Backroads & Bluegrass: Completely Kentucky

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Kentucky is mountain landscapes and rolling rural pasturelands where horses run on acres of bluegrass. It is one of the most picturesque states in the country. Today known for its horses, with many thoroughbred stud farms centered around Lexington. The Kentucky Derby, one of the most prestigious horse races takes place in Louisville. This state is also famous for its downhome style of country music and Highway 23 along the eastern border has been designated the Country Music Highway. With miles of sandy beaches, historic picturesque cities, stunning rugged wilderness of the Blue Ridge and Appalachian Mountains, and rolling hills and valleys of the foothills, Kentucky has it all. The state combines the friendliness of the south, the rural frontier and history of the west, the industry of the north, and the aristocratic charm of the east. 

Kentucky offers travelers sheer delight. This 40,000 square mile stretch of land is home to a greater variety of distant cultures than any other rural state within the United States. Where the edges of the state of Kentucky overlap, delightful contrasts abound. Contradictions started with Daniel Boone. He was torn between wanting his fellow pioneers to settle the land he loved passionately and yet not trusting that the pioneers would merge with the native people who loved and adopted him. Kentucky has an unequalled tradition of music, dance, and fine arts. Its geography is both fauna and flora. Vast big sky dominates the western regions. Acre after acre of flat country, also swampland, high fertile, and livestock continue to make the region wealthy and world famous. The east Kentucky mountains are well supplied with coal and iron ore, beautiful streams, and the world’s most spectacular caverns! All this makes Kentucky a place we must visit together! 

Day 1 – Home to Bloomington, IL 

Travel day today through Wisconsin and into central Illinois. Be alert to emerging signs of spring as we motor south. 

Included Meals: Welcome Dinner 

Hotel: Holiday Inn 

Day 2 – Bloomington to Paducah, KY 

A hot breakfast at our hotel is ready as we arise. We continue through Illinois, and shortly after lunch we cross the Interstate 24 Bridge over the scenic Ohio River, entering Kentucky where our adventure begins. (A little-known fact: The Ohio River is considerably bigger than the Mississippi at this point just upstream from where they join.) We immediately find ourselves in Paducah at the Whitehaven Welcome Center, a majestic landmark built in the 1860’s, cherished by the citizens of Paducah and listed on the National Register of Historic Places. We are met there by Kentucky representatives and hosted to an official “Welcome to Kentucky” reception. We are treated to a guided tour of Paducah, highlighted by an interpretive tour of the National Quilt Museum. This amazing place features artwork created with fabric and thread. A world famous, global destination featuring the best in quilt & fiber art. One does not have to be a quilter to appreciate this exhibit! Other highlights on the tour are the River Discovery Center, Market House Museum, Paducah Railroad Museum, as well as amazing murals on the flood walls along the Ohio River. This evening partake in the Drury’s Kickback Reception, which is a complete light meal. There are restaurants right by the hotel if that suites your fancy. 

Included Meals: Breakfast, Drury Kickback 

Hotel: Drury Inn 

Day 3 – Paducah to Hopkinsville, KY 

A fabulous Drury hot breakfast gets our day started right. Shortly after we leave, we enter the city of Mayfield. If that sounds familiar, you may remember it from the news. In December of 2021, this courageous community was hit by a devastating F5 tornado. The heart of the city was completely destroyed. We will take a few minutes to drive through and see how these proud and resilient Kentuckians are rebuilding and restoring their hometown. You’ve likely heard of Murray State University, especially if you follow college sports. Kentucky is big time college basketball and we get to view some of their iconic venues as we traverse the state. Leaving Murray, our route takes us by Kentucky Lake and over the famous Kentucky Dam. Hope you’re hungry for a great lunch in a classy vintage setting because that’s exactly what we find at Patti’s 1880’s Settlement in Grand Rivers. Departing, we journey the Land Between the Lakes, across the Cumberland River to Casey Jones Distillery. We are invited to a guided tour of this family-owned, attractive, and classy setting featuring cast strength bourbons and family recipe moonshines. You may want to clean your glasses before our next stop or you may think you’re at the Washington Monument. Nope! It’s the Jefferson Davis State Historic Site. Taking 16 years to complete and dedicated in 1974, it is the world’s tallest concrete obelisk at 351 feet high; and right here in little ole Fairview, KY. There is an elevator to the top and we will take time to explore the monument, wonderful museum, and lovely park on which it is located. Just up the road a few hundred yards is the Country Barn Garden & Farm Market, featuring amazing floral displays and great Amish-inspired food selections. We have time to explore and enjoy their offerings for supper. 

