By Tony Madden
Nearly 18 years after hitting a low point, former radio host and news anchor Debbie Jackson has set off on her first cross-country bike ride from San Diego to San Augustine, Florida. Currently, she is bicycling her way across New Mexico.
In 2008, Jackson, a Belton native found herself on the brink of despair. After a traumatic situation, she found herself asking, “God, what do I do?” Jackson said the answer was clear.
“Debbie, ride your bike,” she heard.
The voice was confusing at first. Then, a memory from Jackson’s childhood made things clear.
The message rekindled Jackson’s old childhood dream of riding her bike across the continental United States. That dream began at age 12, when Jackson picked up a book on cross-country cycling. However, “life happened,” she said, discussing her illustrious careers as KCMO radio host and as founder of the local Coffee News.
When the time came to finally prepare for such a trip, Jackson didn’t know where to start. But she remembered the adage, “A trip of 1000 miles begins with one step.” So, she took the step — a few steps actually — into the basement, where she aired up the tires on her old mountain bike.
Then, she got more people involved. She began riding annually in Bike MS: Kansas City, a fundraiser that benefits the National Multiple Sclerosis Society. That got her connected with local cycling groups, who prepared her physically and mentally for a cross-country ride.
Now 63, Jackson dipped the back tire of her pink Specialized Vado SL bicycle into the Pacific Ocean at Dog Beach in San Diego on March 5. Then, she started riding east. Roughly 3100 miles later, she’ll dip her front tire into the Atlantic Ocean in San Augustine, Florida.
Jackson will travel an average of 66 miles per day, six days per week, for two months across eight states on a tour led by Woman Tours. That daily distance is an average, Jackson said, pointing out that one leg of the trip is 119 miles long. About 17 days of the trip will be spent crossing Texas alone, she added.
“I don’t know how,” Jackson admits. But that is where additional cyclists come in.
Woman Tours, based in upstate New York, is leading Jackson’s all-female tour group. The average age of riders is about 65, Jackson said. While some riders camp by the side of the road, Jackson will stay in hotels and short-term rentals set up by Woman Tours. The group will also travel with a personal chef to make sure the team is properly nourished.
“It’s a bunch of grandmas riding across the country,” Jackson said with a laugh.
Woman Tours will also provide Jackson’s team with support vehicles in case of emergencies or if a rider needs to be driven to the next location.
When she felt moved to ride her bike again in 2008, Jackson said it didn’t make any sense. She had kids. She had a job. She wasn’t, as she saw it, a cyclist. But in 2026, things will be different. Jackson is semi-retired with a lot more time, and she has no more kids living at home. Now, she wants to inspire others to pick up a bike — even a metaphorical one.
“I highly suggest it, or also just any dream,” Jackson said. “When I say, ‘Ride your bike,’ I don’t just mean a bike. I mean do whatever is your dream. And even if you thought of it a long time ago, don’t give up on it.”
That hunger to inspire others manifested itself online as Jackson documented preparations for her cross-country ride. Family, friends and community members can follow Jackson across the United States on her Youtube channel, aptly titled “Debbie Ride Your Bike.”
“It is my hope this channel informs, encourages, and inspires anyone who wants to do a cross country bike ride or reach for any dream,” Jackson writes on her channel.
Jackson’s family and friends have been a profound source of inspiration as she prepared for the trip. She thanks her two adult sons, Alex and Joey, for taking care of things at home while she’s gone.
Jackson also diligently followed a training schedule created by her seven-year-old grandson Slade, who has been her “little coach.” When she began experiencing elbow pain from overuse, Slade reminded Jackson she needed to stretch more often. At the end of the day Slade is who Jackson remembers while riding her bike.
“I didn’t have a cute little grandson when I came up with all this stuff, when God told me,” Jackson said. “But he’s seven years old and we’re super close, so it’s gonna be difficult to be away from him for two months.”