A stone bridge spanning a river with fall foliage on the banks.

Cumberland Falls Bridge. Photo courtesy of Kentucky Tourism.

Let’s be honest: The trip outlined here is a bit crazy. It’s an ambitious attempt to get you to see the best of Kentucky in just two weeks. What you really need is a month, or better yet, a lifetime, but most people just don’t have that amount of time. So consider this your sampler platter, your chance to savor the best of the best. You’re not going to see everything—not in the state, and not even in each destination—but you’ll get a taste of what Kentucky has to offer, so next time you can dive in deeper.

Day 1

Start in Louisville with a day of museum-hopping. Begin downtown with a visit to the Louisville Slugger Museum & Factory to immerse yourself in all things baseball, then head to the Muhammad Ali Center to air box with The Greatest. If history is more your thing, swap the Ali Center for the Frazier International History Museum to see their remarkable collection of artifacts. In the afternoon, head south to the Kentucky Derby Museum, where you’ll get to pop in at historic Churchill Downs. Grab dinner in NuLu—maybe at Decca or Rye—and then splurge for a room at 21C Museum Hotel or enjoy the atmosphere at one of Old Louisville’s B&Bs.

Day 2

A lot of driving awaits, so wake up early and travel to Paducah in far western Kentucky. Art is at the heart of Paducah, so make sure the National Quilt Museum and the Lower Town Arts District both make it onto your itinerary. Enjoy dinner at Cynthia’s and then have sweet dreams in one of the enormous suites at Fox Briar Inn.

Day 3

Start your journey back east with a short drive to Land Between the Lakes. Stop at Kentucky Dam Village State Resort Park and rent a boat, and go for a morning cruise on beautiful Kentucky Lake, the largest man-made lake east of the Mississippi. Dedicate your afternoon to exploring Land Between the Lakes National Recreation Area. You can go for a hike or a horseback ride, or visit the Nature Station or The Homeplace. Sit down to a plate of fried fish at Catfish Kitchen, then pitch a tent and sleep under the stars at one of the many campgrounds.

Day 4

Continue east to Bowling Green to admire the hot rods at the National Corvette Museum. In the afternoon, hop on I-65 and drive north to Cave Country to explore Mammoth Cave or the cave of your choice. The national park is a good place to have a picnic dinner before making your way north past Munfordville to Country Girl at Heart Farm Bed and Breakfast, where you can get a peaceful night’s sleep.

Day 5

After breakfast, make your way to Bardstown to say hello to My Old Kentucky Home and then get started on the Bourbon Trail. You have your choice of distilleries, but stop at Maker’s Mark in Loretto if you have time for only one. After your tour, continue on to Harrodsburg, where the Beaumont Inn is the place to go for both dinner and a room.

Day 6

Try to be at Shaker Village when it opens so that you have time to peek into the many buildings and watch the demonstrations. If you wish, have lunch there before continuing north to Frankfort, Kentucky’s capital city. With little time in Frankfort, make the Center for Kentucky History your destination. Plan for dinner at Rick’s White Light Diner and then see if a room is available at The Meeting House Bed and Breakfast.

Day 7

From Frankfort, it’s on to Northern Kentucky, where the Newport Aquarium is a must. Between Newport and Covington, you have a slew of dining and hotel options, so let your mood guide you. In the evening, enjoy a view of both the Northern Kentucky and Cincinnati skylines while on a cruise with BB Riverboats. End the night with a stein of beer at the Hofbräuhaus Newport.

Day 8

Put on your hiking boots this morning, as today is going to be an outdoor adventure. Travel south to Red River Gorge, a nature lover’s paradise in the Daniel Boone National Forest. You can hike to sandstone arches and waterfalls, paddle down the Red River, or try your hand at rock climbing on some of the east’s best routes. Rent a cabin in the gorge or book a room at Natural Bridge State Resort Park.

Day 9

Drive an hour east from Red River Gorge to Paintsville, located on the Country Music Highway in Kentucky’s Appalachians. See if Herman is available to give you a tour of Butcher Hollow, the birthplace of Loretta Lynn, then explore Mountain HomePlace. In the evening, head south to Jenny Wiley State Resort Park in Prestonsburg, where you’ll spend the night. Try to catch a show at either the Mountain Arts Center or the Jenny Wiley Theatre.

Day 10

Put on some country music as you continue down the highway to Pikeville, where you can spend your morning on the Hatfield-McCoy Feud Driving Tour or getting back to nature at Breaks Interstate Park. In the afternoon, head west to the coal company towns of Benham and Lynch, where you’ll want to make time for a tour of Portal 31 and a visit to the Kentucky Coal Mining Museum. The Benham School House Inn welcomes you to overnight in a former school.

Day 11

Rise and shine early to see if you can spot any black bears at Kingdom Come State Park before continuing west to Middlesboro and Cumberland Gap National Historical Park. Sign up for the trip to the Hensley Settlement, where you’ll get a taste of Appalachian homestead life. In the evening, watch the sunset from the Pinnacle Overlook. You’ll sleep well at Cumberland Manor Bed and Breakfast.

Day 12

Make it to Stearns in time for the morning departure of the Big South Fork Scenic Railway, which chugs its way through scenic forest to the Blue Heron Coal Mining Camp, which is interpreted by the National Park Service. Really immerse yourself in the region’s coal mining history with an afternoon visit to Barthell Coal Mining Camp, a perfect reconstruction of the former camp. For a unique experience, overnight in one of the miner’s cabins.

Day 13

Cruise north to the town of Berea, Kentucky’s folk arts and crafts capital, passing Cumberland Falls State Resort Park on your way. Spend your day in Berea hopping between the galleries and workshops of the town’s studio artists, where you can watch them at work and do a bit of shopping. Try for an early dinner reservation at Boone Tavern, where you’ll also spend the night. For evening entertainment, backtrack to Renfro Valley to catch one of their jamborees.

Day 14

Your tour of Kentucky ends in Lexington, where horses will be the theme. Sign up for a tour of a horse farm and then spend a few hours at the Kentucky Horse Park. If the Keeneland meets are going on, abandon all plans and go to the races. You’ll have a hard time choosing among the many fine restaurants in the region, but if you can get a reservation at Holly Hill Inn in nearby Midway, take it. With wonderful B&B options, Midway or Versailles is a good place to spend the night.

Color travel map of Kentucky


Excerpted from the Second Edition of Moon Kentucky.