in Paducah can reach 88°F, while at night they dip to 69°F. Finish your sightseeing early on the 9th (Tue) to allow enough time to travel back home.

Things to do in Paducah

Museums Shopping Wineries

Side Trip

Twin Lakes Antique Mall
Highlights from your plan
The National Quilt Museum ©
The National Quilt Museum
Purple Toad Winery ©
Purple Toad Winery
Twin Lakes Antique Mall ©
Twin Lakes Antique Mall

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