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  • Family touring Mammoth Cave National Park in Kentucky
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    Mammoth Cave, Art and Kentucky’s Fabled Spirits History

  • A horse race at Keeneland in Lexington, Kentucky
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    Lexington’s Equestrian Culture, Presidential History and Cuisine

  • Posing for a photo at Libby Hill Park in Richmond, Virginia
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    Richmond’s Neighborhoods, Street Art and Dining Scene

  • Hiking to incredible views in Shenandoah National Park, Virginia
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    Scenic Overlooks and Cascading Waterfalls in Shenandoah National Park

  • View of the Washington Monument from the Lincoln Memorial in Washington, D.C.
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    Gorgeous Gardens and Picturesque Estates in Virginia and Beyond

Pausing to watch the sunrise while driving along Skyline Drive in Shenandoah National Park, Virginia
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Kentucky and Virginia Road Trip: Cultural Gems, Natural Wonders and Local Hot Spots

By Kelly Larson

  • Route distance:
    1,526 km
  • Suggested Time:
    5 days

This five-day road trip through the southeastern USA features a little bit of everything: unique museums, horse country, craft beverages, natural wonders and iconic historic sites.

Toss your bags in the trunk of your rental car, stock up on your favorite snacks and get ready for a road trip through some of the most enticing places in Kentucky and Virginia. You’ll tour the world’s longest cave system and sample craft spirits straight from the source in Kentucky, then savor delicious cuisine and see an unforgettable mountain sunrise in Virginia. Fly into Louisville Muhammad Ali International Airport (SDF) in Kentucky to begin your journey through stunning natural landscapes and vibrant cities.

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Family touring Mammoth Cave National Park in Kentucky
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Mammoth Cave, Art and Kentucky’s Fabled Spirits History

Your first stop, Louisville, is known as the home of the Kentucky Derby and for its bourbon distilleries. After a great night’s rest at the Louisville Marriott Downtown, grab some brunch and walk or drive through the lively streets of the East Market District to Copper and Kings American Brandy Company. There, you’ll learn all about the barrel-aging process, sample limited-release spirits and even fill your own signed and dated bottle as part of the distillery’s Barrel-to-Bottle Experience. Next, adventure awaits an hour-and-a-half drive south of the city at the world’s longest cave system, Mammoth Cave National Park. Take the two-hour Historic Tour to meander through ancient tunnels, descend to exhilarating depths and marvel at massive chambers while learning about the cave from an experienced guide. Follow the Kentucky sunshine back to the surface and hop back in the car for two hours until you reach your next destination: the flirty and sophisticated 21c Museum Hotel Lexington. Each room is unique in this boutique hotel, which also houses a contemporary art museum. From the hotel, it’s a short, five-minute walk up West Main Street to Tony’s of Lexington for a juicy steak and a nightcap as you reflect upon the day’s adventures. But rest up – your epic Southeastern road trip is just beginning.

354 km
3.5 hours by car
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A horse race at Keeneland in Lexington, Kentucky
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Lexington’s Equestrian Culture, Presidential History and Cuisine

Today is all about the historic but hip college town of Lexington in Kentucky’s horse country. Kick it off with a quick elevator ride downstairs to 21c Museum Hotel Lexington’s restaurant, Lockbox, where chef-driven frittatas and breakfast sandwiches await. You’ll need that energy, because no visit to the Horse Capital of the World is complete without a trip to the fabled Keeneland horse track and auction house. From the hotel, drive 15 minutes west on Versailles Road and grab tickets for the Morning Works Tour for an overview of the historic grounds, including a stroll through the Paddock and Grandstand. After grabbing a bite at local staple Third Street Stuff & Coffee, explore the shops and galleries of The Square, see downtown’s giant Abraham Lincoln mural and visit the Mary Todd Lincoln House. Now a museum, this was the childhood home of Abraham Lincoln’s wife, where you can learn about her family and see artifacts from the Lincolns’ life (closed in winter; online booking is recommended). Of the many ways you could spend your last hours in this colorful city, consider a trip to one of more than 20 breweries like Ethereal Brewing or West Sixth Brewing. Adjacent to West Sixth is Smithtown Seafood, a great casual spot to load up on shrimp and grits or the local-favorite fried catfish as you look forward to the next leg of your road trip. Tomorrow, it’s time to cross state lines and head toward Virginia.

