44 days in Kentucky Itinerary

44 days in Kentucky Itinerary

Created using Inspirock Kentucky tour planner

Make it your trip
Fly
1
Paducah
— 3 nights
Drive
2
Park City
— 2 nights
Drive
3
Louisville
— 4 nights
Drive
4
Middlesboro
— 1 night
Drive
5
Lexington
— 4 nights
Drive
6
Frankfort
— 3 nights
Drive
7
Bowling Green
— 3 nights
Drive
8
Danville
— 3 nights
Drive
9
Elizabethtown
— 3 nights
Drive
10
Berea
— 3 nights
Drive
11
Versailles
— 3 nights
Drive
12
Lawrenceburg
— 3 nights
Drive
13
Bardstown
— 3 nights
Drive
14
Harrodsburg
— 3 nights
Drive
15
Hopkinsville
— 2 nights
+2
Drive to Lawrenceville Vincennes International Airport, Fly to Logan International Airport, Drive to Boston

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Paducah

— 3 nights
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Your day by day itinerary now includes Southern Illinois Art and Artisans Center, Historic Downtown Sikeston, U.S. Custom House, and other attractions you added. Give yourself a bit of retail therapy at Hancock's of Paducah and Yeiser Art Center. Museum-lovers will get to explore River Discovery Center and The PAPA Gallery. Explore Paducah's surroundings by going to Surrender House - Dover Hotel (in Dover) and Cobden (Lincoln Heritage Winery & StarView Vineyards). There's lots more to do: contemplate the long history of William Clark Market House Museum, admire the masterpieces at The National Quilt Museum, make a trip to Floodwall Murals, and sample the fine beverages at The Moonshine Company.

To see traveler tips, maps, and other tourist information, refer to the Paducah online trip builder.

Boston to Paducah is an approximately 7-hour flight. You can also drive; or take a bus. Traveling from Boston to Paducah, you'll gain 1 hour due to the time zone difference. Expect somewhat warmer weather when traveling from Boston in December: highs in Paducah hover around 49°F, while lows dip to 32°F. Finish your sightseeing early on the 24th (Tue) so you can travel to Park City.

Things to do in Paducah

Museums · Historic Sites · Parks · Nature

Side Trips

Park City

— 2 nights
Park City is a home rule-class city in Barren County, Kentucky, United States. Kick off your visit on the 25th (Wed): take an in-depth tour of South Central Kentucky Cultural Center, browse the collection at The Book Store, then stroll through Cedar Sink Trail, and finally steep yourself in history at Fort Williams. Get ready for a full day of sightseeing on the 26th (Thu): Head underground at Mammoth Cave Campground, stop by Detweiler's Country Store, and then immerse yourself in nature at Nolin Lake State Park.

To see photos, traveler tips, where to stay, and more tourist information, refer to the Park City trip builder website.

Drive from Paducah to Park City in 3 hours. December in Park City sees daily highs of 49°F and lows of 32°F at night. Wrap up your sightseeing on the 26th (Thu) to allow time to travel to Louisville.

Things to do in Park City

Parks · Nature · Outdoors · Trails

Side Trips

Louisville

— 4 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You've added Santa Claus Land of Lights, Bear Wallow Distillery, Dubois County Museum, and other attractions to your itinerary. Conrad-Caldwell House Museum (Conrad's Castle) and The Speed Art Museum will appeal to museum buffs. Do your shopping at 21c Museum Hotel and Art Eatables. Explore Louisville's surroundings by going to Spring Mill State Park (in Mitchell), Lincoln Boyhood National Memorial (in Lincoln City) and Monastery Immaculate conception (in Ferdinand). There's still lots to do: brush up on your knowledge of spirits at Kentucky Artisan Distillery, stroll around The Parklands of Floyds Fork, and get thoroughly spooked out with Old Louisville.

To see other places to visit, more things to do, photos, and more tourist information, use the Louisville trip itinerary planner.

Traveling by car from Park City to Louisville takes 1.5 hours. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect a daytime high around 48°F in December, and nighttime lows around 33°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to travel to Middlesboro.

Things to do in Louisville

Museums · Historic Sites · Parks · Nature

Side Trips

Middlesboro

— 1 night
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Kick off your visit on the 31st (Tue): hike along Tri State Peak Trail, take an in-depth tour of Abraham Lincoln Library and Museum, and then see the interesting displays at Little Congress Bicycle Museum.

