Road trip from Madison to Lexington
All Category
Sights & Landmarks
Shopping
Nightlife
Food & Drink
Spas & Wellness
Outdoor Activities
All Category
Sights & Landmarks
Shopping
Nightlife
Food & Drink
Spas & Wellness
Outdoor Activities
Reset
Show less
ITINERARY
9h 54m518 miles12 stops
1
First Unitarian Meeting House of Madison
2
Alliant Energy Center
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
3
Arista Spa & Salon
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
4
Wrigley Field
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
5
Boystown
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
6
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
7
Barrels & Billets
An exciting bourbon experience where guests can blend, create and bottle their very own bourbon. Guests will blend with six award-winning WoodCraft bourbons which includes a 200 Year Oak, European Oak, American Oak, Cherry Wood, Maple Wood, and Smoked Oak. During the experience, guests will learn the art of bourbon blending before the blending process begins. Once the blending experience is complete, guests can have their recipe bottled onsite.
8
Angel's Envy Distillery
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
9
Lexington Brewing & Distilling Co.
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
10
Trust Lounge
11
Fayette Mall
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
12
Waveland State Historic Site
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
Customize this Trip
OVERVIEW
1
Start:First Unitarian Meeting House of Madison
Madison, Wisconsin·
4.5
(96) review
900 University Bay Dr, Madison, WI 53705-2298
2
Start:Alliant Energy Center
Madison, Wisconsin·
4.0
(99) review
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
3
Start:Arista Spa & Salon
Naperville, DuPage County, Illinois·
4.0
(9) review
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
4
Start:Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
5
Start:Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
6
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
7
Start:Barrels & Billets
Louisville, Kentucky·
4.0
(9) review
An exciting bourbon experience where guests can blend, create and bottle their very own bourbon. Guests will blend with six award-winning WoodCraft bourbons which includes a 200 Year Oak, European Oak, American Oak, Cherry Wood, Maple Wood, and Smoked Oak. During the experience, guests will learn the art of bourbon blending before the blending process begins. Once the blending experience is complete, guests can have their recipe bottled onsite.
8
Start:Angel's Envy Distillery
Louisville, Kentucky·
4.5
(967) review
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
9
Start:Lexington Brewing & Distilling Co.
Lexington, Kentucky·
4.5
(984) review
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
10
Start:Trust Lounge
Lexington, Kentucky·
3.0
(9) review
123 W Main St, Lexington, KY 40507-1320
11
Start:Fayette Mall
Lexington, Kentucky·
4.5
(91) review
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
12
Start:Waveland State Historic Site
Lexington, Kentucky·
4.5
(97) review
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Madison to Little Rock
711 miles
13h 13m
17 stops
Fun & GamesTraveler ResourcesSights & LandmarksNature & ParksTours
Madison to Spokane
1,629 miles
28h 11m
10 stops
Sights & LandmarksFood & DrinkShoppingNightlifeMuseums
Madison to Greenville
833 miles
16h 19m
24 stops
Outdoor ActivitiesShoppingSights & LandmarksNightlifeNature & Parks
Madison to Denton
999 miles
18h 3m
22 stops
ShoppingNature & ParksFun & GamesNightlifeTraveler Resources
Madison to Lancaster
839 miles
15h 38m
27 stops
Nature & ParksMuseumsNightlifeSights & LandmarksOutdoor Activities
Madison to Oakland
2,090 miles
36h 13m
24 stops
Sights & LandmarksNature & ParksWater & Amusement ParksMuseumsFun & Games
EXPLORE OTHER
Check Out Different Road Trip Options
Phoenix to New Haven
2,543 miles
45h 45m
32 stops
MuseumsOutdoor ActivitiesToursFun & GamesFood & Drink
Richmond to Norfolk
92 miles
1h 58m
26 stops
Nature & ParksTraveler ResourcesToursSights & LandmarksFun & Games
San Francisco to Gastonia
2,697 miles
47h 59m
40 stops
MuseumsSights & LandmarksNature & ParksShoppingNightlife
Anchorage to Roanoke
4,231 miles
84h 25m
35 stops
Food & DrinkConcerts & ShowsShoppingMuseumsSights & Landmarks
Lakewood to Chicago
1,012 miles
17h 55m
26 stops
MuseumsNightlifeSpas & WellnessFood & DrinkShopping
Memphis to Merced
1,981 miles
34h 36m
22 stops
ToursFun & GamesOutdoor ActivitiesNature & ParksConcerts & Shows
FAQ
Frequently Asked Questions
What's the driving distance between Madison and Lexington?
The distance is 518 miles
What's the travel time between Madison and Lexington?
The driving time can vary depending on traffic conditions, but it is typically 9h 54m mins in normal traffic
What are some of the best cities to visit between Madison and Lexington?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Lexington?
There are plenty! Here are some stops you shouldn’t miss on your way to Lexington
What’s the weather like in Lexington?
The weather in Lexington is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Lexington in January
Weather in Lexington in February
Weather in Lexington in March
Weather in Lexington in April
Weather in Lexington in May
Weather in Lexington in June
Weather in Lexington in July
Weather in Lexington in August
Weather in Lexington in September
Weather in Lexington in October
Weather in Lexington in November
Weather in Lexington in December
Interested in a detailed plan for your time in Lexington?
Plan your dream Lexington trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Lexington
A 2-day itinerary in Lexington
A 3-day itinerary in Lexington
A 4-day itinerary in Lexington
A 5-day itinerary in Lexington
A 6-day itinerary in Lexington
Where else can I travel to if I'm starting my trip in Madison?
We have a lot of great trip options for Madison! See the links below for all the itineraries we created for you