Kentucky: Wet Roads Through Dry Counties to The Cumberland Gap

80% chance of rain!

That’s what I would be riding in, and since there was one more trail that I wanted to walk, I was up and out of my room early. The trail led me to The Towers overlook but since it was a misty morning, the views were limited.  Even still, my walk into the woods was intriguing, even mysterious, as I had no idea what was around the curve in the trail.




Once back from my walk, I hit the dining room for breakfast and just as I finished and walked outside, the rain began, although lightly.  The housekeeping staff gave me some extra plastic bags (to pack wet things in later) and I left the Breaks.

With each mile, the rain came harder, but it wasn’t so hard that I felt the need to pull over.  I rode on some twisty, turning, beautiful roads.  Oh how I wished I was riding them on a sunny day!  The rain seemed to emphasize the poverty in some of the very small, remote communities that I rode through.  Signs of support (and opposition) to the coal industry were everywhere.

As I rode, I kept wishing I could stop to take photos, but the rain kept coming down. I rode between rocky, tree covered hills on my right, and river beds and ravines on my left.  Simply gorgeous!  The weather forced me to rearrange my route slightly, and at one point, I turned around and out of Kingdom Come State Park when I hit an unpaved, incredibly hilly road called the Little Shepherd Trail.

My goal, since I was riding alone, was to stay safe,  be smart, and have a different outcome from my ride last fall.  In other words, arrive home safely.  Even still, I was disappointed that I would not be able to explore the park, named after a Civil War novel, “The Little Shepherd of Kingdom Come,” by Kentucky author John Fox Jr.  Kingdom Come State Park preserves 1,283 acres of unspoiled wilderness.

At one point I was forced to stop for road work.  A 25 minute stop.  On a steep hill.  Holding onto the brake.  Unable to go forward, backward, or to get off the bike, I watched crews work to straighten out an incredibly curvy road through a tiny little hill town.  Phew!  My guess it will take years to finish that road.

After about 4 hours, the rain slowed and finally stopped, and I stopped for gas.  Since I’m not able to share photos from the ride, I thought you might want to see the result of the ride on my pretty bike.


My plan was to stay at Pine Mountain State Park, but when I got there, the lodge was booked.  It was time to ride on, explore the surrounding area, and think about where to stay for the night.

As an aside, by now I’d also learned that not only were the State Parks in Kentucky alcohol free, but the entire part of the state in which I was traveling was DRY.  According to Wikipedia, “the alcohol laws of Kentucky lead to a confusing patchwork of counties that are dry (prohibiting all sale of alcoholic beverages), wet (permitting full retail sales), and moist (occupying a middle group between the two)”.

Of the 120 counties in Kentucky, 55 are dry … and those are the ones I was riding through.

When I walked into the Visitors Center at Cumberland Gap National HistoricalPark, I was greeted by a wonderful Brit who not only gave me information about the park, but also a list of nearby hotels, and directions to Pappy’s Beer & Wine.  In order to get to Pappy’s, I had to ride through the very cool Cumberland Gap Tunnel, out of the state of Kentucky, into the state of Tennessee, and then back into Kentucky with a bottle of red wine safely tucked into my saddle bag.


(photo credit:


After securing a hotel room for the night, I rode to the top of the Cumberland Gap, “the first great gateway to the west”, where the buffalo, the Native American, the longhunter, the pioneer all traveled this route through the mountains into the wilderness of Kentucky.  For many, it was the way to a new life in the frontier wilderness. Through the Cumberland Gap, a natural passage through the forbidding Allegheny Mountains, passed the Wilderness Road.  Hacked out in 1775 into by a party led by Daniel Boone, this road was one of the main arteries used by the settlers who occupied the region between the Appalachians and the Mississippi River (

This cabin, a replica of an original pioneer cabin, stands near the Visitors Center.



The ride to the top was one 180 degree turn after another, with each turn an elevation change.  Thank goodness there was little traffic as I was challenged by that ride.  While my photos from the top of the Gap reveal the continued overcast, foggy day, I thought you’d appreciate seeing one that I downloaded.  The first are mine, the last is not.


As I stood there, looking at that beautiful scene, the mists and clouds rolled right over me.




This is what I hope to see when I return on a beautiful day.


I spent two hours in this national historical park, but could have spent more.  So much history, so much to learn! As evening approached, I checked into my hotel and found a wonderful locally owned restaurant in downtown, historic Middlesboro.  A delicious meal at Shades Coffeeshop was followed by a lovely plastic cup of wine in my hotel room surrounded by drying bike gear.  Ah, life is good!

And tomorrow, my Kentucky adventure continues!

34 thoughts on “Kentucky: Wet Roads Through Dry Counties to The Cumberland Gap

  1. Awesome!!! Your “baby” is doing well by you!! Thanks so much for taking us along…..your journey thus far is gorgeous. My local curvy hilly roads have provided much riding enjoyment this year…close to home. A relatively quiet summer. Life IS good!!! Hugs and “ride invisible”…………………….

