Jess Rips Garage: My Life Told Through Motorcycles
Some people remember the different chapters of their lives by the houses they lived in, the jobs they worked, or the places they traveled.
I remember mine by the motorcycles that have been parked in my garage.
This is my personal riding timeline. These motorcycles challenged me, humbled me, carried me through some of the darkest seasons of my life, and somehow always helped me find my way back to myself. Every one of them left tire marks on my story and helped shape the woman you know today as Jess Rips.
This isn’t a list of my favorite motorcycles or the most expensive bikes I’ve owned. It’s a collection of the machines that marked the different chapters of my life. Each one teaching me something I couldn’t have learned any other way.
So, come with me as we take a ride down memory lane.
Welcome to Jess Rips Garage.
🏍️ Bike #1 — 2002 Honda Shadow 750
The Chapter: The Terrified Beginner
What It Taught Me: Courage
I was 18 years old and had never ridden a dirt bike, ATV, or any other two-wheeled machine in my life. Looking back, buying my first motorcycle with absolutely zero riding experience probably wasn’t the smartest decision… but I was completely determined to figure it out.
If you’d like the full story of how I ended up buying my first bike and where that determination came from, be sure to read “The Motorcycle That Changed My Life.” That’s where it all began.
The Honda Shadow became my classroom.
I practiced in the yard. Rode up and down my neighborhood street. Then ventured onto roads that felt way bigger than they actually were. Every ride stretched my comfort zone just a little farther than the last.
I was the first person in my family to ride a motorcycle, and I didn’t have anyone showing me the ropes. Everything felt new. Everything felt intimidating.
Looking back now, I’m incredibly proud of that scared eighteen-year-old version of myself. She didn’t have experience or confidence—she just had determination.
And sometimes, that’s enough to get you started.
Lesson Learned: Confidence didn’t arrive all at once. I built it one shaky mile at a time.
🏍️ Bike #2: 2003 Suzuki Hayabusa 1300
The Chapter: Full Gorilla
What It Taught Me: Respect
After less than a year on my Honda Shadow, I made what was, in hindsight, a completely ridiculous decision.
I bought a Suzuki Hayabusa.
If you’ve been riding for a while, you’re probably shaking your head right now… and honestly, you should be.
Most people would have upgraded to something in the middle. A 750 sport bike, maybe a 1000cc, but not twenty-year-old Jess.
My logic was simple. “If I’m eventually going to want a bigger bike anyway, why spend money buying two?”
Makes perfect sense when you’re twenty… and absolutely no sense when you’re forty-three.
The Hayabusa became my daily transportation through the rest of college.
Rain? I rode.
Heat? I rode.
Need groceries? I figured it out and rode.
It was also during this chapter of my life that I discovered something just as life changing as the motorcycle itself… the riding community.
I started going to local bike nights, meeting riders from every walk of life, and realizing that motorcycles have a funny way of bringing complete strangers together. It didn’t matter what you did for a living, where you came from, or what kind of bike you rode. We all spoke the same language.
Looking back, those nights played a huge role in keeping me passionate about riding.
Now… I’d also like to take a moment to thank God that smartphones and social media weren’t really around back then.
Because let me tell you… I did some incredibly stupid things.
Fast motorcycles and twenty-year-old confidence are a dangerous combination.
I genuinely believed I had this whole riding thing figured out.
Spoiler alert… I didn’t.
Thankfully, I survived those years with nothing worse than a few stories that probably shouldn’t be repeated and a much healthier respect for motorcycles than I started with.
The Hayabusa wasn’t just a faster motorcycle. It was the bike that taught me one of the most valuable lessons of my riding career:
Horsepower doesn’t make you a better rider. It simply gets you to your mistakes a whole lot faster.
Favorite Memory: Rolling into my first local bike nights and realizing I’d found my people.
🏍️ Bike #3: 2009 Honda CBR1000RR
The Chapter: Finding My Way Back
What It Taught Me: Sometimes the Road Waits for You
Life has a funny way of changing your priorities.
After my Hayabusa, I stepped away from riding for a few years. I had my youngest daughter, and being a mom became my entire world. Motorcycles weren’t forgotten, they were simply put on pause while life happened.