For where to stay, photos, ratings, and tourist information, go to the Middlesboro trip builder site.

Traveling by car from Louisville to Middlesboro takes 3.5 hours. Traveling from Louisville to Middlesboro, you'll gain 1 hour due to the time zone difference. In December, daily temperatures in Middlesboro can reach 50°F, while at night they dip to 32°F. Wrap up your sightseeing on the 31st (Tue) to allow time to travel to Lexington.

Things to do in Middlesboro

Parks · Outdoors · Trails · Museums

Side Trips

Lexington

— 4 nights

Horse Capital of the World

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Your day by day itinerary now includes Kentucky Scenic Byway, Mary Todd Lincoln House and University of Kentucky Art Museum. Get outdoors at Legacy Trail and Kentucky Horse Park. Your inner history buff will appreciate Lexington Cemetery and John Rankin House. Explore Lexington's surroundings by going to Carter Caves State Resort Park (in Olive Hill) and Kentucky Gateway Museum Center (in Maysville). Next up on the itinerary: relax and rejuvenate at some of the best spas, examine the collection at Headley-Whitney Museum, brush up on your knowledge of spirits at Bluegrass Distillers, and look for all kinds of wild species at Raven Run Nature Sanctuary.

For where to stay, ratings, traveler tips, and other tourist information, use the Lexington online vacation maker.

Traveling by car from Middlesboro to Lexington takes 2.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Middlesboro to Lexington. December in Lexington sees daily highs of 48°F and lows of 32°F at night. Wrap up your sightseeing on the 4th (Sat) early enough to drive to Frankfort.

Things to do in Lexington

Parks · Museums · Nature · Historic Sites

Side Trips

Frankfort

— 3 nights
Frankfort is the capital city of the Commonwealth of Kentucky and the seat of Franklin County. You've added Kentucky Military History Museum, Rebecca Ruth Candy Tours & Museum, Three Boys Farm Distillery, and other attractions to your itinerary. On the 5th (Sun), stroll the grounds of Kentucky Vietnam Veterans Memorial, brush up on your knowledge of spirits at Buffalo Trace Distillery, sample the fine beverages at Glenns Creek Distillery, sample the fine beverages at Three Boys Farm Distillery, then examine the collection at Rebecca Ruth Candy Tours & Museum, and finally learn about all things military at Kentucky Military History Museum. Keep things going the next day: examine the collection at Capital City Museum, explore the different monuments and memorials at Frankfort Cemetery, then do a tasting at The Ridge Winery Tasting Room, and finally buy something for everyone on your list at Ghirardelli Chocolate Outlet and Ice Cream Shop.

For ratings, reviews, more things to do, and tourist information, refer to the Frankfort trip tool.

Traveling by car from Lexington to Frankfort takes an hour. Alternatively, you can take a bus. In January, daytime highs in Frankfort are 41°F, while nighttime lows are 23°F. Wrap up your sightseeing by early afternoon on the 7th (Tue) to allow enough time to drive to Bowling Green.

Things to do in Frankfort

Museums · Historic Sites · Breweries & Distilleries · Shopping

Side Trips

Bowling Green

— 3 nights
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Bill Monroe's Home Place and Riverview at Hobson Grove will appeal to history buffs. Step off the beaten path and head to South Union Shaker Village and Sumner Crest WInery. Change things up with these side-trips from Bowling Green: Habbeger's Amish Market (in Scottsville), Farmer Brown's Produce & General Store (in Gallatin) and Cragfont State Historic Site (in Castalian Springs). And it doesn't end there: get engrossed in the history at The Kentucky Museum, pick up a one of a kind souvenir at Bright's Antique World, take in the spiritual surroundings of St. Joseph Catholic Church, and bet on your favorite at NCM Motorsports Park.

For maps, reviews, traveler tips, and tourist information, refer to the Bowling Green road trip website.

Traveling by car from Frankfort to Bowling Green takes 3 hours. Alternatively, you can take a bus; or take a bus. Traveling from Frankfort to Bowling Green, you'll gain 1 hour due to the time zone difference. January in Bowling Green sees daily highs of 45°F and lows of 26°F at night. Wrap up your sightseeing on the 10th (Fri) early enough to travel to Danville.