  2. I enjoyed this travelogue so very much. It warms my heart that you are out on your bike, doing your thing, being yourself again with such an upset in your past. You are a strong woman.

    The second photo is my fave this time, because of the subject. The trail promises something around the bend, if only I’ll follow it. I love that siren call!

    The rain adds a delicious atmosphere, despite blocking all the best views. Thanks for all the interesting information. I didn’t know anything about the Cumberland Gap, but oh, if some of the rocks could talk around there; what wonderful stories we would hear. I can’t help but think of Bruce’s Hack of a Day post when I read that Daniel Boone “hacked” through the gap.

    Love your adventure to go get alcohol! I can’t even tell you how perfectly I relate to that, ha ha. A glass of wine means so much to me at the end of a day, it’s worth some trouble making it happen. I’m going to look up photos of your mountain ride to the vista. If there is any way to see that twisty road through the trees, I’ll bet it looks impressive.

    • Crystal, thank you so much for reading the entire post. That means alot to me. Truly! I know that it was a long one, but I wanted to share the day.
      Someday I’ll go back and see those roads again!

  3. I love your posts Laurie I feel like I took the trip with you. I know what you mean about the rain accentuating the depressed areas of your trip. I encounter the same things in upstate NY in the north east part where GE had plants and closed them down and decimated entire towns as well as the paper mills closing down. I think GE also closed a diesel locomotive plant in western NY and killed that area along with Corning glass works downsizing. In any case I would have had to make a beer run just like your wine run if I was in a dry town 🙂

    • You DO get it! I know that those GE closings, like the auto industry in Detroit, severly impacted the economy and the self esteem of individuals and communities.
      Thank goodness for Pappy’s! I would have gotten beer, but I didn’t have room in the saddle bag. You should have seem me … judging the space in the saddle bags, heating / cooling, bottle opening, mixers … wine ultiately won the day, but I sure missed my cold end of the ride beer!

  4. Glad you are out on the bike again and taking some vacation– and not just riding but taking time for walks. We have to get back to Breaks Interstate PKU and spend some time. Beautiful place. By the way there are two places on Pennsylvania that claim to have the biggest canyon in the East- by what measure? Loved the photos,esp. The first with fence and mountains, but I’m also partial to cut old cabin photos :). Too bad the weather shut you down in Cumberland Gap.

    • Chuck!! I thought of you many times while riding … than you so much for reading this post. I really enjoyed Kentucky. The history, the State Parks, the beauty, and the history. But no end of the day beer!
      I’ll need to check out the Pennsylvania canyons!

  5. Sqeeeeee!! My favourite most loved Laurie Buchwald photo of all time!! Still my favourite!!

    The lesson learned from this trip has to be ‘check out the dry/wet stature of all future planned trips before commencing – thusly ensuring certain comestibles be carried with 🙂 And maybe even a carefully packed wine glass too – it’s just not the same out of plastic.

    I’ve heard of the Cumberland Gap – maybe in a folk song? – as kids we loved Daniel Boone and Davy Crockett too – my brother had a coonskin hat ……… I didn’t I ‘was a girl’…….. 😦

    I can see how you would yearn for the sun to shine, that mist sure looks heavy. So beautiful despite the weather and the bike still looks so red and shiny despite the rain and mud. And the close up of the pioneer cabin – just gorgeous!

    • Oh you made me laugh with the “checking out the stature before commencing” 🙂 I have learned my lesson!!
      Thank you for reading the whole post (I know it was a long one).
      While the rain changed the plan a bit, I still enjoyed the ride. The next day offered much better weather, thankfully.
      It’s alwasy so great to hear from you!

  6. The bike is still pretty, even after the rain. Kentucky is a beautiful state…I’ve ridden through. I wish it would have been better weather for you, but it appears you enjoyed the ride nonetheless. You got some fabulous photos from the trip.

    • I did enjoy the ride, even with the ride. It’s all a part of it, isn’t it?
      I look forward to the trip back … and will be prepared for the “dry” parts next time 🙂

    • We always joke that once wet, you really can’t get any wetter 🙂
      And as long as I can see the road, I’m game (most of the time – ha!)

  7. I very much enjoyed this post, including the photos. I lived in western Oregon and Washington for twenty-five years (ten in Oregon, fifteen in Washington). I love rainy vistas!

    • You DO know all about the rain then, don’t you?
      Believe it or not I’ve not been to Oregon!! I have a friend who just bicycled down the entire Pacific Coast and his photos from Oregon made me want to go so badly.
      Glad you enjoyed the post!

  8. Some great, very descriptive writing. I almost feel like I was riding with you, complaining all the while about the rain and my wet gear. Aren’t you happy you went without me?

Because Boomdee dared me: Lay a little sugar on me :-)

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