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

Day 2: Mount Vernon to Middlesboro, KY

We were looking forward to camping for the rest of the trip, but since I have never “toured” on the XT225 before, I didn’t know how much weight I’d be comfortable carrying on this tiny bike. After taking some time and loading up the two bikes with all the camping gear and stuff needed for the next few days I unfortunately realized that with so much weight on the back of my bike, the XT was all the sudden very top heavy and not very stable, especially for dirt ridding. If I had some saddlebags, and was able to distribute the weight down low, I think it would have been fine, but all the weight on the back seat and on the rack behind the bike was too much. Funny how I can carry 5 times that amount on my ST3 just because it’s a bigger and heavier bike, twice as heavy than my XT.



Doesn't seem like so much stuff, but my bike was very top heavy with all this stuff on the back

We abandoned the camping idea, left all the camping gear in the truck and decided we’d just find motels to stay at. We went off to have breakfast while we contemplated what today’s route should be. We kind of wanted to end up for the night around the Tennessee border.

We headed south from Mount Vernon, a little later we found a road we wanted to ride, but it dead ended at a lake, so we kept riding east on 80 finally finding some nice dirt/gravel roads that ran through the forest. This was great so far, the road was good quality, a gravel/dirt mix and we were even traveling in the right direction too. Then unexpectedly we arrived at a gate that had the rest of the road closed off.



Nice dirt road through the forest



We found some arches on this road



Mike having fun with the arches



There was another smaller dirt road that went off to the right that we couldn’t find on our GPS’s so we decided to try it anyway and see where it went since we’ve come and long way and didn’t want to turn around. This was a nice twisty narrow dirt forest road, but then after about 8 minutes it ended and we had to turn around and go where we came from.

My bike still felt strange the whole time, so finally I stopped and moved the luggage bag closer to me and let some air out of the tires and finally it felt good again. I should have done that a couple of hours ago.

It was already the afternoon, so in order to get to where we wanted to go, we’d have to stick to paved roads to make up some time. Today was another hot and humid day, and at some point the clouds moved in and we got rained on but only for about 10 minutes, we didn’t even bother to pull over. In Barbourville, KY we stopped at a Subway for a late lunch. The Subway was surprisingly nice, almost fancy, with a crystal chandelier, must have been something else before. This whole town was actually very nice. I was still hoping to make it to Cumberland Gap today, but the only way we could do that is to switch from the little paved roads to a larger paved road that would get us there directly. We jumped on 25E and headed to Middlesboro, KY, where we wanted to find a motel room for the night. There was still plenty of daylight left so we decided to explore the area.



You can see the Cumberland Gap Tunnel behind Mike, it's 4,600 feet long and has 4 lanes



Welcome to Tennessee

Then we went up to the Cumberland Gap National Historic Park. Formed by wind and water, Cumberland Gap is break in the Appalachian Mountain chain. Starting at the visitor center, the 4 mile long Skyland Road takes you up the mountain to the Pinnacle Overlook (elevation 2,440 feet) for an amazing view of Kentucky, Virginia, and Tennessee. The road is very twisty, narrow and steep at times. So far this was the steepest/tightest paved road that I’ve ever rode on the XT.



My XT taking a nap mid-turn

In first gear the bike was screaming like crazy, in second gear it wasn’t pulling hard enough on the steep road but at least it wasn’t as loud. I stayed in second most of the time but then I came upon a really steep and tight right hander, just as I started to approach the turn staying really close to the inside of the turn since the cars coming down the mountain were crossing the double yellow, I realized I needed more power, I downshifted in to first gear and instead of moving forward, the bike slowed way down, pretty much stopped, then it wobbled, I tried to put my foot down, but the road was so banked that I wasn’t able to reach the ground and fell right over in the corner.




Low air pressure in knobbie tires + very twisty road + underpowered bike = an embarrassing moment

Gas started to pour out of the gas tank, I tried to pick the bike up but at that angle, I couldn’t do it. A few minutes later two cars came by and two guys helped me pick the bike up. It didn’t want to start at first but finally it roared back to life and I was on my way to the Pinnacle overlook. The only scratch on the bike was on the right brush guard. Mike was wondering why it took me so long to get up there.