Things to do in Bowling Green

Historic Sites · Museums · Shopping · Nature

Side Trips

Danville

— 3 nights
Danville is a home rule-class city in Boyle County, Kentucky, in the United States. Start off your visit on the 11th (Sat): witness the site of a historic battle at Millsprings Battlefield Museum, then do a tasting at Cave Hill Vineyard & Winery, then see the interesting displays at The Great American Dollhouse Museum, and finally get behind the scenes at Kentucky Soaps and Such. Here are some ideas for day two: contemplate the waterfront views at Lake Cumberland State Resort Park and then identify plant and animal life at Cumberland Point Recreational Area.

To find more things to do, photos, maps, and tourist information, you can read our Danville day trip site.

Drive from Bowling Green to Danville in 2.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Bowling Green to Danville. In January, daily temperatures in Danville can reach 41°F, while at night they dip to 23°F. Wrap up your sightseeing by early afternoon on the 13th (Mon) to allow time for the car ride to Elizabethtown.

Things to do in Danville

Parks · Museums · Nature · Wildlife

Side Trips

Elizabethtown

— 3 nights
Elizabethtown is a home rule-class city and the county seat of Hardin County, Kentucky, in the United States. Swope's Cars of Yesteryear Museum and Brown-Pusey House will appeal to museum buffs. Visit Abraham Lincoln Birthplace National Historical Park and Elizabethtown City Cemetery for their historical value. Explore the numerous day-trip ideas around Elizabethtown: Rockport (Lincoln Pioneer Village & Museum & Pepper's Ridge Winery), Blue Heron Vineyard & Winery (in Cannelton) and Otter Creek Outdoor Recreation Area (in Brandenburg). Next up on the itinerary: pick up a one of a kind souvenir at The Glendale Antique Mall, brush up on your knowledge of spirits at Boundary Oak Distillery, and make a trip to Kentucky September 11th Memorial.

For photos, maps, ratings, and more tourist information, refer to the Elizabethtown trip itinerary builder app.

You can drive from Danville to Elizabethtown in 1.5 hours. In January, daily temperatures in Elizabethtown can reach 41°F, while at night they dip to 23°F. Wrap up your sightseeing on the 16th (Thu) to allow time to travel to Berea.

Things to do in Elizabethtown

Museums · Wineries · Historic Sites · Wildlife

Side Trips

Berea

— 3 nights
Berea is a home rule-class city in Madison County, Kentucky, in the United States. Your list of things to see and do now includes Berea Cemetery, Old Town Fudge Factory, Todd's Antique Mall, and other attractions. On the 17th (Fri), stroll the grounds of Berea Cemetery, stop by Log House Craft Gallery, look for gifts at Old Town Fudge Factory, take a stroll through Artisan Village District, then buy something for everyone on your list at Todd's Antique Mall, and finally steep yourself in history at Fitchburg Furnace. Get ready for a full day of sightseeing on the next day: take in the exciting artwork at Berea Arts Council, see the interesting displays at Kentucky Music Hall of Fame, then steep yourself in history at William Whitley House, and finally learn about winemaking at Cedar Creek Vineyards.

For ratings, other places to visit, photos, and more tourist information, go to the Berea online trip itinerary builder.

Getting from Elizabethtown to Berea by car takes about 2.5 hours. In January, daytime highs in Berea are 40°F, while nighttime lows are 23°F. On the 19th (Sun), wrap the sightseeing up by early afternoon so you can drive to Versailles.

Things to do in Berea

Museums · Shopping · Historic Sites · Neighborhoods

Side Trips

Versailles

— 3 nights
Versailles is a home rule-class city in Woodford County, Kentucky, United States and is located near Lexington. Deepen your sense of the past at sights like The Castle and Jack Jouett House Historic Site. Shop till you drop at Downtown Midway Kentucky and Irish Acres Gallery of Antiques. There's much more to do: identify plant and animal life at Coolmore America - Ashford Stud, relax in the rural setting at Old Friends at Dream Chase Farm, explore and take pictures at Old Frankfort Pike, and do a tasting at Equus Run Vineyard & Winery.