790 km
7.5 hours by car
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Posing for a photo at Libby Hill Park in Richmond, Virginia
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Richmond’s Neighborhoods, Street Art and Dining Scene

Richmond, Virginia is a charming and edgy river town that’s making quite a name for itself in the culinary, nightlife and brewing scenes. To get there from your hotel in Lexington, it’ll take just over seven hours heading east on Interstate 64. Stop along the way, stretch your legs and grab brunch at the Capitol Market in scenic Charleston, West Virginia. After your scenic drive through the Mountain State, you’ll be checking into the Omni Richmond Hotel next to the James River in the heart of downtown. Take in the city’s colorful murals and Victorian architecture on your way to Stella’s Grocery, a gourmet market where you’ll stock up on breakfast, lunch and snack staples. You’ll need them for the outdoor adventures on the next leg of the journey. Before settling in for the night, take a stroll along the Canal Walk and pick out a dinner restaurant from one of the many options, whether you’re craving tacos and margaritas at Casa Del Barco or an elegant experience at Bateau. Make sure to get some rest: tomorrow will come early and, if you’re up for it, might even involve a waterfall or two.

187 km
2.25 hours by car
04
Hiking to incredible views in Shenandoah National Park, Virginia
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Scenic Overlooks and Cascading Waterfalls in Shenandoah National Park

Just over two hours northwest of Richmond lies the Thornton Gap Entrance Station of Virginia’s stunning Shenandoah National Park. It’s the opening scene of your adventurous day trip filled with hiking and exploring the beautiful Blue Ridge Mountains. With a good cup of coffee in the cupholder, take a morning ride along Skyline Drive. As sunrise approaches, make sure to pull over at one of the stunning overlooks to fully appreciate the moment. Tunnel Parking, Buck Hollow, Hazel Mountain and Thorofare Mountain are all great options. After filling your camera roll with some of Virginia’s most stunning peaks and valleys, find your way to the Fishers Gap parking area, gateway to the majestic Rose River Falls. The falls cascade over 20 meters and can be reached after a short hike over fire roads, rocky inclines and scenic bridges. Enjoy your picnic lunch from the Rose River Loop Trail high above the falls. Once you’ve had your fill of adventure, head back to the hotel to freshen up before exploring the bohemian streets of Richmond’s Carytown district and its murals, record stores and vintage boutiques. The eclectic Can Can Brasserie will welcome you for steak frites and oysters as you recount the day’s adventures over a glass of wine.

195 km
2.25 hours by car
05
View of the Washington Monument from the Lincoln Memorial in Washington, D.C.
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Gorgeous Gardens and Picturesque Estates in Virginia and Beyond

After a latte and breakfast sandwich from Richmond’s Urban Farmhouse Market & Café, it’s time to check out and head toward your last stops in Virginia. Hop on Interstate 95 north to Lakeside’s Lewis Ginter Botanical Garden. Stroll more than a dozen themed gardens and the glass-domed conservatory, then head north two hours to George Washington’s Mount Vernon. The historic, riverfront estate, where the nation’s first president and his wife Martha lived, is one the USA’s most visited historic homes. An added bonus on your southeastern road trip is a short stay in the nation’s capital city, Washington, D.C. Drive just 30 more minutes to the JW Marriott Washington, D.C., check in and head less than a block away to Hotel Washington’s VUE rooftop bar for a craft cocktail and outstanding views of The White House and the Washington Monument. In the morning, set aside some time to tour the National Mall and nearby outdoor monuments before returning your car and catching a flight home from Washington Dulles International Airport (IAD) or Baltimore/Washington International Thurgood Marshall Airport (BWI).