Years later, my ex-husband started talking about wanting to learn how to ride.
So naturally… We bought a 2009 Honda CBR1000RR.
It was yellow and black, sleek, aggressive, and everything you’d expect a sport bike to look like.
Ironically, I didn’t put nearly as many miles on this bike as the ones before or after it.
Most of my memories are simple ones, easy rides around town and spending time on two wheels again.
But the memory that stands out the most? Teaching him how to ride.
For a while, I found myself backpacking behind him until he learned the same skills I had once struggled through myself. It was a completely different experience than my first years of riding, and one I’ll always remember.
The CBR only stayed in the garage for about a year, but it deserves its place in this story. Not because of the miles we traveled… But because it marked my return to motorcycling after life had taken me in a different direction.
Sometimes the road doesn’t disappear. It simply waits patiently for you to come back.
Favorite Memory: Backpacking my ex-husband and photographs still circulating of it to this day.
Lesson Learned: Life may pull you away from riding for a season, but the road will always be there when you’re ready to come home.
🏍️ Bike #4: 2020 Harley-Davidson Low Rider S
The Chapter: Slowing Down Isn’t a Bad Thing
What It Taught Me: The Journey Is the Destination
After spending years on sport bikes, I never imagined I’d end up on a Harley-Davidson.
In my mind, Harleys were… different.
Sport bikes were about speed.
Harley riders were those old guys hanging around the dealership or gas station who always had another story to tell. Every conversation somehow turned into a ride they’d taken twenty years ago, a friend they’d met on the road, or a tiny roadside diner that supposedly had the best pie in the state.
I didn’t get it. At least… not yet.
As it turns out, I needed exactly that.
The Low Rider S completely changed the way I looked at motorcycles. Instead of wondering how fast I could get somewhere, I started wondering where I wanted to go.
Weekend rides became less about the destination and more about the roads in between. I found myself taking the long way home. Stopping at little roadside restaurants. Exploring places I would’ve blown right past on a sport bike.
For the first time, riding wasn’t about adrenaline.
It was about peace.
The Harley community welcomed me with open arms, and before long I realized I wasn’t just changing motorcycles…
I was changing as a rider.
Looking back, the Low Rider S wasn’t the fastest bike I’d ever owned. But it may have been the one that changed my life the most.
It planted the seed for something much bigger: cross-country trips, motorcycle travel, and eventually the adventures that would become Rips Unfiltered.
Sometimes the best thing you can do isn’t twist the throttle a little harder.
Sometimes it’s slowing down long enough to appreciate the ride.
Lesson Learned: I didn’t stop loving motorcycles when I left sport bikes behind. I simply discovered there was a whole different side of riding waiting for me.
🏍️ Bike #5 — 2021 Harley-Davidson Road Glide Special (Billiard Red)
The Chapter: The Adventure Begins
What It Taught Me: Home Isn’t Always a Place
Getting on my first Harley-Davidson was intimidating.
I’m an unusually tall woman, but that didn’t make the weight of a touring bike any less intimidating. At the time, I wasn’t even comfortable test riding anything bigger than a Low Rider S.
A Road Glide? No chance.
Or at least… that’s what I thought.
The more I rode, the more I realized my goals were changing. Highway miles were getting longer, and I quickly learned that if I wanted to travel the way I dreamed about, I needed two things: a fairing to cut the wind and enough storage to pack more than a backpack.
Then one day, I walked into Palm Beach Harley-Davidson.
Sitting on the showroom floor was a 2021 Billiard Red Road Glide Special.
I can still picture it. Before I even rode it, I knew.
That was my motorcycle.
I wasn’t looking for a bike that was faster. I was looking for one that could take me farther. This motorcycle opened a door I never knew existed.
Weekend rides slowly turned into weekend trips.
Weekend trips turned into multi-state adventures.
Before long, I found myself planning vacations around roads instead of destinations.
The Road Glide introduced me to motorcycle touring in a way no other bike had before. Longer days in the saddle became normal, and I started realizing just how much of this incredible country could be experienced from behind a set of handlebars.
Then came another lesson. One I wasn’t expecting.
As my confidence grew, so did my ambition.
I started pushing my limits, stunting, convinced I was becoming a much better rider.