To see reviews, other places to visit, more things to do, and tourist information, read our Versailles trip itinerary planning tool.

You can drive from Berea to Versailles in an hour. January in Versailles sees daily highs of 41°F and lows of 24°F at night. Wrap up your sightseeing on the 22nd (Wed) early enough to drive to Lawrenceburg.

Things to do in Versailles

Shopping · Scenic Drive · Outdoors · Wineries

Side Trips

Lawrenceburg

— 3 nights
Lawrenceburg is a home rule-class city in Anderson County, Kentucky, United States. Kick off your visit on the 23rd (Thu): sample the fine beverages at Wild Turkey Distillery, then take in the exciting artwork at Elements Clay Studio and Stuff, then brush up on your knowledge of spirits at Four Roses Bourbon - Warehouse and Bottling Facility, and finally sample the fine beverages at Four Roses. On the 24th (Fri), you'll have a packed day of sightseeing: learn about winemaking at Lovers Leap Vineyards and Winery.

To see reviews, ratings, more things to do, and other tourist information, refer to the Lawrenceburg itinerary builder site.

Lawrenceburg is very close to Versailles. In January in Lawrenceburg, expect temperatures between 41°F during the day and 23°F at night. You will leave for Bardstown on the 25th (Sat).

Things to do in Lawrenceburg

Breweries & Distilleries · Wineries · Museums · Shopping

Side Trip

Bardstown

— 3 nights
Bardstown is a home rule-class city in Nelson County, Kentucky, in the United States. Get some cultural insight at My Old Kentucky Home and Springhill Winery. Eschew the tourist crowds and head to The Abbey of Gethsemani and Spalding Hall. Get out of town with these interesting Bardstown side-trips: Limestone Branch Distillery (in Lebanon) and Campbellsville (Atkinson-Griffin Log House-Confederate Hospital & Green River Lake State Park). And it doesn't end there: do a tasting at McIntyre's Winery & Berries, brush up on your knowledge of spirits at Preservation Distillery, take in the exciting artwork at Bardstown Art Gallery, and stop by The Blind Pig Bourbon Market.

To find traveler tips, more things to do, where to stay, and other tourist information, refer to the Bardstown travel planning tool.

Traveling by car from Lawrenceburg to Bardstown takes an hour. In January, daytime highs in Bardstown are 41°F, while nighttime lows are 23°F. Finish your sightseeing early on the 28th (Tue) to allow enough time to drive to Harrodsburg.

Things to do in Bardstown

Wineries · Museums · Historic Sites · Nature

Side Trips

Harrodsburg

— 3 nights
Harrodsburg is a home rule-class city in Mercer County, Kentucky, in the United States. Kick off your visit on the 29th (Wed): contemplate the long history of Shaker Village of Pleasant Hill, then contemplate the long history of Old Fort Harrod State Park, then learn about winemaking at Horseshoe Bend Vineyards and WineryHorseshoe Bend Vineyards and Winery, and finally witness the site of a historic battle at Perryville Battlefield State Historic Site.

To find where to stay, more things to do, ratings, and tourist information, you can read our Harrodsburg road trip tool.

You can drive from Bardstown to Harrodsburg in an hour. In January, daytime highs in Harrodsburg are 41°F, while nighttime lows are 23°F. You will leave for Hopkinsville on the 31st (Fri).

Things to do in Harrodsburg

Historic Sites · Wineries

Side Trips

Hopkinsville

— 2 nights
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Kick off your visit on the 31st (Fri): brush up on your knowledge of spirits at Casey Jones Distillery. Here are some ideas for day two: look for gifts at Griffin's Studio, then see the interesting displays at Robert Penn Warren Birthplace Museum, and then take in the history at Fort Donelson National Battlefield.

For reviews, other places to visit, where to stay, and other tourist information, use the Hopkinsville trip itinerary planner.

Getting from Harrodsburg to Hopkinsville by car takes about 3.5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Harrodsburg to Hopkinsville. In January, plan for daily highs up to 44°F, and evening lows to 27°F. You will have some time to spend on the 2nd (Sun) before leaving for home.

Things to do in Hopkinsville

Historic Sites · Nature · Parks · Museums

Side Trips

Kentucky travel guide

4.5
Caves · Specialty Museums · Distilleries
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.