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Regret the Third: Selling Every Softail Heritage I’ve Ever Owned
Gringo was the second Softail Heritage I’ve owned, the third time I bought one. That’s because I bought Pretty Boy Floyd twice.
The first time I bought Floyd, it was brand new. The second time, five years later, it had about 12,000 miles on it. I would go on to own four different versions of the Heritage.
This is how that happens.
One day, I buy a Softail Heritage, the most beautiful bike Harley makes. Although it does not lean much, I love the bike. It is the perfect motorcycle. It glides. It’s balanced. It’s a work of art. I am a happy motorcyclist. I ride it everywhere. Nice and slow. I pose it for pictures. Because riding is about the moment, about the sights, about the scenery and the people, not about making the asphalt wiz past you as fast as possible.
One day, in my rear view mirror I see a Ducati gaining on me. Rapidly.
By the time I get home, the Heritage Softail is too slow, can’t lean to save its ass, uses ancient technology, makes me look like an old man, and is probably about to break down. What was I thinking when I bought it?
So I sell the slow-ass Harley and buy myself a Ducati. This is my 2005 999S:
Few motorcycles are as visually intoxicating as a Ducati.
Above is the 2019 Monster 1200R that I owned a few years later. Over the years I would go on to own an embarrassing number of Ducatis.
You see, when I turn the key on a desmo 4-valve engine with the 41 degrees of overlap, that heavenly engine explodes, pounds, burbles, and gurgles in a symphony that’s part Ode to Joy, part Stairway to Heaven.
When I throw a leg over the saddle and ride it, I transcend this earthly plane.
Soon I’m looking into track days, fitting myself for track leathers, painting half my face red, and learning Italian. Milano, eccomi!
Yes, the riding position is tiring, but I resolve to do more push-ups. Yes, my teeth hurt after a long ride, but I resolve to do more sit-ups. When I wind up riding for 7 hours because I took a wrong turn somewhere near Breckenridge, I lie down on the garage floor and beg God to forgive my sins.
A few weeks later, while I’m rubbing my back at a stoplight, a guy on a BMW GS looking like his mother dressed him pulls up beside me. He nods at me kindly. I ignore him, lean down, grab the bars, and blip the throttle. When the light changes, I drop him. He hasn’t even shifted into first gear by the time I’m dragging my knee across the asphalt at the next curve.
I cackle inside my helmet.
An hour later, I’m lying across a barrel at the local filling station, a little old lady beating my back with a cane because I paid her $20.
Between moans I hear the mumble of a boxer engine approach. The Momma’s boy parks, jumps off the bike, gives me a cheerful greeting, and walks inside. When he returns, he hands me an ice cold water bottle.
Turns out he’s ridden 600 miles already, wants to get in another 300 by nightfall so he can complete his Iron Man 1500 Bun Burner. It’s a warmup for his trip to the Arctic Circle later this summer. He asks me if I know of a gym nearby where he can hit the weights before continuing.
Next day, I’m trading in my miserable, impractical, poser Ducati for a brand new BMW R1250 GS.
The GS can stay with the Ducati or any other sportbike under most street riding conditions. Electronic this. Lean-sensitive that. Active cruise control. Soon I’m strafing asphalt with my left hand on the bar, my right hand around a stogie, the GS electronically maintaining a safe distance from the bike in front of me. I might even google “Multitasking on a motorcycle” for suggestions.
A couple of months later, I don’t understand why I’m just not that into riding anymore. I’ve strafed all the good spots within a day’s ride. I’ve taken long multi-day rides in total comfort. I’ve explored some local dirt roads. It was a lot of fun the first time. Not too bad the second time. But I’m just not that into riding anymore. Something is missing.
And then, because there is a God, I see glinting in the sunlight the most perfect motorcycle ever made …
A week later I got rid of that boring-ass BMW, bought myself another Softail Heritage, and I feel ALIVE again. ALIVE!
I hum me some Lynyrd Skynyrd as I polish that chrome, wax the paint, and lovingly clean each and every spoke on those wire wheels. Life is good again. I’ve been given a second chance. I have no idea what the heck got into me, and I swear, with the conviction that only a returning Harlista can understand, that now that I’m home again, I will never, ever, under any circumstance, let that happen again. Ever. No matter what.
And then …
Regret the First: Selling My ’02 Softail Deuce
The ’02 Softail Deuce was not my first motorcycle, but it was the first motorcycle I fell in love with.
I was living in Massachusetts at the time, a place that specializes in slow emasculation. That’s what the “mas” in the state name refers to. Live there long enough and you’ll understand.
To deal, I had to get out of town on what my riding buddy The Donster called “rage rides.”
They lasted about a week. I rode to Georgia. I rode to Wisconsin. I rode to Maine. I rode to West Virginia. Didn’t matter where. What mattered was getting out of Massachusetts. No better bike for a rage ride than the 5-speed 88″ Deuce. A 95″ motor would work, too, so long as it had a 5-speed.