The truth?
My confidence had outpaced my skill level.
The full story is one for another blog, but one ride ended with a crash that changed the way I looked at motorcycles forever.
It was bad.
More importantly, it was humbling.
That accident forced me to take an honest look at my own limitations and reminded me just how quickly things can go wrong when confidence gets ahead of ability.
Ironically, that crash also sparked another passion.
When Harley-Davidson handed me a repair estimate for nearly $13,000, I had a decision to make.
Replace everything with stock parts…
Or build something better.
I chose the second option.
That accident became my first real introduction to customizing motorcycles.
If I was already replacing parts, why not upgrade them?
Looking back now, that unexpected setback became the beginning of my obsession with performance baggers. It completely changed the way I looked at building motorcycles, and without realizing it, it set the stage for every custom build that followed.
Some of my favorite memories weren’t at famous landmarks.
They were the unexpected moments in between.
A quiet sunrise at a gas station. A conversation with a stranger who became a friend.
A scenic backroad I never planned to find.
Some of the best meals I’ve ever eaten came from little roadside restaurants I would’ve ridden right past years earlier.
Looking back now, I realize this motorcycle was laying the foundation for everything that came next. It gave me the confidence to travel farther, dream bigger, and ultimately introduced me to the world of custom motorcycles.
It wasn’t just taking me across state lines.
It was quietly changing the direction of my life.
Favorite Memory: Realizing that some of the best days on a motorcycle don’t require a destination, just a full tank of gas and enough daylight to keep exploring.
Lesson Learned: Sometimes life disguises your greatest opportunities as your biggest setbacks. That crash didn’t end a chapter... it started one I never saw coming.
🏍️ Bike #6: 2023 Harley-Davidson Road Glide “Gnarly Glide”
The Chapter: Built, Not Bought
What It Taught Me: Never Be Afraid to Stand Out
By the time I bought my 2023 Road Glide, I had already fallen in love with motorcycle travel.
But this motorcycle was different.
This wasn’t just the next bike.
This was the first motorcycle that truly reflected me.
What started as a stock off the show room floor Road Glide evolved into a full frame off custom build. Every modification had a purpose. Every part was carefully chosen. It wasn’t about trying to build the loudest or most expensive motorcycle, it was about creating something that represented my personality every time I threw a leg over it.
Before long, people weren’t saying…
“Hey, nice Road Glide.” They were saying…
“Hey… that’s Jess’s bike.” That still blows my mind.
This motorcycle carried me through 38 states and two countries in just sixteen months. It became the bike I trusted to disappear for days at a time, chasing mountain roads, sunrises, and experiences that most people only dream about.
Somewhere along the way, something unexpected happened.
The motorcycle was changing… But so was I.
I started filming more. Sharing my rides. Telling stories.
What began as a way to document adventures slowly grew into the community that would eventually become Rips Unfiltered.
Looking back now, “Gnarly Glide” wasn’t just a custom motorcycle.
It was the bike that gave me the confidence to put myself out there.
To create. To travel farther. To dream bigger.
To realize that maybe this passion could become something much more than a weekend hobby.
It also taught me something I’ll never forget.
No matter how beautiful a motorcycle is… The memories you create on it will always matter more than the parts bolted onto it.
Favorite Memory: Traveling cross country, solo, most notably from Florida to Arizona three days after she was built.
Lesson Learned: Build the motorcycle that makes you smile. Trends fade, opinions change, but riding a bike that feels like an extension of yourself never goes out of style.
🏍️ Bike #7: 1997 CMC Chopper
The Chapter: Some Things Can’t Be Bought
What It Taught Me: The Best Motorcycles Carry Memories
This motorcycle was never about horsepower. Or handling. Or comfort.
In fact… It’s probably the least practical motorcycle I’ve ever owned.
And I absolutely love it.
This 1997 CMC Chopper was an engagement gift from Russ.
Out of every motorcycle that’s come and gone through my garage, this is the one that carries the most sentimental value.
It isn’t the bike I grab for a thousand-mile road trip.
It isn’t the bike I’d recommend for a cross-country adventure.
It’s the bike I ride when I want to slow life down and remember why I fell in love with motorcycles in the first place.
