44 days in Kentucky Itinerary

44 days in Kentucky Itinerary

Created using Inspirock Kentucky tour planner

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Route & dates

44 days in Kentucky Itinerary

Start: Boston
Fly:  6​h 30​min
1
Paducah
— 3 nights
Drive:  3​h
2
Park City
— 2 nights
Drive:  2​h
3
Louisville
— 4 nights
Drive:  3​h 30​min
4
Middlesboro
— 1 night
Drive:  2​h 30​min
5
Lexington
— 4 nights
Drive:  45​min
6
Frankfort
— 3 nights
Drive:  2​h 45​min
7
Bowling Green
— 3 nights
Drive:  2​h 15​min
8
Danville
— 3 nights
Drive:  1​h 30​min
9
Elizabethtown
— 3 nights
Drive:  2​h
10
Berea
— 3 nights
Drive:  1​h
11
Versailles
— 3 nights
Drive:  15​min
12
Lawrenceburg
— 3 nights
Drive:  45​min
13
Bardstown
— 3 nights
Drive:  1​h
14
Harrodsburg
— 3 nights
Drive:  3​h 15​min
15
Hopkinsville
— 2 nights
Drive + Fly:  9​h 15​min
End: Boston

3
nights
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Your list of things to see and do now includes Southern Illinois Art and Artisans Center, Historic Downtown Sikeston, U.S. Custom House, and other attractions. Explore hidden gems such as River Discovery Center and William Clark Market House Museum. Your cultural itinerary includes sights like StarView Vineyards and The National Quilt Museum. Change things up with these side-trips from Paducah: Surrender House - Dover Hotel (in Dover) and Lincoln Heritage Winery (in Cobden). There's still lots to do: examine the collection at Paducah Distilled Spirits, see human ingenuity at work at Kentucky Dam, pause for some serene contemplation at St. Francis de Sales Catholic Church, and brush up on your knowledge of spirits at The Moonshine Company.

For photos, more things to do, where to stay, and more tourist information, use the Paducah online itinerary planner .

Boston to Paducah is an approximately 6.5-hour flight. You can also do a combination of flight and car; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Boston to Paducah. When traveling from Boston in December, plan for a bit warmer days in Paducah, with highs around 49°F, while nights are about the same with lows around 32°F. Finish up your sightseeing early on the 24th (Tue) so you can travel to Park City.

Things to do in Paducah

Museums Historic Sites Parks

Side Trips

Dover, Metropolis, Cobden, Shawnee Bluffs Canopy Tour, Stars and Stripes Museum
Highlights from your plan
Fort Donelson National Battlefield ©
StarView Vineyards ©
StarView Vineyards

2
nights
Park City

Park City ©
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, get lost in a book at The Book Store, then trek along Cedar Sink Trail, and finally contemplate the long history of Fort Williams. Get ready for a full day of sightseeing on the 26th (Thu): explore the fascinating underground world of Mammoth Cave Campground, look for gifts at Detweiler's Country Store, and then admire the majestic nature at Nolin Lake State Park.

For where to stay, ratings, photos, and more tourist information, refer to the Park City travel route planner.

Drive from Paducah to Park City in 3 hours. In December, daytime highs in Park City are 49°F, while nighttime lows are 32°F. Finish up your sightseeing early on the 26th (Thu) so you can travel to Louisville.

Things to do in Park City

Parks Nature Trails

Side Trips

Horse Cave, Glasgow, Nolin Lake State Park, Cedar Sink Trail, Detweiler's Country Store
Highlights from your plan
Cedar Sink Trail ©
Cedar Sink Trail
South Central Kentucky Cultural Center ©
Nolin Lake State Park ©
Nolin Lake State Park

4
nights
Louisville

Louisville ©
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. Let the collections at Conrad-Caldwell House Museum (Conrad's Castle) and 21c Museum Hotel capture your imagination. Monastery Immaculate conception and Lincoln Boyhood National Memorial are good opportunities to explore the local culture. When in Louisville, make a side trip to see Spring Mill State Park in Mitchell, approximately 1h 20 min away. And it doesn't end there: stroll around The Parklands of Floyds Fork, brush up on your knowledge of spirits at Kentucky Peerless Distilling Co, admire the masterpieces at The Speed Art Museum, and take a stroll through Old Louisville.

