14 days in Kentucky & North Carolina Itinerary

14 days in Kentucky & North Carolina Itinerary

Created using Inspirock United States tour itinerary maker

Make it your trip
Fly
1
Lexington
— 2 nights
Drive
2
Mammoth Cave National Park
— 2 nights
Drive
3
Middlesboro
— 1 night
Drive
4
Highlands
— 2 nights
Drive
5
Asheville
— 4 nights
Drive
6
Raleigh
— 2 nights
Fly

S M T W T F S
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Lexington

— 2 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.
Eschew the tourist crowds and head to Unique Horse Farm Tours and Mary Todd Lincoln House. Get in touch with nature at Natural Bridge State Resort Park and Louisville Mega Cavern. Get out of town with these interesting Lexington side-trips: Kentucky Artisan Distillery (in Crestwood) and Red River Gorge Geological Area (in Winchester). There's still lots to do: sample the tasty concoctions at Lexington Brewing & Distilling Co. and brush up on your knowledge of spirits at Bluegrass Distillers.

To plan Lexington vacation without wasting time, ask Inspirock to design an itinerary.

New York City to Lexington is an approximately 4-hour flight. You can also drive; or take a bus. Traveling from New York City in November, expect little chillier with lows of 36°F in Lexington. Wrap up your sightseeing on the 17th (Tue) early enough to drive to Mammoth Cave National Park.

Things to do in Lexington

Parks · Nature · Wildlife · Outdoors

Side Trips

Mammoth Cave National Park

— 2 nights
Mammoth Caves National Park is the longest cave system in the world so far discovered.
Start off your visit on the 18th (Wed): hike along Tall Man's Misery, stroll through Fat Man's Misery, and then explore the fascinating underground world of Mammoth Cave. Here are some ideas for day two: explore the fascinating underground world of Diamond Caverns, get interesting insight from Tours, and then trek along Cedar Sink Trail.

To see where to stay, other places to visit, maps, and more tourist information, read Mammoth Cave National Park trip maker site.

Traveling by car from Lexington to Mammoth Cave National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. Due to the time zone difference, you'll gain 1 hour traveling from Lexington to Mammoth Cave National Park. Expect a daytime high around 57°F in November, and nighttime lows around 36°F. Wrap up your sightseeing on the 19th (Thu) early enough to travel to Middlesboro.

Things to do in Mammoth Cave National Park

Parks · Outdoors · Trails · Nature

Side Trip

Middlesboro

— 1 night
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Kick off your visit on the 20th (Fri): explore the striking landscape of Cumberland Gap National Historical Park.

To find where to stay, reviews, ratings, and more tourist information, use the Middlesboro trip planner.

Traveling by car from Mammoth Cave National Park to Middlesboro takes 3.5 hours. November in Middlesboro sees daily highs of 58°F and lows of 34°F at night. Wrap up your sightseeing on the 20th (Fri) early enough to travel to Highlands.

Things to do in Middlesboro

Nature · Parks
Highlights from your trip

Highlands

— 2 nights
Highlands is an incorporated town in Macon County in the U.S. state of North Carolina. Start off your visit on the 21st (Sat): take in the dramatic scenery at Glen Falls and then fly down the slopes at Scaly Mountain Outdoor Center. Here are some ideas for day two: admire the sheer force of Whitewater Falls, take your sightseeing to a higher altitude at Sunset Rock and Ravenel Park, and then take in the awesome beauty at Whiteside Mountain.

For maps, more things to do, traveler tips, and other tourist information, read Highlands travel itinerary planner.

Traveling by car from Middlesboro to Highlands takes 3.5 hours. You'll lose 1 hour traveling from Middlesboro to Highlands due to the time zone difference. In November, daily temperatures in Highlands can reach 60°F, while at night they dip to 32°F. Finish your sightseeing early on the 22nd (Sun) to allow enough time to drive to Asheville.

Things to do in Highlands

Parks · Nature · Winter Sports · Outdoors

Side Trips

Asheville

— 4 nights

Land of the Sky

Asheville nestles between two major mountain ranges in the scenic western section of North Carolina.
You'll explore the less-touristy side of things at The North Carolina Arboretum and Tumblestone Tours and Transportation. Escape the urban bustle at Pisgah National Forest and Cataloochee Valley. You'll find plenty of places to visit near Asheville: DuPont State Recreational Forest (in Cedar Mountain), Pearson's Falls and Glen (in Saluda) and Max Patch (in Hot Springs). There's much more to do: get a taste of the local shopping with Lexington Glassworks, sample the tasty concoctions at Sierra Nevada Brewing Co. Tours & Tastings, and view the masterpieces at Colin's Creatures.

Discover how to plan a Asheville trip in just a few steps with Inspirock's itinerary builder.

Getting from Highlands to Asheville by car takes about 2 hours. November in Asheville sees daily highs of 59°F and lows of 36°F at night. Wrap up your sightseeing on the 26th (Thu) early enough to drive to Raleigh.

Things to do in Asheville

Parks · Nature · Wildlife · Outdoors

Side Trips

Raleigh

— 2 nights

City of Oaks

For those not from the South, Raleigh might be one of the region's better-kept travel secrets.
On the 27th (Fri), tour the pleasant surroundings at Neuse River Trail, then immerse yourself in nature at Umstead State Park, and then stroll around Pullen Park. Get ready for a full day of sightseeing on the 28th (Sat): hike along American Tobacco Trail, look for all kinds of wild species at Carolina Tiger Rescue, and then view the masterpieces at Liquidambar Gallery and Gifts.

To find where to stay, photos, other places to visit, and more tourist information, use the Raleigh trip planner.

Traveling by car from Asheville to Raleigh takes 4 hours. Alternatively, you can fly; or take a bus. In November, daytime highs in Raleigh are 62°F, while nighttime lows are 39°F. Wrap up your sightseeing on the 28th (Sat) early enough to fly back home.

Things to do in Raleigh

Parks · Wildlife · Outdoors · Trails

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.

North Carolina travel guide

4.4
Historic Sites · Specialty Museums · Zipline
The Tar Heel State
A top destination for a holiday in nature, North Carolina provides a seemingly endless variety of outdoor activities, including hiking, mountain climbing, and skiing. While the state's rural regions offer a taste of traditional Appalachian music and culture, its increasingly diverse big cities feature modern skyscrapers, renowned museums, and historical neighborhoods perfect for sightseeing tours. The coastal region, famous for its year-round temperate climate, attracts millions of annual visitors, making North Carolina the sixth most-visited state in the country. Though it's hard to find a quiet time of year in coastal North Carolina, the state's inland areas retain many secluded corners where you can experience the laid-back Old South atmosphere.