Harley Davidson Road Trips in Kentucky

Travels with Harley

Last week I talked about a few Harley Davidson road trips that were closer to home, which really made me thirsty for Harley Davidson road trips of our own. Maybe a three-day weekend where Jim and I could travel a bit further from Washington, Missouri, but still be close enough to get back without having to rush. With that being said, I started checking out some Harley Davidson road trips in Kentucky, which isn’t too far from us, that I would sure like to venture out on.

Travels with Harley

Eastern Kentucky is known for its great Harley Davidson road trips and the Hillbilly Ridge, or the Newfoundland-Elliottville route, is certainly no exception. According to what the other riders have said it’s what Eastern Kentucky Harley Davidson road trips used to be like. It’s kind of scary with its narrow twists and turns. The route actually runs along the ridge, hence the name, and has some fantastic views, however, according to one rider you don’t dare take your eyes off the road for very long!


Known as the Bluegrass State, Kentucky has some excellent Harley Davidson road trips that will take you through the Appalachian Mountains into the Kentucky River region towards the north and some scenic water land in the west. Because it’s the home of the Kentucky Derby, there are some excellent historical places to visit including the Trail of Tears and the Underground Railroad.

Travels with Harley

Fat Daddy’s Little Country Dragon, don’t you just love the name, has lots of curves and bends while giving you a glimpse of Kentucky’s sweeping hills. Perfect for beginners to advanced riders, the best time to take this route is in the fall. The roads are great, have been repaved, and include everything from flats to straights. You won’t find many places to eat along the way, but once you get to your destination you will be met with the Fat Daddy’s Bar and Grill in Land Between the Lakes, which is actually in Tennessee. Located in what is known as the Little Keys in Tennessee, it is the place to stop, as it is right on the edge of Kentucky Lake. The shrimp jammers sound yummy, as does the Tennessee River Dawg. I know that we will be stopping here when we venture out on one of our many Harley Davidson road trips.


Route 32 is another great Harley Davidson road trips in Kentucky. The Morehead to Louisa ride features great views of the mountains, especially during the fall and spring. Once you get to Lawrence County, you are right alongside Yatesville Lake. The twisty roads take you through gorgeous Eastern Kentucky and are well maintained. I like the selection of amenities along the way as well.

Travels with Harley

According to one rider the B & C Market, located in Blaine, is a must. Apparently, Louisa has quite a few cafes including the Down Home Grill that used to be called Lisa’s Front Porch. The menu is loaded with feel good favorites including homemade chicken and dumplings.

If Jim and I had the time, we would retire and be on permanent Harley Davidson road trips!