To see traveler tips, photos, other places to visit, and other tourist information, go to the Louisville trip builder site .

You can drive from Park City to Louisville in 1.5 hours. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In December, daily temperatures in Louisville can reach 48°F, while at night they dip to 33°F. Wrap up your sightseeing on the 30th (Mon) to allow time to travel to Middlesboro.

Things to do in Louisville

Historic Sites Museums Nature

Side Trips

Bartholomew County Veteran's Memorial, Lincoln Boyhood National Memorial, Historic District, Bear Wallow Distillery, Tibetan Mongolian Buddhist Cultural Center
Highlights from your plan
Frazier History Museum ©
Frazier History Museum
Lincoln Boyhood National Memorial ©
Lincoln Boyhood National Memorial

1
night
Middlesboro

Middlesboro ©
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. On the 31st (Tue), trek along Tri State Peak Trail, then get advice or help at Abraham Lincoln Library and Museum, and then examine the collection at Little Congress Bicycle Museum.

To see where to stay, reviews, photos, and more tourist information, refer to the Middlesboro itinerary builder .

You can drive from Louisville to Middlesboro in 3.5 hours. Traveling from Louisville to Middlesboro, you'll gain 1 hour due to the time zone difference. In December in Middlesboro, expect temperatures between 50°F during the day and 32°F at night. Wrap up your sightseeing on the 31st (Tue) early enough to travel to Lexington.

Things to do in Middlesboro

Parks Trails Outdoors

Side Trips

Cumberland Gap, Abraham Lincoln Library and Museum
Highlights from your plan
Tri State Peak Trail ©
Tri State Peak Trail
Abraham Lincoln Library and Museum ©
Little Congress Bicycle Museum ©
Little Congress Bicycle Museum

4
nights
Lexington

Lexington ©
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. John Rankin House and Lexington Cemetery will appeal to history buffs. Eschew the tourist crowds and head to Kentucky Gateway Museum Center and Raven Run Nature Sanctuary. Take a break from Lexington with a short trip to Carter Caves State Resort Park in Olive Hill, about 1h 45 min away. The adventure continues: indulge in some personalized pampering at some of the best spas, see the interesting displays at Headley-Whitney Museum, immerse yourself in nature at Kentucky Horse Park, and buy something for everyone on your list at Fayette Mall.

For where to stay, more things to do, traveler tips, and other tourist information, you can read our Lexington online visit planner .

Traveling by car from Middlesboro to Lexington takes 2.5 hours. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Expect a daytime high around 48°F in December, and nighttime lows around 32°F. Finish up your sightseeing early on the 4th (Sat) so you can travel to Frankfort.

Things to do in Lexington

Parks Museums Nature

Side Trips

John Rankin House, Kentucky Gateway Museum Center, Carter Caves State Resort Park
Highlights from your plan
Raven Run Nature Sanctuary ©
Raven Run Nature Sanctuary
Mary Todd Lincoln House ©
Mary Todd Lincoln House
Lexington Cemetery ©
Lexington Cemetery

3
nights
Frankfort

Frankfort ©
Frankfort is the capital city of the Commonwealth of Kentucky and the seat of Franklin County. Your list of things to see and do now includes Kentucky Military History Museum, Rebecca Ruth Candy Tours & Museum, Three Boys Farm Distillery, and other attractions. On the 5th (Sun), stroll the grounds of Kentucky Vietnam Veterans Memorial, brush up on your knowledge of spirits at Buffalo Trace Distillery, brush up on your knowledge of spirits at Glenns Creek Distillery, sample the fine beverages at Three Boys Farm Distillery, then see the interesting displays at Rebecca Ruth Candy Tours & Museum, and finally brush up on your military savvy at Kentucky Military History Museum. On the 6th (Mon), you'll have a packed day of sightseeing: see the interesting displays at Capital City Museum, then stroll the grounds of Frankfort Cemetery, then do a tasting at The Ridge Winery Tasting Room, and finally stop by The Outlet Shoppes of the Bluegrass.