Included Meals: Breakfast, Lunch 

Hotel: Hampton Inn & Suites 

Day 4 – Hopkinsville to Bowling Green, KY 

Enjoy a convenient breakfast at the hotel. Departing Hopkinsville, we head due north along the Pennyrile Parkway to the Pond River Valley, where we connect with the Western Kentucky Pkwy through the rolling and forested hillsides to Central City. What’s so special about Central City? It is the hometown of Don & Phil Everly – the beloved Everly Brothers! Fond memories from our youth are captured in the Muhlenberg Music Museum and adjoining Dream Car Museum. The Everly Brothers were inducted into the Rock & Roll Hall of Fame in 1986, followed by induction into the Country Music HOF, as well as a Walk of Fame Star on Hollywood Boulevard. It all started here! Now, “All I Have To Do Is Dream!” Driving north from here we find Owensboro, KY on the banks of the Ohio River and the beautiful home of the Blue Grass Hall of Fame. Bluegrass is a truly American music style evolving over the last 75 years. This welcoming attraction takes us through the history of Blue Grass, the story of the Father of Bluegrass, Bill Monroe, and an amazing exhibit of Bluegrass instruments. Owensboro is famous for its BBQ, anchored by one of the best BBQ Restaurants in all of America, Moonlite Bar-B-Q – literally voted as one of the world’s happiest places! Trust us, after this visit, you will never forget one of the most incredible buffets you have ever experienced! Next is a sight you’ve never seen before and can only see here. Preparations for this sight started almost 300 years ago! We’ll get pictures of what’s believed to be the largest Sassafras Tree in the world, standing at over 100 ft tall and measuring 16 ft in circumference! We then turn back south to Bowling Green and the Railpark Museum, a beautiful historic passenger train depot. Next in store is a fascinating adventure – an underground boat tour of the Lost River Cave, a Kentucky Natural Wonder. Touch the cave’s limestone ceiling before the passage opens into an enormous cathedral like cavern. Enjoy the convenient Drury Inn Kickback or dinner on your own at restaurants near the hotel. 

Included Meals: Breakfast, Lunch, Drury Kickback 

Hotel: Drury Inn & Suites (2 Nights) 

Day 5 – Bowling Green area 

Get ready for a mammoth day after Drury’s hot breakfast bar. We’re headed to Mammoth Cave National Park! After a short but delightful drive into the wooded hill country that is home to “Cave Country” we will enjoy a guided cave tour like none other anywhere. We have chosen a tour that is most comfortable for all yet represents the best features of this grand phenomenon. If you’ve been here before, you will welcome the return, and if not, this is a bucket list experience for sure! We have ample time, so relax and enjoy this special Sunday morning. Nearby in sleepy Park City is the vintage Grand Victorian Inn. Karen is planning a “grand” home-cooked Sunday Dinner just for us! Next up could be a highlight for many of you: The National Corvette Museum. The first Corvette was created in 1953. The museum opened in 1994 and is the home to over 70 Corvettes displayed in periodic settings spanning the history of “America’s Sports Car.” 

Included Meals: Breakfast, Lunch, Drury Kickback 

Day 6 – Bowling Green to Berea, KY 

Eat hearty this morning and prepare for a very special day. Today, we make our way along the Cumberland Parkway over the rolling picturesque landscape of Central Kentucky to Russell Springs. You’ve probably never been to Russell Springs before, but after today you’ll never forget it. Here we will be met by hometown favorite son, Kevin Williams, of Gaither Vocal Band and Homecoming Videos and one of Nashville’s most requested guitar artist! Kevin is going to show us his hometown, Russell Springs where he grew up and remembers fondly. Along the way and throughout the morning Kevin will entertain us with music and stories in his genuine homespun, side-splitting manner. The morning will vanish and we’ll wonder where the time went. But we still have time for a hometown lunch, prepared by the “basement church ladies” of Kevin’s home church! What a unique, unforgettable backroads experience in the Bluegrass State. Departing Russell Springs, we enter Eastern Time Zone and Danville. Here we discover Constitutional Square, celebrated as the Birthplace of Kentucky, an attractive parklike exhibit revealing the early history of Kentucky. Danville sports a classic “hometown downtown.” You won’t want to ignore Burke’s Bakery. We’ll journey a few miles further to the little village of Berea for the evening. Dinner is served in a historic and elegant style at Boone Tavern, so named for its location on the Daniel Boone Trail. In continuous operation since 1909, Boone Tavern and Berea College are inextricably intertwined since the Tavern was built as the guest house for the College. Fine dining has brought Boone Tavern much of its international acclaim. Enjoy a relaxing and delightful evening! 