And no windshield, please. Windshields on cruisers are fascist.
See, at 80 mph and up, a 5-speed kept you in the meat of the powerband. And the pipes loud. With my teeth clenched, my neck hardened against the wind, and my hands in a death grip on the bars, whatever was ailing me disappeared in the vibe of the motor, the roar of the pipes, and the blast of the wind.
I loved my rage rides.
I loved them even more when I started meeting up with other Deuce riders across the country for no damn reason except to check out each other’s rides and laugh. Damn, we laughed a lot. It was a time when laughter was valued more than sensitivity. People have forgotten how to laugh at themselves. And each other.
When I got home from my rides, I got to spend lots of time in the garage cleaning and caring for my Deuce, preparing it for the next ride.
What a treat that was.
Lo and behold, Covetousness crept into my little slice of heaven. The riding season in The State of Eunuch was short, and even shorter in the good riding country of Vermont and New Hampshire.
I was already using thick wind-proof fleece jacket and pants from Aerostich, plus gloves big as sleeping bags. It was not enough. So I bought a windshield to protect me against the New England November cold. That introduced me to the torture of buffeting. I tried to man up and deal, but I could not keep my eyeballs from rattling in their sockets no matter how long or hard I grit my teeth, so I bought fork-mounted wind deflectors.
The combination worked well, but it was, as someone in eMasculateachusetts would say, aesthetically inappropriate. Translation: fugly.
Now, you may not respect a Harley’s agility, comfort, or performance, but you must respect its beauty. That is non-negotiable. If you disagree, die.
Under the influence of Queen Covet, I set about looking for a bike that I could ride longer in colder weather. I ignored my instincts, told my gut to shut up, and forced myself to sell the Deuce so I could buy an ’04 Road Glide.
The Road Glide is a better bike. No doubt about it. It let me ride in colder weather and in more comfort. Unfortunately, it didn’t satisfy. I kept it about a year.
Many years later I bought another Deuce, just to relive the joy of the original, but I had changed. Motorcycling had changed.
Though I enjoyed riding it back to Colorado, Deuce 2.0 failed to satisfy. I wanted more than just a sweet engine. I wanted lean. I wanted a bike that could dance.
It’s true what they say: you can’t go home again.
God Bless Guffey
Guffey is one of those rare places where strange and wonderful things happen that you can’t quite explain but you know they happened because part of you keeps vibrating long after, like an aluminum bat that you whack against a light pole. And if you’re not convinced, stare for a while at the rocks around Guffey. Stare at those rocks long enough and you will start to believe that after the sun goes down druids come out from their secret entrances, gather in the open spaces, and howl like wolves during the full moon.
Guffey is in the middle of nowhere, a plus for motorcycle rides because it takes a while to leave the city behind. And, to appreciate the kind and friendly people of Guffey, you need to make sure the city is way the hell behind you.
Sadly, the Bull Moose has closed. On sunny Sunday afternoons Missus Fender Bunny and I danced among the locals on the big back deck. But the Coronas at Freshwater remains open, and the Guffey Garage always has a treasure or two lying around.
It was remarkably warm for March 7, but the high country was still in the 40’s when the usual suspects, Po Po Rada, Jace the Affable, Bad Ray and Andrea the Pillion, plus Steampunk Risk and BananaShana, led Missus Fender Bunny and me through the canyons and up into the mountains.
Missus Fender Bunny and I ride slow nowadays, so we were able to appreciate the iced-over river beside the road, and how a narrow stream of water slithered over the ice for a spell before sinking back under. We stopped at Deckers.
One of the joys of stopping at Deckers, besides how warm the sun is, is listening to all the bikes ride past and hoping the cool ones pull in to the parking lot so you can talk to the owner. The first bike I noticed ride past was a KTM. Exactly which one, I dunno, but it sounded good, like most KTMs.
Then my heart stopped. Something else was behind the KTM. I couldn’t quite make it out in the sun, but if Phil Collins possessed a moto the way demons are ‘sposed to possess people, the bike Mister Collins possessed would sound like that. I was spellbound. As it passed I realized it was Moto Guzzi’s new V85TT.
Wow. That soulful pounding stayed with me until the Guzzi disappeared behind the next curve. I glanced at my trusty but tame ’11 GSA that cooked my meals and washed my laundry without complaint and knew I had sinned in my heart the way happily married men sin in their hearts when Scarlet Johansen makes them think they make her laugh.
“If you have already sinned in your heart, why don’t you just go ahead and sin in your pocket book?”
That was the Devil on my left shoulder. Yeah. No. But don’t let me stop you. If you want to sin in your pocket book, you can read all about Moto Guzzi’s TT on Motorcyclist.
After warming up in Deckers we rode on to Woodland Park. While we were gassing up in Woodland Park our motley crew decided that, instead of continuing on to Guffey, they would hit the Neiman Marcus sale on men’s rompers before all the cute colors were gone.
