Fifteen years ago, Chuck Bolton set out on a personal mission—one that would unknowingly become a movement. What began as a bike ride to clear his head and reclaim a sense of freedom during a difficult time in his life has evolved into the annual Ride 2 Rosemary®: a 525-mile cycling journey from Memphis to Florida that embodies brotherhood, healing and a shared commitment to fighting cancer.
Chuck never intended to start a tradition and, in fact, it was others who took his idea and made the event what it is today. In 2010, when two of his closest friends, Todd Tillmanns and Keith Merriman, visited him and asked what he planned to do following a particularly challenging period in his life, he simply replied, “I’m getting on my bike and riding to Florida.” Their response was immediate: “We’re in.”
That first ride wasn’t about fundraising, finish lines or fanfare. It was about freedom, faith and friendship. But as the ride took root and more men joined, it became clear that this wasn’t just a personal journey—it was a powerful community built around connection, vulnerability and purpose.
“This ride is about knowing each other deeply, loving each other well and walking through life’s highs and lows together,” Chuck explains. “It’s about becoming healthier men, husbands and fathers, and inviting others into that transformation.”
The Ride 2 Rosemary crew is diverse in age, background and faith journeys. Some are in recovery, like Chuck, who has been sober for 19 years. Others are simply seeking a deeper connection—with themselves, with others, or with God. What unites them is a shared commitment to growth, accountability and authenticity.’
Over the years, the ride has taken on even greater meaning. After several of the men experienced personal losses to cancer—including Chuck’s mother, mother-in-law, as well as close friends—the group decided to dedicate their efforts to raising awareness and funds for West Cancer Foundation.
“Cancer touches everyone,” Chuck says. “Supporting West Cancer Foundation was a natural fit. It’s where many of us—and so many in Memphis—turn for hope and healing.”
What began as a spontaneous ride among nine friends has become a purposeful pilgrimage, rooted in compassion. Today, the Ride 2 Rosemary team includes cancer survivors, men in recovery, elite cyclists and those who’ve never attempted anything like this before but have a passion for cycling. No one gets left behind. Stronger riders place hands on the backs of others, pushing them forward—literally and symbolically.
The ride isn’t just about the road—it’s about the moments in between, late-night story sharing, laughter and quiet prayers in small towns. It’s about a collective promise to be “real” with one another and to welcome everyone—regardless of where they are in life or in faith.
And while the ride has grown in impact and participation, one thing remains the same: “This isn’t a competition,” Chuck says firmly. “It’s not about who raises the most money or rides the fastest. It’s about community. And every man who joins is valued equally.”
Chuck has experienced his share of heartbreak along the journey. In 2022, his son went missing and was later found deceased after 57 days. The men of Ride 2 Rosemary formed search teams and stood by Chuck’s family in their deepest grief—just as they did for Richie Fletcher whose wife, Eliza Fletcher, was lost that same year.
“The brotherhood is real,” Chuck says. “They showed up when we needed it most.”
As Ride 2 Rosemary marks its 15th anniversary, Chuck isn’t sure how many more years he’ll ride. At 63, with rods in his back and a growing family to enjoy, he knows there will come a time to pass the torch. But one thing is certain—he’ll never be far from the movement he started.
“I’ll always be part of this ride,” he says. “Even if I’m in the support van or standing at the finish line with tears in my eyes, watching the next group of men arrive.”
To Chuck, the ride is more than a route on a map. It’s a path to purpose, healing and connection. And for West Cancer Foundation and the thousands of cancer patients it serves throughout the Mid-South, it’s a symbol of what’s possible when people come together with love, faith and a mission to make a difference.
