Moonshiner 28 and Tail of the Dragon 2018

On Tuesday, July 17th, 2018, an adventure began. Two men left Milwaukee, WI after work and saying goodbye to their families. One of them was a veteran roadtripper and Iron Butt rider, the other had never gone 300 miles in a day. Before they returned home, they would join two other riders, survive mechanical failures, rain, tornadoes, and buffalo.

Day 1

Day 1 began simply. I had convinced a former co-worker, Wyatt, that it was in his best interest to accompany me to the Tail of the Dragon and Moonshiner 28 for a 5 day trip. Wyatt was in the middle of changing jobs, so I didn’t give it much of a chance that he’d come. I had three veteran rider friends whom I thought would certainly come drop out due to work and health issues. As I mention in Planning Group Rides, the circle-back is key – keep pestering people to see who’s coming.

I met Wyatt in South Milwaukee and we rode to Lisle, IL to meet up with Harley Mark. You may remember him from my last trip to the dragon’s tail. We did this to get around Chicago and try to make the next day an easier trip miles-wise. I’ve never had rider friends not get along, but just in case, we went to a nearby watering hole to get this new friendship started.

Maybe it’s bikers, or maybe it’s just decent people, but despite not having seen Harley Mark for two years, it was no big deal.

Day 2

We set out with the goal of Maryville, TN – within striking distance of the tail of the dragon, some 577 miles. “Today is the day we earn it“, I told everyone. Someone forgot their new Harley gloves at the gas station and immediately started joking about being “that guy”. We started working on nicknames for the new rider involving gloves and u-turns. Our second mishap involved me fat-fingering google maps and heading to Kankakee, IL instead. I always think of Willie Nelson’s “City of New Orleans” song when I go by. Anyway, we went a little out of our way and this should serve as reminder that letting google think for you comes with hazards. We got back on track and headed towards Indianapolis.

When leading, I (obviously) check my mirrors constantly for the state of traffic and my riding crew. I also gawk, though, and sing along to music. Imagine my surprise when Wyatt comes cruising up to tell us to pull over. He pointed down and his bike was… missing something. His right saddlebag had come off on I-65. Shit.

When it comes to vacation, I’m an optimist. I figured we’ll recover the bag, ride back to the Harley dealer we’d seen 10mi back or so, and have lunch while they fixed it. Not so. Keep in mind, at 75mph by the time something happens, and then you get your group’s attention, more than a mile may have gone by and it was a busy day. As I made a freeway loop from +1 exit to -1 exit from the accident, I found not a Whiskey Amber saddlebag but debris from what had once been a bag. So we road back to see if there was any salvage.

Miraculously, we recovered: a phone bent in half, his ID, his cash, his credit cards, and rain gear. All would come in handy in the future.

As we talked Wyatt into continuing on the trip, we noticed that his left saddlebag was also in danger of falling! We fixed the pins and set out in search of food. I secretly began thinking of nicknames involving lost saddlebags and gloves…

iPhones do not stand up well to semi trucks

We had all agreed to completely wing it on this trip in terms of food and sleep. One of the great joys of road trips is the random discoveries you make. Looking at a list of nearby restaurants and craving Mexican food, I led to us to “LA Cafe”. It wasn’t Mexican. I peeked in and the hostess saw me and asked “Are you looking for the cycle shop around the corner?” Huh? Looking around, I saw my mistake:


It was a biker bar. Not “The Cafe”, but “The LA Cycle Cafe“. Nice random find for bikers on the road! Good food too!

Note the missing right saddlebag on the middle hog…

We found a Verizon store and got Wyatt a new phone. We hit the road. Indiana is, honestly, my least favorite state to ride through. It’s just as boring as Illinoise, but with the addition of (in my opinion) some of the worst drivers east of the rockies and the worst roads. I-65 was, naturally, completely closed north of the city (as it has been on and off for years) which made the I-465 a hot stop-and-go mess. Still better than a day at work.

As I mentioned, the goal was a 577 mile day ending in or around Maryville, TN. By the time we got just around Lexington, KY Wyatt was showing signs of serious fatigue. This was a pretty eventful first roadtrip day for anyone, so we got rooms and crashed right away. There was a “bourbon bar and grill” on the grounds, and a classic car show going on in the parking lot. We did all right.

Day 3

We were miles from the dragon, but got up early and ready to rock. I had previously arranged to meet Wingnut Dave right at the mouth of the dragon. Wingnut Dave would be riding up from his new place in Georgia, and you may remember him from my Bun Burner Gold trip. Maybe it’s bikers, or maybe it’s just decent people, but despite not having seen Wingnut Dave for a year, it was no big deal. We picked up where we left off.

While waiting in the parking lot at 129 Harley near the West end of the tail of the dragon, I had the first of several fortuitous meetings. I saw two Harleys with 3 digit stickers on their saddlebags. Loaded for camping. Paper directions clipped to their bars. Holy shit! The Hoka Hey is going on right now and did they make this part of the route? Sure enough, I asked and they were two patch holding brothers from an Arizona MC on the Hoka Hey. I didn’t take pics of them or their bikes out of respect, but it was amazing to see a small part of something I’ve been reading about for so long out in the world. The fact that I happened to be wearing my Hoka Hey tanktop that day made me me smile.