They scrambled onto their bikes and hurried back to the city. Missus Fender Bunny and I pressed on toward Guffey.
The road to Guffey is best taken slow. A measured pace reveals cows eating hay on the pastures painted gold by the afternoon sun. Horses with their muscular necks stretched all the way down to reach the hay their owner had dumped on the warm side of the barn. And llamas looking around in their pens, wondering why nobody speaks Spanish around these parts.
Como? Que cosa?
The cows, the horses, the llamas, and the pretty hills all around have a way of restoring your soul to its God-given groove.
If you don’t decide to stop right THEN, and not any later, as you crest the ridge above the town of Guffey, you miss the glorious view of the Sangre de Cristos, one of the most majestic mountain ranges in America. We managed to pull over, even though there wasn’t much of a shoulder.
Next time I’m taking my good camera, dangit. If you squint at this picture you can see the Sangres. Wish I could have pulled them in with a good telephoto lens.
Once in town we skirted the Guffey Garage and took a Right. Then we took a Left on Cañon street, rode past the Post Office and the Rolling Thunder Grill and took another Left on 8th street. We stopped at The Corona’s at Freshwater, which is where the fun began.
While Laura went inside to freshen up, I walked toward the bikes and trikes parked across the street. As I was inspecting the heavy metal, a really big guy in a watch cap approached me and asked me what I was up to.
I can’t stop staring at Harleys.
He smiled. What are you riding? I pointed to our bikes parked around the corner all by their lonesome.
Oh hell no.
That just won’t do, he said. Then he put his big arm around my shoulder and invited me to follow him inside.
The Freshwater is a rustic place with a welcoming feel. Not too many of those around, any more. Some of the newer places try to imitate the real thing, but they can’t pull it off because they don’t have the right people inside.
About a dozen veterans had ridden over from Colorado Springs and taken over the joint. By the time I walked in Missus Fender Bunny had announced to the room that she needed a hug and the vets were lined up, giving her hugs one after the other, some getting in line twice, the waitress patiently winding around the embraces to deliver burgers and fries.
You know how with some people you don’t even need to be introduced, you’ve just known them all your life? That’s how it was with the veterans and their wives. In a matter of minutes they were informing me that I could sit in the backwards chair as my service in the Chair Force only counted for 2/3, and I was splainin’ them that somebody needed to be smart enough to save their grunt asses from the Taliban. Or, for some of them, the Viet Cong.
I’m not really sure whether we actually did stand on the tables and sing verses of our respective service songs at each other or whether I just imagined it, we’re talking about Guffey after all, but before we knew it, we were swapping stories about life in the service like old friends and the grill had become twice as big as it had been when we first walked inside.
It was decided that Missus Fender Bunny and I were riding with them to Cañon City and the Springs, and that was that. Before we left, each of us took turns stapling a dollar bill to the ceiling. Accustomed to this mountain tradition, we obliged.
Kindly forgive the neck torque, but I need to make a note about Evos. I’ve owned two Evo Softails. The Evo is favorite sounding Harley motor. Something about the Evo’s lope is lovely and it tops even the Twin Cam’s lope. But the two I owned and every other Evo I have test ridden or sat on vibrated terribly. In 30 minutes my hands would invariably go numb.
I noticed that the 99 Heritage a veteran named George was riding had steel grips. Most Evo Softails, because they’re solid-mounted to the frame (instead of rubber-mounted), have rubber or leather grips with tons of foam or other material to dampen the vibration. George’s Evo had steel grips.
Either you are the world’s toughest biker, or you have one smooth Evo.
I said to George. Instead of responding, he sat on his bike, pulled out the choke, and fired it up. At idle it vibrated plenty, of course. That’s part of the charm. But I rolled on the throttle and at what between 2,000 and 3,000 RPM, that steel grip was as smooth as the chrome on my Street Glide. Unbelievable. I’ve got to build me one, I decided. An EVO-powered Softail Custom.
Or maybe another Fat Boy.
Damn if he doesn’t look like my pal Darrin, from Cotopaxi!
Anyway, we rode with the vets into Cañon City along route 9. These guys were good riders. A mixed flock of Harleys, Gold Wings, Indians, trikes, and what not. Plus Missus Fender Bunny on her Honda and me on the betrayed GSA. I’m not a fan of riding in formation, but these guys knew how to do it right. And do it well. We kept a good pace and, when traffic separated us, they got everyone back together as smoothly as an experienced wrangler gets strays back in line on a cattle drive.
Which reminds me, if you haven’t seen Lonesome Dove, see it.
We hung out a bit in Cañon City, exchanged warm good-byes, and mounted up and headed toward the Springs through some back roads that were new to me. In the Springs we split off and went our own way, Missus Fender Bunny and me full of good feelings for the veterans and, once again, without fail, for Guffey.
Old Man Ramsey 
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