Overland | The Eyes Up Ride
Heading up Rollins Pass in Colorado with Riley Frackleton. October, 2021.
Originally published as part of the Overland Summers Blog
I started seriously thinking about riding cross-country in January 2021. I had a feeling I was in my final year on the Overland year-round staff and knew this would be the first time in my life where I truly had a blank canvas of time to work with. For my whole life, my dad’s cross-country bike trip in 1977 was this sort of abstract dream that never felt like a tangible reality - the kind of thing that felt so out of reach I never seriously considered doing it. While working for Overland, I became entirely swept up in the incredible cycling community and grew to love spending my weekends on rides. I became a stronger cyclist and my confidence in longer rides grew quickly. So, as I began to daydream about my post-Overland life, I made the mental hurdle of seriously considering riding cross country. The idea sat well with me and felt good and exciting, so I continued to brainstorm. It didn’t feel quite right to be going out on this adventure purely for my own experience. I wanted to have a deeper meaning while riding to give me purpose and keep me motivated.
I texted the executive director of TextLess Live More, Marie McGrath, on January 31st to float my then-nebulous idea of riding my bike across the country to raise awareness for distracted driving and fundraise for TextLess Live More. When I got a text back from Marie with excitement, I knew this was the right path forward for me. From there, the concept turned into a rough route from Cape Cod, Massachusetts to Seattle, Washington that hit three must-see landmarks: Niagara Falls, Kenyon College, and Portland Oregon (to see my sister). Then came a snowball of ideas for my route, which quickly changed from 4,300 miles to 10,000 miles, a website, logo, Instagram, and fundraising campaign. It began to feel more real - I found a bike online and it arrived at my house. My dad even had it blessed by a priest in Connecticut when I had it built down there. Things were put on pause for the Overland summer, where operations are essentially 24/7 for about nine weeks.
There were eight days between the end of the Overland season and the start of my ride. In those days, I moved out of my apartment in Williamstown and put everything in my parents house, flew to and from California for a family event, packed my bike with everything I needed for the next three months, drove to Provincetown, Massachusetts with my parents and bike, and started my journey. In that time, I also reached my original fundraising goal of $10,000. From that point on, life was stripped down to the sweetest trio of essentials: eating, riding, and spreading awareness for a cause I care a lot about.
Since August 21st, I have ridden my bike 5,208 miles across 16 states. I have met countless people ranging from remotely curious as to why I am riding my bike in their town to folks deeply connected to distracted driving and incredibly grateful for what I am doing. I cannot summarize in a blog post all of the amazing things I have seen and experienced on my trip so far, but I can say that the United States is a vast place filled with the kindest souls imaginable. I have nothing but gratitude for the dozens of people who have helped me, for the folks at TextLess Live More who have helped me get here, and for the opportunity to be riding for an important cause and sharing the mission with this country.
I am back home in Connecticut for the next month - resting, stretching, and working hard to fundraise while I have the time and bandwidth for more extensive outreach. In mid-January, I will get back on the road where I left off - Raymond, Washington, and head south to San Diego. From there, I will turn hard left toward Jacksonville, Florida. By trip-end, I aim to have raised at least $50,000. Follow along and consider supporting this cause at EyesUpRide.com/support.