Every time I throw a leg over it, I’m reminded that motorcycles aren’t always about where you’re going.
Sometimes they’re about who gave them to you.
This chopper represents an entirely different chapter of my life.
One built on love, partnership. And sharing a passion with someone who understands why disappearing on two wheels every now and then is good for the soul.
The truth is… Motorcycles come and go.
I’ve bought them. Sold them. Customized them. Ridden them across the country.
But this one?
I don’t think it’ll ever leave my garage.
Not because it’s the most valuable motorcycle I own.
Because it’s priceless to me.
Favorite Memory: The moment Russ surprised me with it. Some gifts are unforgettable, not because of what they are, but because of what they represent.
Lesson Learned: Sometimes the motorcycles with the fewest miles carry the biggest piece of your heart.
🏍️ Bike #8: 2026 Harley-Davidson Road Glide “Rogue”
The Chapter: Hard Work Has a Funny Way of Paying Off
What It Taught Me: Keep Showing Up
There are phone calls you never forget.
When Harley-Davidson called and told me they wanted to gift me a brand-new Road Glide, I honestly thought someone was playing a joke on me.
Seriously. Me?
I’m not a full-time influencer. Half the time I feel like I’m struggling just to keep up with regular content.
But little did I know…
Years of motorcycle adventures, custom bike builds, thousands of miles on the road, and simply sharing my story hadn’t gone unnoticed.
That phone call wasn’t about one video.
Or one motorcycle.
It was the result of years of showing up.
The day I picked Rogue up, I didn’t take her home.
I drove straight to Manic Cycles in West Palm Beach. Because this wasn’t going to be an ordinary Road Glide.
She was about to get the royal treatment.
A complete frame-off build.
Custom components from some of the best companies in the industry.
And… My very first turbo.
Of course, I didn’t just want a beautiful motorcycle.
I wanted a motorcycle that performed as well as it looked.
Every decision we made during the build had those two goals in mind.
When Rogue debuted less than two months later at Daytona Bike Week in 2026, I was incredibly proud of what our team had created.
Then something happened I never expected.
She took home Best Bagger at the V-Twin Visionary Show.
Standing there looking at that motorcycle, it wasn’t the award that hit me.
It was everything that happened before it.
The scared eighteen-year-old learning to ride in her neighborhood.
The Hayabusa.
The Road Glide that made me fall in love with touring.
Gnarly Glide.
Every motorcycle before Rogue had quietly led me to this moment.
She’s still one of the newest additions to my garage, and I have a feeling we’re only getting started.
Big adventures are already on the calendar.
If the first chapter of Rogue’s story taught me anything…
It’s that the best rides are still ahead.
Favorite Memory: Watching Rogue roll onto the stage at Daytona Bike Week and realizing a dream I never knew was possible twenty years earlier.
Lesson Learned: You never know who is watching. Keep doing the work, keep telling your story, and let your passion speak louder than your expectations.
🏍️ Bike #9: 2025 Indian Challenger “Chalk”
The Chapter: Betting on Myself
What It Taught Me: The Best Stories Rarely Go According to Plan
Out of every motorcycle that’s been parked in my garage, Chalk is the one I never would’ve imagined owning.
If I’m being honest, I was skeptical.
The Challenger had a fantastic reputation for performance, but aesthetically it just wasn’t a motorcycle I had ever pictured myself riding. Styling is personal, and at first, it simply wasn’t my thing.
Then Indian Motorcycle offered me the opportunity to spend a year with one.
Some people assumed I was switching sides. Not even close.
This wasn’t about Harley versus Indian.
It was about motorcycles.
I’ve always believed that if you’re fortunate enough to have the opportunity to experience different motorcycles, different platforms, and different riding styles… why wouldn’t you?
I’m not a Harley rider.
I’m not an Indian rider.
I’m a motorcycle rider.
I picked Chalk up from Music City Indian in Nashville, TN. and immediately rode to Forever Rad in Hillsboro, MO.
If I was going to spend a year on this platform, I wanted to give it a fair chance. That meant building it into something I had been accustomed to riding. Kyle and the crew transformed the bike into something incredible, and during the reveal we spent hours going over every modification, every bolt, and every decision that went into the build.
