Day 3: Middlesboro to Harlan, KY

It was going to be another hot day today, I could already feel the humidity. It was already late in the morning when we got over to Sonic’s for a late breakfast and to figure out where we were riding today. After about an hour we had a route and we took off on 58 for Virginia.



Welcome to Virginia

The closest road to cross the mountains in to Kentucky on the map was 797, but when we got there we realized that this road wasn’t even paved. Great for us actually, except I couldn’t ride this road. I rode a portion of it and then stopped and sent Mike up to investigate the rest. The road was steep and with many big rocks. Mike came back down with bad news, it only got rougher and steeper ahead.



797 Runs between Kentucky and Virginia and it's dirt



Mike heading up 797 to investigate the riding conditions ahead

I wasn’t able to ride a road like that so we turned around and continued to the next road that crossed the mountains which was 421, a major state route. As we cruised along 421, I noticed a river and a bridge to the right, so we turned around to check it out. It was pretty cool and we ended up hanging out there for a while. Even though it was located next to a major road, once down there the road above seemed miles away.



A few minutes later he was back, too rough, we had to go back

I wasn’t able to ride a road like that so we turned around and continued to the next road that crossed the mountains which was 421, a major state route. As we cruised along 421, I noticed a river and a bridge to the right, so we turned around to check it out. It was pretty cool and we ended up hanging out there for a while. Even though it was located next to a major road, once down there the road above seemed miles away.



A hidden river and bridge



My number #1 reason for riding a dual sport, it can go anywhere



Clear water



Mike found some coal



Looking for treasure



This was one of my favorite spots on this trip

We stopped for lunch in Harlan, KY at a Wendy’s and continued though the nice twisties along 421. The road that peaked our interest while looking at the map this morning was KY-1679, also called the Little Shepherd Trail, a narrow paved scenic road with turns and twists and some steep parts that runs atop Pine Mountain. We went to check it out.



High-lighted in yellow: Little Shepherd Trail running left to right on the map

The pavement was very bumpy and broken up in places, not a road I’d ride a sport bike on. I was hoping I wouldn’t find any vehicles going the other way in the corners since this road is only as wide as one car. But there were no cars on this road at all. It took a while to get thought it.



View from the Little Shepherd Trail



Nice cliffs and rocks along the trail



A narrow road with some steep/tight turns



No guard rails here

Then we came to a fork in the road and unfortunately even with our GPS’s we didn’t know that we should have stayed to the left to get down from the mountain on the other side, since that’s where we were planning on going next. Instead we came down on 2010, very twisty and steep but wider road.

So we were stuck on the wrong side of the mountain now. It was getting late so we headed north, looking at the next few road on our route and realized we couldn’t get to where we wanted to go today it was already too late and the sun was already heading for the horizon. We didn’t want to get stuck on the bikes in the dark so we headed back to Harlan, KY to find a motel room, same town we had lunch at today. We would have to continue our route tomorrow since there were some dirt roads that we still wanted to ride.



Mount Aire motel in Harlan, KY looks nice but looks can be deceiving

For $66 a night we found a neat looking motel, so we grabbed a room. When we rode back around to our room we found some nasty looking old section of the building, not at all like the new part that was facing the road. We opened the room door and it was pretty nasty inside also, old and run down and smelly. We went to get out money back, there was a Holiday Inn Express down the road that looked nice also, but apparently the policy was that no one can get their money back for any reason. So since we were forced to stay there for the night, we paid extra for a nicer room in the newer section up front, so now we were unhappy and paying $77. What a scam. I can’t recommend a place like that, looks very nice from the outside but once they have your money you’re stuck. For dinner we walked down the road to the Dairy Hut for a hamburger and chili.



Dinner at the Dairy Hut in Harlan, KY, hamburger for Mike and chili for me