We got through the tail of the dragon and regrouped on the other side. I had planned to ride US 129 West to East and East to West, but they were mowing the entire 11 miles and blowing grass all over the road. In my experience riding on grass is like riding on slick snot, so we instead headed to the Moonshiner 28. Not before I met two more Hoka Hey riders, though. One of them saw my shirt and said “Yo! Yo! Yo!” and I enjoyed the hell out of that. See my future article: “Some Day, Hoka Hey!” Again, I didn’t ask for pics out of respect for their time and the vision quest they were on.


We started South Carolina 28 right at the Deal’s Gap Motorcycle Resort. While I don’t think there’s a single turn as difficult as the switchbacks in the dragon, it’s 103 miles and still very technical. There are parts that are a straight 55mph road, and parts where the road narrows viciously and you’re likely to meet camper trailers in the worst turns. This was the most important part of the trip for me, since I got rained out last year. It did not disappoint. Not only was the riding amazing, but it’s right through an incredible national park with glorious scenery and waterfalls throughout. This is a magical place worth visiting via any transportation.



SC 28 ends in Walhalla. From there, my plan was to see an Oscar Blue’s brewery outpost there, and find a place to stay. Oscar Blue’s did not offer tours, but otherwise was close to what I expected. Tons of taps, a band playing, a custom food truck and of course beers to go.

I found beds that night by randomly looking at a map and picking a place that didn’t sound like a chain. I called the Pines Country Inn and asked what they had. The answer? Mountain views, a bonfire, and a country breakfast cooked by the proprietor’s mother. Inexpensive, local, charming, and awesome: this is the kind of find you hope for when traveling without firm plans.

While they gave us wood, it was wet and starting a fire would be up to us. I was glad I carry a hand axe, a tactical flashlight, emergency fire starting materials, and thermacell with me when I travel. My “just in case we get stranded sleeping at a rest area” kit came in handy.

Campfire Talk

Finally, on day 3, we had gotten some sleep the night before and there was enough distance from The Saddlebag Incident that everyone was ready to open up and talk in good spirits. Wyatt was named “Lefty” for having only his left saddlebag and I think that’s going to stick.

It’s an important thing for men to be able to talk with other men. We live in a world where men of a certain age still think , or at least were raised to think, that honesty and vulnerability are signs of weakness. This is not to say that any friendly rider wouldn’t be welcome on a trip with me. Sometimes it just takes hundreds of miles and a little adversity to feel comfortable with people. The bond shared by band members, sports teams, or any other group “on the road with a mission” must be similar.

We talked. We talked about our second lucky find in this B&B, about my hilarious packing list that included a packing list and a tactical flashlight.We talked about Wyatt’s newfound understanding of the freedom of the open road. Other stuff. We stayed up too late and drank too much. It was perfect.

Day 4

My goal for the next day was to start working slowly towards home. A couple of the guys had not seen the Cumberland Gap Tunnel on TN 25E, so I wanted to hit that and then do the Buffalo Trace Distillery tour before stopping at my usual haunt in Shelbyville. We knew there were big storms coming but figured we could beat them. We were wrong.

As we reached Southern Lexington, it was clear that the horizon had turned into a hot mess of weather. Wingnut Dave pulled me over to talk some sense into me. Harley Mark pointed out that he’d seen a Hooters sign a few miles back and the radar seemed to say we could wait it out. We headed back and barely got inside before the sky unleashed hell. Buffalo Trace would have to wait. We spent hours at the restaurant as the weather winded down, and the parade of emergency vehicles ran around afterwards. We bought bourbon nearby. We made hotel reservations nearby.

As we rode towards the hotel, I noticed something. Light pollution is so jarringly ever-present in our cities today that you notice it when every house and street lamp is dark. I knew before we got there the hotel would not have power. I was right. We “had rooms” reserved online that they could not let us in to until they at least had power. We settled in, opened a deck of cards, I started sewing on my Moonshiner 28 patch (the shittiest stitching I’ve ever done), and opened the day’s haul of bourbon. It wasn’t long before I pointed out “Guys, even if power never comes back we can’t possibly ride out of here…”; a bottle of Buffalo Trace was already looking badly used. We were committed. Not long after power came back we had another surprise: a tornado had been spotted a mile away and the hotel manager was herding everyone into the stairwells. So here we are, four drunk bikers passing around bourbon along with crying children and all kinds of families. Eventually the coast was clear, we took a dip in the pool, and then settled into the hotel lobby for cards and more bourbon. We talked again. We stayed up too late. We drank too much. It was perfect.

Day 5

The morning of Day 5 we parted ways with Wingnut Dave, heading to Buffalo Trace for the early tour. Dave was on the way to the Devil’s Triangle and we had to get home. These partings pain me, since I can only take so much time for motorcycle trips and I don’t know when I’ll see people again. We made it to Buffalo Trade and had a great tour.

I couldn’t help but think (maybe I planned it this way?) that this was a fitting end to the trip, but also a sharp contrast to last year where Four Roses was my consolation prize for missing the Moonshiner 28.

We got absolutely shit on by weather on the way home, but luckily we had saved Lefty’s rain gear from the lost saddlebag. There’s not much else to say. I came home, I hugged my family, and I sat down peaceful and content.

With that, “Moonshiner 28” moves from the “Some day” to “Been there” column on the Rides page. What’s my next adventure? Stay tuned…



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