The Story of My Harley Davidson Night Train

Normally, a feature vehicle article is all about the details of the vehicle itself. In this case although I love my Harley Davidson Night Train, I really don’t think it’s that interesting. It’s mostly stock after all. What is interesting however, is the story of how it came to be my bike. I’ve decided to share that instead. I hope you enjoy.


The Story

Back in 2014, I decided to purchase my first motorcycle. At the time, the insurance companies in Ontario were really cracking down on sport bikes. By cracking down, I mean raising premiums through the roof (some people received 80% increases for no reason!).

Although I love sport bikes and I’ve always wanted one, I knew that a bike of that nature would land myself in trouble. The insurance situation was the final nail in the coffin for that idea. I’d still love to add one to my fleet someday though.


So, Why a Harley Davidson Night Train?

Most people will buy a small 250cc learner bike when they start riding. The reason being that they’re small and easier to maneuver. They quickly grow out of them and end up selling them a year or two later to buy the bike they originally wanted in the first place.

I chose to skip that step altogether. At 6’3″, 230 lbs and with a lifetime of mountain bike experience under my belt, I felt that I could fast forward straight to the bike I wanted: A Harley Davidson Night Train.

Why on earth would someone in their twenties want a Harley? Well, I can tell you it wasn’t because of the TV show Sons of Anarchy. It was actually because my dad has owned one for many years.

A Dyna Wide Glide, to be exact. After being around it for countless hours, working on it, sitting on it, and rolling it around the garage, I already knew that bike fit me like a glove. This made the Wide Glide the starting point for my motorcycle hunt.

I wanted something a bit different though. My dad’s bike is absolutely gorgeous. Beautiful pearl white paint, dripping in chrome, and spotless nearly all the time. His bike turns heads everywhere it goes. It even won the show and shine at the first ever Bike Rally in Wasaga Beach. But despite my loud, shiny red sports car, I really don’t want flashy vehicles.

As a matter of fact, I like to fly under the radar if possible. An industrial, mostly blacked out look was exactly what I was after. I spent a few hours searching online and found out that the main difference between the Wide Glide and Softail was the rear suspension design.

Other than that, the bikes had very similar dimensions overall. At that point, I realized that the Softail Night Train was the bike for me. Similar sizing to the Wide Glide, but with the dark and subtle looks that I desired.


The Hunt

It didn’t take me long to figure out that although the Night Train isn’t necessarily a low production model, they also aren’t very common.

The ones that I could find were a lot more money than I wanted to spend. So I began looking at Wide Glides and regular Softails, but none of them really made me excited. Then I started looking at American bikes on Ebay…

Not only were there quite a few Night Trains listed, but they were cheaper. I found a no-reserve auction for a bike in Missouri that no one was bidding on. It seemed too good to be true at first.

I examined the photos closely and it appeared to be in good shape. The title was clean. I even messaged the seller to find out if he was actually willing to release the bike for his starting price, and he was!

I put myself through a quick crash course on what was involved in buying a bike from the states and started crunching numbers. At the price it was going to cost me, it still seemed too good to be true. In classic “You Only Live Once” fashion, I decided to place a bid anyways with about 30 minutes left to go.

I figured if no one outbid me, it was meant to be and I’d figure out how to get it home. If someone did outbid me, I’d give up and head back to reality. 20 minutes to go, and I was still the only bidder. 15 minutes to go. 10 minutes to go. Was this actually happening? 5 minutes to go.

“You have been outbid on this auction.”

That sucker punch felt like it landed square on my jaw. I’d told myself if anyone else bids, the bike would be theirs. But like Mike Tyson famously said, “Everyone has a plan until they get punched in the mouth.” Apparently my game plan all along, regardless of whether I knew it or not, was to own this bike at all costs.

I decided to limit my emotional attachment and after reasoning with the two good vs. evil characters floating over my shoulders I chose to bid one last time with only 3 minutes remaining. I raised the bid of my now faceless enemy by $200 and waited.

This was the most I was willing to pay and I knew it was truly a do or die moment. I wasn’t going to keep going back and forth after this bid. This was it. Those final 3 minutes felt like an eternity. Finally, a new message. “You have won this auction!

Oh crap. I guess I’m going on a road trip to Missouri.

I went through all of the requirements to import the bike to Canada, reserved a trailer rental, loaded up my trusty (or so I thought) Jeep Grand Cherokee and we were off to Sedalia, Missouri.



The Adventure

Almost immediately after crossing the border into Michigan, I noticed the Jeep not only had a growing exhaust leak, but it wouldn’t stop hunting for gears. This would make sense if I was towing a heavy load, but an empty motorcycle trailer couldn’t weigh more than 1500 lbs tops.

I knew my Jeep was properly maintained and never abused, but I couldn’t shake the thought of Chrysler transmissions and their reputation for failing.

After a few more hours of driving I figured out that if I held my foot at an exact spot in the throttle, the transmission would at least try to stay in one gear.

We decided to press on in hopes that we wouldn’t end up stranded in the middle of nowhere, in a puddle of ATF. After all, I had a deadline to be at the border with the bike by Sunday morning.

The Hills Have Eyes

As if the mechanical worries weren’t enough, we ended up going through a detour that took us so far out of our way that we no longer knew what state we were in anymore.

It was late at night and we were driving through hills that looked like something from a horror movie. The Jeep was still acting up and we knew that a break down was possible at any moment.

Finally, we rolled into our hotel. Exhausted from an 11 hour drive that quickly turned into 19 hours, it was time to rest up before meeting with the seller of the bike in the morning. I don’t think I’ve ever been so happy to see a bed in a hotel room before. I was both surprised and impressed that the Jeep had held together this long too.