Included Meals: Breakfast, Lunch, Dinner 

Hotel: Fairfield Inn 

Day 7 – Berea to Corbin, KY 

Immediately following breakfast this morning, we are treated to a student guided tour of Berea College. One of the most unique colleges in America, all students cover their tuition and expenses by working in all capacities for the college or Boone Tavern. You will be delighted by this experience. Berea is definitely a center for arts. We’ll discover a number of those as we visit Old Towne Artisan Village featuring Weston Glass Blower, Weavers Studio, Top Drawer Gallery, Becky’s Breads, and many more. Continuing on the back road, we enter Renfro Valley where we discover the Kentucky Music Hall of Fame. This hallowed place honors Kentucky’s incredible performers, songwriters, broadcasters, comedians, and many others who have made significant contributions to the worldwide music industry. In addition to viewing the museum, we are treated to a Kentucky down-home lunch while we enjoy the music of some of these incredible performers. After checking into our hotel in Corbin, more excitement awaits us. We are doing supper at Harland Sanders Café. Yep! Colonel Sanders original location and the beginning of KFC! You’ll love the very friendly and informative exhibit telling the incredible success story of KFC. 

Included Meals: Breakfast, Lunch, Supper 

Hotel: Hampton Inn 

Day 8 – Corbin to Prestonsburg, KY 

We think you’ll sense the expectancy at breakfast as anticipation for this morning’s backroads journey builds. Beautiful scenery unfolds as we motor up the Cumberland Valley into the heart of Appalachia. Brunch is a bit early, but we just have to stop at The Pine Mountain Grill. True & pure backroads material is ahead. The little mining town of Jenkins welcomes us with open arms, and the pride of this untouched community is the David Zegeer Coal-Railroad Museum. Get the inside story of the glory days of mountain coal mining, clearly a world most of us never really understood…until now! This is an enriching experience. We now travel on to Pikeville, the stomping grounds of the Hatfield & McCoys, and the legendary saga of this famous and heralded mountain feud. This is where it all came to be. We get to be a part of it first hand! The locals here will spin their stories, share their culinary skills, and entertain us with their unforgettable mountain music. 

Included Meals: Breakfast, Brunch, Dinner 

Hotel: Comfort Suites

Day 9 – Prestonsburg to Lexington 

Did someone say music? Legendary music? Backroads? Wow! This is as backroads as it gets! Leaving the hotel, we take one side road after another as we wind our way into Butcher Holler. Heard of that before? If you saw the movie Coal Miner’s Daughter you have. It’s the amazing success story of one of Country Music’s most famous & legendary stars, Loretta Lynn. We are making our way to Van Lear, the mountain ‘holler’ and one room shack where she grew up. This is certainly a picture moment! We visit the Webb Grocery store, unofficial yet proud “visitor headquarters” of Loretta and Crystal Gayle (sister) memorabilia. We are treated to a genuine mountain lunch as we visit the Coal Miner’s Museum in Van Lear. This is a genuine, rare, once-in-a-lifetime experience. Don’t miss it! Leaving the core of Appalachia, we turn back east along Mountain Parkway towards Lexington. Shortly before Lexington, we discover an attractive and compelling place known as the Bluegrass Museum. Fits our theme well, right? This little spot brings the history and culture of Central Kentucky to light. Everything here has a unique story to tell about the people, events, and culture that shaped life among the Bluegrass. Proceeding on, we visit the girlhood home of Mary Todd Lincoln, one of America’s most fascinating first ladies. Then just a couple blocks away, is possibly ground zero for college basketball. No place is more famous or hallowed in all of college basketball history than Rupp Arena on the University of Kentucky campus. 