To see reviews, other places to visit, more things to do, and other tourist information, use the Frankfort holiday site .

You can take a bus from Lexington to Frankfort in an hour. Another option is to drive. In January in Frankfort, expect temperatures between 41°F during the day and 23°F at night. Wrap up your sightseeing by early afternoon on the 7th (Tue) to allow enough time to travel back home.

Things to do in Frankfort

Museums Historic Sites Breweries & Distilleries

Side Trips

The Outlet Shoppes of the Bluegrass, Damselfly Gallery, Rising Sons Home Farm Winery, Basilica of St Joseph Proto-Cathedral, The Ridge Winery Tasting Room
Highlights from your plan
Castle & Key Distillery ©
Castle & Key Distillery
Rising Sons Home Farm Winery ©
Rising Sons Home Farm Winery

3
nights
Bowling Green

Bowling Green ©
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. You'll discover tucked-away gems like South Union Shaker Village and Historic Cragfont. Get a sense of the local culture at Bill Monroe's Home Place and Riverview at Hobson Grove. Explore Bowling Green's surroundings by going to Habbeger's Amish Market (in Scottsville), Sumner Crest WInery (in Portland) and Farmer Brown's Produce & General Store (in Gallatin). There's lots more to do: get engrossed in the history at The Kentucky Museum, Head underground at Lost River Cave, contemplate in the serene atmosphere at St. Joseph Catholic Church, and admire all the interesting features of NCM Motorsports Park.

For traveler tips, other places to visit, reviews, and other tourist information, you can read our Bowling Green trip tool .

Traveling by car from Frankfort to Bowling Green takes 3 hours. Alternatively, you can take a bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In January in Bowling Green, expect temperatures between 45°F during the day and 26°F at night. Finish your sightseeing early on the 10th (Fri) to allow enough time to travel to Danville.

Things to do in Bowling Green

Historic Sites Museums Shopping

Side Trips

Historic Cragfont, South Union Shaker Village, Farmer Brown's Produce & General Store, Bill Monroe's Home Place, Habbeger's Amish Market
Highlights from your plan
Bill Monroe's Home Place ©
Bill Monroe's Home Place
South Union Shaker Village ©
South Union Shaker Village
Sumner Crest WInery ©
Sumner Crest WInery

3
nights
Danville

Danville ©
Danville is a home rule-class city in Boyle County, Kentucky, in the United States. Start off your visit on the 11th (Sat): take in the history at Millsprings Battlefield Museum, then learn about winemaking at Cave Hill Vineyard & Winery, then examine the collection at The Great American Dollhouse Museum, and finally stop by Kentucky Soaps and Such. Get ready for a full day of sightseeing on the 12th (Sun): immerse yourself in nature at Lake Cumberland State Resort Park and then look for all kinds of wild species at Cumberland Point Recreational Area.

To find maps, photos, and other tourist information, you can read our Danville trip planner .

Getting from Bowling Green to Danville by car takes about 2.5 hours. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In January, plan for daily highs up to 41°F, and evening lows 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

Side Trips

Nancy, Cave Hill Vineyard & Winery, Kentucky Soaps and Such, Lake Cumberland State Resort Park
Highlights from your plan
The Great American Dollhouse Museum ©
Lake Cumberland State Resort Park
Lake Cumberland State Resort Park
Cave Hill Vineyard & Winery ©
Cave Hill Vineyard & Winery

3
nights
Elizabethtown

Elizabethtown ©
Elizabethtown is a home rule-class city and the county seat of Hardin County, Kentucky, in the United States. Discover out-of-the-way places like Swope's Cars of Yesteryear Museum and Blue Heron Vineyard & Winery. 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) and Otter Creek Outdoor Recreation Area (in Brandenburg). There's much more to do: see the interesting displays at Brown-Pusey House, sample the fine beverages at Boundary Oak Distillery, browse the different shops at The Glendale Antique Mall, and make a trip to Kentucky September 11th Memorial.