Small Town America

The next morning I went to the seller’s house and picked up the bike. It was in a tight little neighborhood just down the street. According to the seller, his grandparents built a group of these houses half a century ago, and his whole family lives together in this compound.

I love small town America. This felt like the most authentic setting to purchase a Harley Davidson. The bike was in even better shape than I expected, and the seller was a pleasure to deal with. Despite the rain getting stronger and stronger, I left with the title in my hand and the bike on my trailer.

I had read online that there was a new rule for importing motorcycles into Canada that required them to have the stock exhaust installed before inspection. My bike had aftermarket pipes on it, so I was planning on tracking down a stock set locally when I got home.

What we didn’t realize when we rolled into town in the middle of the night, was that there happened to be a Harley Davidson dealership literally across the street from the hotel! We decided to check it out, and sure enough I was able to scoop up a brand new stock exhaust for only $50.

It was now time to head home to Canada and the rain had really picked up by this point. Despite seeing the violent riots in Ferguson Missouri all over the news, we decided to risk heading that direction through St. Louis to avoid the massive detour we got stuck with the night before. This turned out to be the right decision and we sailed right through.

The rain became increasingly stronger as the sound of the Jeep’s engine revving up and down became increasingly more annoying. By the time we got to the prairie section of Illinois just south of Chicago, it had escalated to the worst rain I think I’ve ever driven in.

The trip had now turned epic and it was hard to tell what our biggest threat was – the bad weather or the health of the Jeep.

Regardless, we pressed on towards the border.

Thanks to the storm and having to stop periodically to stretch and let the Jeep cool off, the drive home ended up being much more than 11 hours as well.

We drove straight through the night and finally landed at the Canadian border around 5am. Now keep in mind, at this point I was exhausted from driving non-stop and perhaps I wasn’t in the most clear-thinking state of mind.

Well, that was stupid.

I knew how important it was not to miss the export office on the US side (otherwise I wouldn’t be able to bring the bike into Canada) so I was a little paranoid about driving past it. We came up to a bridge and with no other motorists around, I thought I’d pull off to the side of the road and ask the toll booth attendant for directions to the office.

As I walked up to the booth, she turned around and placed her hand over the gun on her hip. After mouthing a few choice expletives, she yelled at me to get back in my vehicle. So I did.

Apparently, I had just snuck up behind an American Border Patrol agent… in the middle of the night. Like I said, not exactly one of my finer moments. Happy to not have any fresh new holes in my body, I pulled up to her window. She guided me to the export office I so desperately needed to find and sent me on my way.

She was still not happy with me, but that was understandable due to the less than stellar first impression I provided. From that point on, it was just a matter of doing the paperwork on both sides of the border. Man, did the Canadian agents seem friendly and relaxed in comparison!



Back in Canada

It was great to be back on home soil. 4 hours later, I was unloading my new Harley onto my driveway. The Jeep survived. The storm didn’t kill us. And I didn’t get shot, tased, or detained by a border patrol agent.

All in all, the trip was a success. By the way – I later realized that the entire problem with the Jeep wasn’t transmission related at all. It was simply a faulty Throttle Position Sensor; one that I could have purchased and replaced on the side of the road at any time if I’d known. Live and learn.


One very dirty bike

Thanks to the combination of the gnarly storm, the open trailer, and the spray from the all-terrain tires on the Jeep, the bike was absolutely filthy. The road grime on it appeared to be half an inch thick.

It had a few ugly accessories still installed by the previous owner. This wasn’t exactly the bike of my dreams at this point, but it was mine. I knew that unlike the exporting process, the remaining issues were in my control and I could easily tackle them one by one until the bike was perfect.

The first order of business was to remove any unwanted aftermarket parts. The skeleton mirrors, crash bar, saddle bag mounts, and windshield were all tossed. Next came a thorough cleaning and a quick polish of the paint.

Then the stock exhaust was installed and I brought the bike to Canadian Tire for its RIV inspection. The Vance and Hines pipes were put back on right away, and all that was left was a safety inspection at Kitchener Harley. A front tire, rear brake rotor, and a new battery were installed and she was good to go.



About The Bike:

The bike is mostly stock. It has an Arlen Ness lowering kit in the rear, smoked LED turn signals, K&N filter, Vance and Hines Big Shot exhaust, and a few other small aesthetic upgrades. The carburated Twin Cam 88 motor is completely stock, although I’d like to have it properly dyno tuned in the future.

I’ve made a few changes since then but mostly just minor ones. I replaced the mirrors, and grips, added an oil temperature gauge, and painted the fork lowers black.



Detailing Products Used:

I gave the fuel tank and fenders a multi step paint correction, followed by ceramic coating with Gtechniq Crystal Serum Light topped with Gtechniq EXOv3. This has helped to keep the soft Vivid Black paint from scratching after every wash.

The flat black pieces on the engine are dressed with S100 Engine Brightener. I have yet to find a better product for this purpose. It goes on shiny at first but I buff it down to a nice satin finish. It will typically last me half a season. I’ll usually touch it up when I’m doing a more in depth cleaning before a bike event. I like to use Mother’s Chrome Polish on all of the chrome, and Gtechniq L1 Leather Guard on the seat.



Would I do it again?

Throughout the following years, this bike has been rock solid. As far as maintenance and repairs go, I’ve done nothing more than change the fluids and replace the front brake pads once. The myth that Harley Davidsons are unreliable is completely untrue from my experience.

This 2000 Night Train has taken me all over Southern Ontario without a problem. The Twin Cam equipped bikes of the mid 2000s are well built and a fantastic value if you’re looking for your first Harley. I’m completely happy with mine, and despite the stressful trip to the US to buy it, I’d do it again in a heartbeat.

In the end, I wound up paying less than half of what this bike would have cost here in Canada. It also came with memories that I’ll never forget.

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