Included Meals: Breakfast, Lunch 

Hotel: Staybridge Suites (2 Nights) 

Day 10 – Lexington area 

We are in the very heart of thoroughbred horse country. It is only fitting that we take the morning to explore the horse farms this iconic bluegrass region is so famous for. Enjoy this relaxing, informative, and beautiful experience as we make or way among the graceful, fence lined pasture land. Lunch is on your own among the homespun eateries of the quaint little village of Midway. The capitol of Kentucky is Frankfort, so it’s fitting that we visit there as well. We’ll see the old historic capitol building as well as the beautiful current one. And no visit to Frankfort is complete without stopping at Rebecca Ruth Candy Company. Treats are in order! We return to the Staybridge Suites where a pizza party is planned in the comfort and convenience of our hotel. 

Included Meals: Breakfast, Treat, Dinner 

Day 11 – Lexington to Bardstown 

We’ll get on the road first thing this morning, but don’t get too settled in as we’ll be stopping soon at a really fun place known as Nostalgia Station. This Ma & Pa shop, located in a 1911 Louisville & Nashville RR Passenger Station, is full of fun childhood toy and train memories. Many of them are for sale as well. A true “bucket list” experience is next on the docket. My Old Kentucky Home! The 200-year-old mansion & plantation that inspired Stephen Foster to write the famous song we all sang as kids, “My Old Kentucky Home.” This is Kentucky!!! Included lunch is served in the fun, historic surroundings of Old Talbott Tavern. Next we’ll make a brief stop at the Oscar Getz Museum of Whiskey History, displaying a 50 year collection of rare American whiskey artifacts from pre-colonial days till after Prohibition. Then Bardstown Museum and Village features one of the top ranked Civil War museums in the country. It houses many rare and authentic artifacts of the union and confederate armies. Old Bardstown Village is made up of ten log structures, all dating back 200 years to Daniel Boone days in this county. We’ll check into our hotel before departing on another grand adventure: dinner is elegantly served on My Old Kentucky Dinner Train. Dine in 5-Star style as we ride the rails in classic 50’s memorable manner through the rolling Kentucky hill country. What an incredible day this has been! 

Included Meals: Breakfast, Lunch, 5-Star Dinner Train 

Hotel: Holiday Inn Express 

Day 12 – Bardstown to Louisville, KY 

Our first stop, shortly after we depart, is Abe Lincoln’s Boyhood Home site on Knob Creek. This is where Abe lived from the ages of two to six. Then we go just 15 minutes away to Abe Lincoln’s Birthplace location, which is now designated a National Park. Both are hallowed, historic, beautiful spots. We have found one of the most attractive and informative exhibits of Abe Lincoln’s life and career right on the charming village square in Hodgensville. We will feel like we were right there during many of the historic moments of Abe’s life. Hometown lunch today at the Back Home Café in Elizabethtown. Next we have made special arrangements for a private showing at one of the most amazing collection of vintage automobiles at Swopes Cars of Yesteryear. They are opening on Sunday just for our group! We will be wrapping up our Kentucky experience at none other than possibly its most famous venue, Churchill Downs and the Kentucky Derby Museum. There is a buzz of activity and excitement around here at this time since we are less than two weeks from the running of the Kentucky Derby. Accommodations this evening is the comfortable Drury Inn. 

Included Meals: Breakfast, Lunch, Drury Kickback 

Hotel: Drury Inn & Suites 

Day 13 – Louisville to LeClaire, IA 

Another fabulous Drury breakfast prepares us to start our journey home. We exit Kentucky, crossing beautiful Ohio into Indiana. It’s too early for lunch, but never wanting to pass an opportunity, we stop for the ultimate deli experience at Shapiro’s Deli in downtown Indianapolis. The treat of your choice is on us! Indulge! Afterwards we will swing by the “Brickyard,” the Indianapolis Motor Speedway, just for a quick peek before we’re on the road again. Our farewell dinner has been arranged at the Granddaddy of all salad bars, The Packing House in Galesburg IL. Literally 50 feet after we cross into Iowa, we find our resting place for the evening. Our final night’s lodging of the tour is beautifully located on the banks of the Mighty Mississippi! 

Included Meals: Breakfast, Brunch Treat, Dinner 

Hotel: Holiday Inn Express 

Day 14 – LeClaire to Home 

Have breakfast at the hotel before starting the final leg of our amazing Backroads & Bluegrass journey. You now know & appreciate more about Kentucky than you could have ever imagined! 

Included Meals: Breakfast