Skyland Road going up to the Pinnacle Overlook



Many tight turns, Mapquest map above, they call this road Pinnacle Road, and it's misspelled "Pinacle" it's really Skyland Road



Pinnacle Overlook



View from the Pinnacle Overlook





Heading back down the mountain




Back in Kentucky on the other side of Cumberland Gap Tunnel

The view from the top was great. We rode back to down to Middlesboro, the first motel we saw Parkview Motel, turned out to be a dump, we then found The Downtown Inn & Suites on Cumberland Ave which was much nicer and only $60 a night. There was no restaurants within walking distance and by the time we showered it was too late to eat anyway.

Day 1: Mount Vernon, KY

We finished up the miles in the early morning and started looking for a motel in central KY. After finding an appropriate motel where they didn’t mind us leaving truck and trailer for a few days in their parking lot, we unloaded the bikes and we took a ride toward the Daniel Boone National Forest.



This Super Sleep Inn motel parking lot was empty this early on a Saturday

Today was just a day ride, we would be returning here tonight to the Super Sleep Inn in Mount Vernon, KY. This was the cheapest room we could find in this area and for a $45 room, it wasn’t bad at all, the only thing that could have been a little bit better was the shower head.



It was a hot and humid day, temps in the upper 80’s. After riding down many paved roads, some through the forest and some through residential areas, we finally found a nice dirt forest road. There were some hills, some gravel, some dirt, a bit of rocks and a few water crossings.



Nice twisty dirt road through Daniel Boone N.F.







Small splash

My pathetic water crossing, the water wasn't very deep. Mike forgot to being his camera, so I gave him mine to take this picture, I didn't know there would be much better water crossings further down the road.





Big splash

Towards the end of the day while riding through Livingston, KY, we pulled over at Lil’s for dinner. It wasn’t the home cookin’ we were expecting in a small Kentucky town. It was very much like fast food, just made a bit slower. Our dinner consisted off a chilly dog, chicken strips, curly fries and a milk shake. It was good. The sun was setting so we headed for the Super Sleep Inn, since we didn’t have a good night’s sleep last night and we were beat.



In Livingston, KY outside of Lil's Restaurant



Dinner: Mike's Chili dog, my chicken strips and fries for sharing



Inside Lil's Restaurant

Heading down to Kentucky

The plan for this trip was that there was no plan. Even though a 4-day ride was on the schedule for a couple of months, we just didn’t have enough time to figure out any good dirt roads to ride in Kentucky prior to this trip. We chose Kentucky because of the large area that the Daniel Boone National Forest occupies and where there is forest, there are forest roads.

The Daniel Boone National Forest runs from the northern to the southern part of the state and is generally rugged and characterized by steep slopes, sandstone arches, and canyon-like hollows and valleys. It encompasses over 699,575 acres of land managed by the USDA Forest Service.



Early Friday evening with the bikes loaded on the trailer, we headed for Kentucky. The traffic was moving slow and the construction on I-294/80/65 wasn’t helping us to get there any faster. A couple hours later in Indiana we stopped to grab some dinner. A couple more hours later we pulled over, Mike inflated the air mattress in the back of the 4runner and we decided to get some shut eye, we were both too tired to drive after a full day at work.

Illinois is getting another transplant

This was a very busy weekend because this weekend Mike was moving to Chicagoland. On Friday night I flew to New Orleans, Louisiana. On Saturday I helped Mike finish packing and we also visited with his friends and family for a bit. And today we drove to Chicago with all his stuff.



Mike's favorite donut shop in Lafayette, LA



My donut holes



Mike's Toyota with all his stuff outside of Raising Cane's Chicken Fingers in Mississippi



Our lunch, the best chicken fingers in the world



So moist



And the secret sauce

We left Lafayette, LA today about 7:30AM and after driving just shy of 1,000 miles we made it to Chicago around 11PM.