I wanted to understand the motorcycle just as much as I wanted to ride it.
I had big plans for Chalk.
My thought process was simple…
If a manufacturer is willing to trust me with one of their motorcycles for a year, then I’m going to give them the most honest review I possibly can.
And in my world… The best review isn’t written.
It’s ridden. A LOT.
Then one day, an idea that sounded completely ridiculous became a plan.
Ride all 48 contiguous states in six days.
People asked me if I was nervous.
Of course I was.
But I was even more excited to find out whether I was capable of pulling off something that seemed almost impossible.
Together, we crossed the country, raised money for Quantum House, and proved that sometimes the craziest ideas are worth pursuing.
Unfortunately, our journey wasn’t perfect.
An aftermarket part failed the morning of Day 5 forcing Chalk to the sidelines.
I’ll never forget looking back at her sitting there in the New Mexico desert. I missed that motorcycle more than I expected over those final two days.
Even though another Challenger helped me finish the ride, it wasn’t my bike.
When people ask me about setting the women’s record for riding all 48 contiguous states in six days, they usually expect me to talk about mileage.
Or exhaustion. Or sleep deprivation.
Instead…
I talk about people.
The strangers who stopped to check on me. The companies that worked behind the scenes. The friends who never stopped believing.
The motorcycle community that reminded me I was never riding alone.
That’s what I’ll remember most.
Chalk helped me become the fastest woman to ride the lower 48 continuously in six days.
But that’s not why she’ll always have a place in my heart.
She reminded me that when things don’t go according to plan…
Sometimes they become an even better story.
🏆 World Record Motorcycle
Favorite Memory: Walking into the Forever Rad compound for Chalk’s reveal and spending hours with Kyle going over every detail of the build. It wasn’t just about making the bike beautiful, it was about understanding the platform before asking it to do something extraordinary.
Lesson Learned: Great accomplishments are never achieved alone. Behind every finish line is a community of people who believed in you long before you believed in yourself.
Closing Thoughts
Looking back at these motorcycles, I don’t just see chrome, horsepower, custom paint, or performance parts.
I see the different versions of myself they carried along the way.
The terrified eighteen-year-old trying to figure out a clutch.
The college kid who somehow convinced herself a Hayabusa was the logical next step.
The young mom who stepped away from riding for a while, only to discover that the road had patiently waited for her return.
The rider who learned that slowing down wasn’t giving up, it was finally learning to appreciate the journey.
The traveler.
The storyteller.
The woman who stopped wondering if she was capable and finally started believing she was.
Every motorcycle in this garage represents a chapter of my life. Some chapters lasted years. Others only a season. But every single one left its mark on me.
People often ask me what my favorite motorcycle has been.
The truth is… I don’t think I have one.
Each bike gave me exactly what I needed at that point in my life. Some gave me confidence. Others humbled me. Some carried me through heartbreak, while others helped me celebrate life’s biggest victories. Together, they’ve created a collection of memories that no amount of chrome or horsepower could ever replace.
If there’s one thing I’ve learned over the years, it’s this:
Motorcycles don’t just take you places.
If you let them…
They change you.
They introduce you to people you’d never have met.
They teach you lessons you never expected to learn.
They become part of your story in ways you don’t realize until years later, when you look back and see just how far you’ve come.
I have no idea what motorcycle will become Chapter 10.
But if these first nine have taught me anything, it’s that the best adventures are usually the ones you never saw coming.
When I think back to that twelve-year-old girl staring out the window of my mom’s Ford Explorer, watching an older biker sitting at a stoplight, I smile.
She had no idea that one passing moment would shape the rest of her life.
She couldn’t have imagined riding across the country alone.
Building custom motorcycles. Creating Rips Unfiltered. Meeting so many incredible people. Or becoming the fastest woman to ride the lower 48 states in six days.
She just knew one thing…
She wanted to know what it felt like to ride.
I’d like to think she’d be pretty proud of how this story has unfolded.
And somehow…
I think she’d still be dreaming about the next ride.
Thank you for taking a ride down memory lane with me. I hope somewhere in these stories you found a piece of your own.
Here’s to the next chapter. The next motorcycle. The next adventure.
Until then…
The Rips are out.