Harleys and Whiskey Part 1: Riding a Harley Fat Bob around Kentucky’s Beautiful Bourbon Trail


The ride never seems long in Kentucky on the back of a Harley. No matter how far you go the rolling green hills and white picket fences just chase the road along side of you and there is enough variety in the landscape to never get bored.  The trees grow over the tops of the road giving periodic shade at just the right moments. The open blue skies provide plenty of vitamin D to keep your skin warm.  This friend is my Wednesday at the office, one of the best Wednesdays of my life.

When some of the guys from Harley Davidson approached me about taking one of their bikes out for a ride there was no hesitation, the only deliberation was what would be the perfect Harley Davidson motorcycle and the perfect ride? It wasn’t long before I stumbled across the idea of riding around the Kentucky Bourbon Trail.  It seemed only natural to want to ride a Harley rocket ship around the back roads of arguably one of the greenest and most beautiful states in the US that just happens to house all the Bourbon distilleries in the country.

My adventure on a Harley started out at Man O’ War Harley Davidson in Lexington, Kentucky.  I have a rule on this blog, I don’t write about any business establishments unless the service I was provided was other world-ly and beyond expectation, good service isn’t good enough for a mention since it is expected.  Well, that was exactly the case at Man O’ War, the experience was exceptional.  In my life I have never encountered a level of professionalism and just simply stand up people at any business, motorcycle or not, like I did here.  Particularly I want to name drop Josh Bentley.  This guy was not only a class southern gentleman, but also just a good guy you’d want to get a beer with. He made the process of renting a bike as painless and enjoyable as humanly possible.  It was serendipitous to have found such a great place on H-Drentals.com to really ride my first Harley.  There are a million great compliments I could hand out to Man O’ War and Josh, but I’ll simply say this and leave it, when I do buy a Harley Davidson I will drive the 2 hours to get it from Man O’ War instead of the 15 minutes to the dealer down the street from me because the quality of service was that impeccable.  Cheers Man O’ War HD.

Josh saw to it that I got the Harley that fit my needs and style of riding. I wanted a mean looking bastard that could handle well in the corners and take off like missile.  I’m a sucker for a bike that has great handling because my style of riding is technical and I like to get a low lean in a turn and really feel the dips in the road.  Josh didn’t let me down and got me setup with a 2013 Dyna Fat Bob . This double head lighted beast had a chunky frame, but somehow road and handled like a much smaller more agile bike.  It was a perfect fit.  So, on the Fat Bob I headed out of Lexington and made my way on the Bourbon Trail.

2013 Harley Fat Bob
2013 Harley Fat Bob

The Kentucky Bourbon Trail is the route around the state of Kentucky that takes you on a tour of America’s bourbon whiskey distilleries where they make and store the finest bourbon whiskies in the world, which just so happens to be my other passion aside from motorcycles.  Coincidentally, multi-million dollar racehorse farms owned by sheiks and some of the most powerful men in the world surround the roads in between these distilleries making the ride as impressive as it is beautiful.

On the way to my first distillery, Woodford Reserve, I eased into the bike and learned how it reacted to the road and felt in turns.  The breaking in process was short, because even though this 103 cubic inch engine rumbled the rubber mounting provided one of the smoothest rides I’ve had the pleasure to be on.  I’m here to tell you that roaring through endless horse fields on a Harley is an experience anyone that calls himself a man should have at least once in their life.  I took a road named Old Frankfort out of Lexington and highly recommend you do the same. Once out of the city limits Old Frankfort becomes a hilly straight away through the countryside that makes it tough to want to see the distilleries and get off the bike.

Woodford Reserve Distillery
Woodford Reserve Distillery

Two distilleries, Wild Turkey and Four Roses, and a few hundred miles later I was loving the Fat Bob in the turns.  Kentucky has some great switch back turns that weave you around its many hills.  Up, down, left and right the Fat Bob was always up to the challenge and took every corner with ease. Josh was right, this bike could handle.

The Fat Bob has considerably more power than my day-to-day Kawasaki, so I had one last test for it. On the way back to my hotel in Lexington I wanted to see what 103 cubic inches could do on a highway straight away. Well, I’m here to tell you what I saw was the blurry markings on the road because this bike can haul ass and get up and go in hurry. When you are holding on to the drag style bars and the wind is screaming and the front tire is devouring pavement the only reaction you can have is a big dumb ass smile on your face from ear to ear, at least that’s how it went down for me.

Usually I’ll say something is Shameless approved after I try it, in this case the list is too long and the experiences are too great. Sometimes life is so good you stop assessing and you start enjoying.  Of course the Fat Bob, Man O’ War HD, and the many perfect ever changing roads of Kentucky are Shameless approved, but this is one of those times I encourage you to find out for yourself. 

The Wild Turkey Distillery
The Wild Turkey Distillery

For more information about the bourbon whiskey distilleries I visited on the Kentucky Bourbon Trail come back and check out tomorrow’s article, “Harleys and Whiskey Part 2: The Kentucky Bourbon Trail and the Master Distillers’ Master Distiller, Jimmy Russell. “


If you are in the United States and looking to rent a Harley for the Kentucky Bourbon Trail I recommend Man O’ War Harley Davidson located at 2073 Bryant Road in Lexington, Kentucky (phone number: 859-253-2461), ask for Josh Bentley or Tim Curry (also a very helpful guy).  Or to find a Harley Davidson rental provider near you check out the easy to use H-Drentals.com (I used this to find Man O’ War HD).  You will need a valid motorcycle endorsement on you drivers license to rent a Harley, but they will provide you with a helmet, rain gear, a bike lock, and even a map at no extra cost, which is pretty sweet.

Until next time, may your journey be long, your gas tanks remain full, and all your riding be shameless.

**On this ride I visited Three Whiskey distilleries over six hours and consumed exactly three shots of liquor and a massive lunch over that period of time leaving me 2 hours in between each shot to safely digest and drive my motorcycle. I do not condone nor encourage drinking alcohol and driving. Harley Davidson, the Kentucky Bourbon Trail, and myself all stand against drunk driving. Please remember to be responsible and if necessary call a taxi if you drink too much. Motorcycles do not mix with intoxication. To have shameless travels you have to be alive, to be alive you have to use your head. Safe riding and driving are 100% definitely Shameless Approved. Godspeed riders.

Keep on Riding
Keep on Riding


Next entry: Harleys and Whiskey Part 2: The Kentucky Bourbon Trail and Master Distiller Jimmy Russell

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