2009 Heritage Classic

2009 Harley Davidson Heritage Classic

Project: Scarlett

The Story Behind the Build

This is one of those stories that isn’t really about customizing a bike—it’s more of a rescue mission to bring one back into service.

Back in 2020, we decided to move from Colorado Springs to Northwest Arkansas. When the time came and I sold our house in Colorado, I hadn’t yet secured a new one in Arkansas. The place we were temporarily staying only had room to store two Harleys—and I had three. So something had to go.

Now, the 1987 isn’t going anywhere. There’s a whole write-up on that bike and why it’ll never leave my stable—it’s just got too much personal history. So that one was non-negotiable. That left me with a choice between Luella’s 2015 Fat Boy (which I’ve also written about) and my 2018 Breakout.

Surprisingly, the decision was easier than you might think. Even with all the work and money I put into the Breakout—and yes, I’ll do a separate piece on that build—it just never won me over. “Hate” is a strong word, but let’s just say I never really fell in love with it. It always felt more like a piece of transportation than a motorcycle I was emotionally connected to. I didn’t shed a single tear when that one left the garage.

So fast-forward: I’m living in Arkansas and riding the ’87 as my daily. Now, if you’ve ever ridden older Harley technology, you know the creature comforts of newer models become very obvious real fast. Even though the ’87 was fully restored and for all intents and purposes was brand new, it was still 1980s tech. And after 50 to 100 miles, I was ready to get off. The riding position is rough, even with extended forward controls, and it just isn’t ideal for longer rides. I don’t know how those guys in the 70s did high mileage rides on those old shovels.

At the time, I wasn’t quite sure what my next main bike would be so I wasn’t prepared to invest heavily into the unknown. I was still toying with the idea of a Street Glide—thankfully, I never pulled the trigger during this time, because something else popped up later on down the road (more on that in another write-up).

As usual, I was doing my Craigslist rounds, scrolling through listings out of habit. I came across one with some of the worst photos I’ve ever seen. Like, they looked like they were taken with a flip phone from 2005—blurry, dark, you name it. I opened the ad just based on that as I found it hilarious. But one picture caught my attention: the odometer. It read just over 2,300 miles. Higher mileage doesn’t scare me if the owner has maintenance records. If they don’t and you buy something with higher mileage then you may be walking into a landmine field. With that said low mileage bikes are always worth looking at as the owner hasn’t ridden it enough to make bad decisions. The listing was for a 2009 Heritage Classic, and I thought, “Hmm… that’s the Twin Cam 96—not bad. Cooler than the 103 and known to be a pretty solid engine.”

Now, I’ve never really gravitated toward the Heritage. It’s Harley’s version of a softail bagger—a great bike, but it never quite fit my style. Still, the price wasn’t bad, so I gave the guy a call and went to check it out.

He opened the garage, and there it was—really solid condition. Just one small scratch on the side of the tank, nothing serious. I asked him for the backstory, and he told me it was originally his best friend’s dad’s bike. The dad had bought it new, rode it a couple thousand miles, and then stored it up on a lift in his garage. Every time my seller visited, he’d ask the dad if he’d sell it, and the answer was always no—until one day, out of the blue, the dad said, “You still want that Harley?” And just like that, he bought it.

The young man rode it a bit—maybe 300 miles—and then life happened. He found out his wife was pregnant, needed money, and she didn’t want him riding anyway. So the bike went up for sale.

I think he listed it for about $8,000, which wasn’t a huge stretch. I didn’t try to lowball him. He was a young guy starting a family, and the bike was in great shape—it just needed the usual rehab after sitting for so long.

So I brought it home and rolled it into the shop. Of course, it needed all the basics: fresh fluids, tires, torque checks and a deep cleaning. I filmed a video on cleaning out the tank, which is one of the bigger jobs—between stuck fuel-level floats and gunk buildup from old gas, it was pretty nasty in there. Trust me, when you watch the video, you’ll see what I mean.

The tires were the original whitewalls, and although the rubber had tread the sidewalls were completely shot. Safety issue, no question—so onto the tire machine they went. I didn’t do any heavy customization since I wasn’t planning to keep it long. Just the basics: heated grips, comfort tweaks, safety checks. Oh, and if you’ve ever added heated grips on a Heritage with those buckhorn handlebars—you know it’s not fun. The saddlebags were also the standard sagging collapsed look you see on those old Heritage models. I did the Papa Bags inserts and got them standing upright like a soldier.

Once I got everything buttoned up with fresh fluids and fixes, I really clicked with that bike. It rode beautifully—smooth, planted, comfortable. I didn’t expect to get so attached to it, but I did. It felt like riding down the highway in a Barcalounger.

Still, like I mentioned in the Slim write-up, we had too many bikes and something had to go. I listed both the Fat Boy and the Heritage. To my surprise, the Heritage sold first.

Here’s the kicker: I rode that Heritage about 10,000 miles over a couple of years, then turned around and sold it for $8,500. That’s $500 more than I paid—so I got two years of riding and the profit paid a good percentage of the parts I put in it at purchase. Not bad at all.

Funny thing is, I didn’t think I’d ever bond with a Heritage. But looking back, I really enjoyed that bike more than I expected. It was one of the comfiest rides I’ve ever had. Some fellas talk about feeling like they lost a child when they sold a bike they loved. For me it was an old comfortable pair of slippers that I still miss sometimes.

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