I’m not one to get overly sentimental over vehicles—in the past nine years, I’ve owned something like 10 cars and six motorcycles. Here’s a look back at the bikes, that can also be read as a guide to gradually upgrading from a beginner’s bike to something you’ll actually want to ride forever (or at least until the next good deal comes around).
1. 1988 Yamaha Route 66 (250cc)
I picked up this little gem for $300 at a tow yard before I even got my motorcycle endorsement. It needed constant carb work, and I ended up selling it for $500 a few years later, in non-running condition. But this is the bike I learned to ride on, so it will always have a special place in my heart. It was so light that when I moved from Oceanside to San Diego many years ago and didn’t have a ramp, my friend literally picked it up of the ground and lifted it into the back of his truck, like it was a bicycle.
2. 1984 Honda Shadow (700cc)
I bought my second bike off some sketchy Craigslist dude in Ramona, about 40 miles northeast of San Diego. When I went to look at this bike, I’d never actually ridden a motorcycle on the freeway. The road from Ramona to San Diego is all twisty mountain roads and freeway. Of course I ended up buying it, and the ride home was a whole new level of exhilarating. This little bike was a trusty companion that never had any issues. Really, the only issue was that it wasn’t a Harley.
3. 1998 Harley-Davidson Sportster Sport (1200cc)
This was my first ever Harley, and I had a serious love-hate relationship with it for the relatively short amount of time I owned it. There were so many things wrong with this bike. One time I removed one of the rocker boxes and found a loose socket just rolling around in there. I also had a love-hate relationship with that paint job. And it ran like crap. But at least I got a proper introduction to the many headaches of being a Harley owner.
4. 2011 Harley-Davidson Nightster (1200cc)
One of the happiest days of my life was when I finally traded in my shitty 1200S for this beautiful (and almost brand new) Nightster. It went through quite a few transformations during the two years I had it, most notably after I got hit by a car and ended up using the insurance money I got from the crash to rebuild it. I put over 20,000 miles on this bike before upgrading to a Dyna, and it’s the only one of my bikes I’ve actually been sad to say goodbye to.
5. 1976 Harley-Davidson Ironhead (1000cc)
Who doesn’t want a completely unreliable second bike taking up space in the garage? I bought a running Ironhead in a swingarm frame in 2014 to use for a chopper build. Today, three years later, it’s still a project. It starts and runs great, but doesn’t shift or stop very well. It could also use some paint. I’m thinking of selling it.
6. 2015 Harley-Davidson Dyna Street Bob (1687cc)
This bike is my daily driver and the love of my life. I was perfectly content riding a Sportster forever, but then I went to the Dream Roll in 2015 and ended up borrowing a friend’s FXDX. Coming home after riding that around all weekend, my Sportster suddenly felt very underwhelming. Maybe two weeks later, I went to the local Harley dealership just to see what my options were. I ended up riding home four hours later on a brand new Street Bob. Stay tuned for a post on all the mods I’ve made to it since.
If there’s a takeaway from this post, I think it’s that you should never feel like you’re stuck with a motorcycle you’re not absolutely in love with. If you buy a bike you like and later realize it’s not the best fit for you, sell that shit! Get something different! As much as I’d like to think that the Dyna is my forever bike, who knows what will happen in a few years? Don’t be too surprised if you see me rolling around on one of the new Road Glides next.