For reviews, photos, maps, and more tourist information, you can read our Elizabethtown attractions planning tool .

Drive from Danville to Elizabethtown in 1.5 hours. Expect a daytime high around 41°F in January, and nighttime lows around 23°F. Finish your sightseeing early on the 16th (Thu) to allow enough time to travel to Berea.

Things to do in Elizabethtown

Museums Wineries Parks

Side Trips

Rockport, Radcliff, The Glendale Antique Mall, Blue Heron Vineyard & Winery, Otter Creek Outdoor Recreation Area
Highlights from your plan

3
nights
Berea

Berea ©
Berea is a home rule-class city in Madison County, Kentucky, in the United States. You've added Berea Cemetery, Old Town Fudge Factory, Todd's Antique Mall, and other attractions to your itinerary. Kick off your visit on the 17th (Fri): stroll the grounds of Berea Cemetery, look for gifts at Log House Craft Gallery, stop by Old Town Fudge Factory, then wander the streets of Artisan Village District, then browse the different shops at Todd's Antique Mall, and finally appreciate the history behind Fitchburg Furnace. On the 18th (Sat), you'll have a packed day of sightseeing: shop like a local with Berea Arts Council, see the interesting displays at Kentucky Music Hall of Fame, then contemplate the long history of William Whitley House, and finally learn about winemaking at Cedar Creek Vineyards.

For traveler tips, more things to do, photos, and tourist information, go to the Berea trip itinerary maker website .

Getting from Elizabethtown to Berea by car takes about 2.5 hours. In January, daily temperatures in Berea can reach 40°F, while at night they dip to 23°F. Wrap up your sightseeing by early afternoon on the 19th (Sun) to allow time for travel back home.

Things to do in Berea

Museums Shopping Historic Sites

Side Trips

Fitchburg Furnace, Cedar Creek Vineyards, Kentucky Music Hall of Fame, William Whitley House, Three Forks Historical Center
Highlights from your plan
Three Forks Historical Center ©
Three Forks Historical Center
Log House Craft Gallery ©
Log House Craft Gallery
William Whitley House ©
William Whitley House

3
nights
Versailles

Versailles ©
Versailles is a home rule-class city in Woodford County, Kentucky, United States and is located near Lexington. Get in touch with nature at Coolmore America - Ashford Stud and Old Frankfort Pike. Give yourself a bit of retail therapy at Irish Acres Gallery of Antiques and Downtown Midway Kentucky. Next up on the itinerary: learn about winemaking at Wildside Winery, admire all the interesting features of Old Friends at Dream Chase Farm, sample the tasty concoctions at Woodford Reserve Distillery, and admire the landmark architecture of Jack Jouett House Historic Site.

To see photos, maps, ratings, and more tourist information, go to the Versailles day trip planning site .

Traveling by car from Berea to Versailles takes an hour. In January, daytime highs in Versailles are 41°F, while nighttime lows are 24°F. Finish your sightseeing early on the 22nd (Wed) to allow enough time to drive to Lawrenceburg.

Things to do in Versailles

Shopping Scenic Drive Outdoors

Side Trips

Midway, Old Friends at Dream Chase Farm, Old Frankfort Pike
Highlights from your plan
Irish Acres Gallery of Antiques ©
Irish Acres Gallery of Antiques
The Castle ©
The Castle
Equus Run Vineyard & Winery ©
Equus Run Vineyard & Winery

3
nights
Lawrenceburg

Lawrenceburg ©
Lawrenceburg is a home rule-class city in Anderson County, Kentucky, United States. On the 23rd (Thu), sample the fine beverages at Wild Turkey Distillery, then view the masterpieces at Elements Clay Studio and Stuff, then brush up on your knowledge of spirits at Four Roses Bourbon - Warehouse and Bottling Facility, and finally brush up on your knowledge of spirits at Four Roses. Keep things going the next day: learn about winemaking at Lovers Leap Vineyards and Winery.

For photos, ratings, and more tourist information, use the Lawrenceburg online tour planner .

Lawrenceburg is just a stone's throw from Versailles. In January, daily temperatures in Lawrenceburg can reach 41°F, while at night they dip to 23°F. On the 25th (Sat), you're off toBardstown.

