From Passenger to Rider: How I Conquered My Fear and the Highest Peak in Massachusetts

I started my motorcycle journey as what we affectionately call a “backpack”— just a passenger hanging on. My first real ride was back in 2003, when I joined a trip up to Lake George, New York. I remember thinking, “There’s no way I could ever ride my own motorcycle.” But there was one woman in our group who rode a Harley Switchback, and I was totally inspired. Watching her, something inside me clicked: “I can do this. I can do this. I can do this.”

Eventually, I decided to stop letting fear hold me back. I went and got my motorcycle endorsement. My first rides on that little 250cc bike were rough —panic attacks, tears, full-blown anxiety. But one day, I got on Route 36, and suddenly I heard this voice in my head say, “Girl, you got this.” From that moment on, I knew I was exactly where I was meant to be.

Some of my most memorable rides were with my brothers, Brian and Bill — though this particular time, it was just Brian and me. We took a trip up to Mount Greylock, the highest peak in Massachusetts. Let me tell you, I had no idea what I was in for. I was riding along when I saw a sign that said, “Hairpin Turn Ahead.” My heart dropped. I started panicking — “No, no, no, no, no!” But it was too late to turn back. I took the turn wide and saw a car coming the other way, but I cleared the turn. I barely had caught my breath when I saw another sign that said, “Another Hairpin Ahead.” My nerves were shot but somehow, I made it to the top.

When I finally pulled off my helmet, I was in tears — just overwhelmed by everything. Brian came over and said, “You did it. You made it. We’re up here. You’re okay.” That moment — his calm, his pride — it meant everything. We sat at the top for a while, took in the views, and tried to relax. At least the rain had stopped.

Eventually, it was time to head back down. Most of the group went on ahead and waited for us at the base. Brian led the way, I rode in the middle, and someone else rode sweep behind me. Not one car came up behind us the entire way down. I took the first hairpin carefully, and by the second one, I actually started to feel excited. When we got to the bottom, everyone was cheering. They were so pumped for me. I was proud. Exhausted, but proud.

Later, I told Brian, “I really didn’t want to go back down that mountain.” And he looked at me and said, “I wasn’t going to tell you this before, but if you really couldn’t do it, I would have taken you down. I would’ve had someone ride back up to get your bike. I would’ve handled it.” That’s the kind of brother he is. Both of them, honestly. I have the best brothers in the world.

That ride didn’t just test my skills — it tested my courage. It reminded me that fear is real, but so is determination. I’m not just a former passenger anymore. I’m a rider. A real one.