Things to do in Lawrenceburg

Breweries & Distilleries Museums Shopping

Side Trip

Four Roses Bourbon - Warehouse and Bottling Facility
Highlights from your plan
Lovers Leap Vineyards and Winery ©
Lovers Leap Vineyards and Winery
Wild Turkey Distillery ©
Wild Turkey Distillery

3
nights
Bardstown

Bardstown ©
Bardstown is a home rule-class city in Nelson County, Kentucky, in the United States. The Abbey of Gethsemani and My Old Kentucky Home will appeal to history buffs. Eschew the tourist crowds and head to McIntyre's Winery & Berries and Bardstown Art Gallery. Explore the numerous day-trip ideas around Bardstown: Campbellsville (Atkinson-Griffin Log House-Confederate Hospital & Green River Lake State Park) and Limestone Branch Distillery (in Lebanon). There's lots more to do: look for gifts at Kentucky Bourbon Marketplace Bar & Tasting Room, see the interesting displays at Oscar Getz Museum of Whiskey History, learn about winemaking at Wight - Meyer Vineyard & Winery, and brush up on your knowledge of spirits at Preservation Distillery.

To see traveler tips, maps, reviews, and tourist information, you can read our Bardstown trip builder website .

Getting from Lawrenceburg to Bardstown by car takes about an hour. Expect a daytime high around 41°F in January, and nighttime lows around 23°F. Finish your sightseeing early on the 28th (Tue) so you can drive to Harrodsburg.

Things to do in Bardstown

Wineries Museums Parks

Side Trips

Campbellsville, Lebanon, Shepherdsville, The Abbey of Gethsemani, Springhill Winery
Highlights from your plan
McIntyre's Winery & Berries ©
McIntyre's Winery & Berries
The Abbey of Gethsemani ©
The Abbey of Gethsemani
Limestone Branch Distillery ©
Limestone Branch Distillery

3
nights
Harrodsburg

Harrodsburg ©
Harrodsburg is a home rule-class city in Mercer County, Kentucky, in the United States. 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 do a tasting at Horseshoe Bend Vineyards and WineryHorseshoe Bend Vineyards and Winery, and finally take in the history at Perryville Battlefield State Historic Site.

For more things to do, photos, where to stay, and other tourist information, go to the Harrodsburg visit planner .

Traveling by car from Bardstown to Harrodsburg takes an hour. In January, plan for daily highs up to 41°F, and evening lows to 23°F. On the 31st (Fri), you'll travel to Hopkinsville.

Things to do in Harrodsburg

Historic Sites Wineries

Side Trips

Perryville Battlefield State Historic Site, Horseshoe Bend Vineyards and WineryHorseshoe Bend Vineyards and Winery
Highlights from your plan
Shaker Village of Pleasant Hill ©
Shaker Village of Pleasant Hill
Old Fort Harrod State Park ©
Old Fort Harrod State Park

2
nights
Hopkinsville

Hopkinsville ©
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Start off your visit on the 31st (Fri): sample the fine beverages at Casey Jones Distillery. On the next day, stop by Griffin's Studio, see the interesting displays at Robert Penn Warren Birthplace Museum, and then witness the site of a historic battle at Fort Donelson National Battlefield.

To find traveler tips, reviews, ratings, and other tourist information, use the Hopkinsville trip itinerary planner .

Traveling by car from Harrodsburg to Hopkinsville takes 3 hours. The time zone difference when traveling from Harrodsburg to Hopkinsville is minus 1 hour. In January, plan for daily highs up to 44°F, and evening lows to 27°F. You'll have a few hours on the 2nd (Sun) to wrap things up before traveling home.

Things to do in Hopkinsville

Historic Sites Parks Nature

Side Trips

Jefferson Davis State Historic Site, Fort Donelson National Battlefield, Robert Penn Warren Birthplace Museum
Highlights from your plan
Fort Donelson National Battlefield ©
Casey Jones Distillery ©
Casey Jones Distillery
Robert Penn Warren Birthplace Museum ©

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