Four bicycles, 3,640 miles: TD grads take kids on cross-American adventure
By Tom Peterson
All photos courtesy the Smith family
EADS, Colo., July 30, 2026 — Five bicycles. Three children. More than 1,350 miles behind them. More than 2,000 miles still to go.
After 33 days on the road, Craig and Melinda Smith, both graduates of The Dalles High School, and their three children rolled into the eastern Colorado farming community of Eads on Wednesday, July 29, leaving the Rocky Mountains behind as they continue a 3,800-mile bicycle journey from Walla Walla, Washington, to Yorktown, Virginia.
Starting off in Walla Walla on June 22. Melinda Von Borstel Smith and son Josiah are sharing the tandem bike while Emilia, Isabel and Craig are solo.
The ride is testing the family physically and mentally, but it is becoming something far greater than a cross-country bicycle trip. Along the way, the Smiths hope to discover America one back road at a time, strengthen the bonds of their young family and raise money for a Pacific Northwest nonprofit serving at-risk youth.
"We've learned to ask one question," Smith said during a telephone interview Wednesday evening. "'What do we need to do today?' If we look beyond today, it does not end well."
That simple philosophy has carried the family over 11,540 foot Hosier Pass just days ago, through forests of Idaho, Montana and West Yellowstone, onto the vast High Plains of eastern Colorado, where the towering peaks have given way to endless horizons, wheat fields, steady winds and summer heat.
Cooling off near Lolo, Mont.
"It's tougher on the adults for sure," Smith said with a laugh. "But it has been fun to watch the kids grow in the journey."
The family averages about 40 miles each day, usually taking one rest day each week while covering between 280 and 300 miles. They expected to cross into Kansas on Thursday, another milestone in a journey they hope to complete in about 90 days.
Yet Smith said the biggest challenge isn't climbing mountains or battling the heat.
"The long mental haul," he said. "When you get into it for a while, it gets tough. It's as much a mental thing as a physical thing at some point."
Ironically, that challenge has become one of the greatest rewards.
"It forces you to be here and now," Smith said. "There's an overlap between long-distance backpacking and touring. The world becomes much more simple."
A family adventure
The journey began June 22 when Craig, a 1998 graduate of The Dalles High School, and Melinda, a 1999 graduate, left Walla Walla with their three children — Emilia, Isabel, and Josiah — on a 3,640-mile ride across the United States along the historic TransAmerica Trail.
The family expects the journey to take about 90 days.
The adventure did not begin without preparation - the family actually utilized several portions of the bike trail to train on before starting.
Touching the Pacific Ocean, Emilia, Isabel, Josiah, Melinda and Craig as they prepared for their transcontinental journey.
Earlier this year, the family completed a series of increasingly ambitious training rides, including a 140-mile trip from Beaverton through Government Camp to The Dalles for the wedding of Smith's niece, Emma; a 200-mile round trip from home through Vernonia to Astoria and back; and a ride from Seaside to the Astoria Column and back.
Together, those rides totaled roughly 260 miles before the family completed one final 160-mile "shakeout ride" from The Dalles to Walla Walla.
"The purpose is simple," Smith wrote before departing. "Find the remaining problems before the real journey begins. Better to discover those realities in the relative confines of eastern Oregon and Washington than somewhere in the middle of America."
More than a bicycle ride
Emilia, Isabel, Josiah provide the vision of their journey early with their portrait of the road ahead, pointed with the Sunset at Seaside, Oregon and the sunrise at Yorktown, Va.
While the cross-country ride is creating lifelong memories for the Smith family, it is also serving as a fundraiser for Braking Cycles NW, a Pacific Northwest nonprofit that mentors and supports at-risk youth through housing, vocational training and community programs.
The family launched a "Penny Per Mile" campaign, asking supporters to donate one penny for every mile of the 3,640-mile journey. A full pledge totals $36.40, with all proceeds benefiting the nonprofit's work with vulnerable youth.
For Braking Cycles, the penny carries special meaning.
"Pennies are much like the youth we serve," the organization explains. "They are tossed aside, stepped over, forgotten, and not valued."
That symbolism inspired the nonprofit to install a floor made from thousands of pennies inside its Coffee & Bike Shop, representing the value and potential it sees in every young person.
"With thousands of at-risk youth in Oregon and Washington, we want to expose the lies that say they do not hold value by giving them an opportunity to shine through our housing, mentorship and vocational programs," the organization states.
Smith said his connection to Braking Cycles came through Lauren Hutchinson, a member of his financial planning team whose volunteer work introduced him to the organization. His shared interests in cycling, coffee and serving others made the partnership a natural fit.
Breaking cycles
Smith said the journey is about far more than riding bicycles.
Earlier this year, he reflected on what he called the "true purpose" of money.
"My answer was simple: Family," he wrote. "Not consumption for consumption's sake. Not status. Not accumulation as an end unto itself. Family. Experiences. Time. Shared struggle. Shared victories. Memories."
He hopes the trip teaches his children that difficult things are possible, that ambitious goals can be pursued imperfectly and that "someday" can become "today" if someone is willing to begin.
Watching his children adapt to life on the road has become one of the greatest rewards.
"It is fun to watch the kids grow in the journey," Smith said. "Every day is the same, but different. We transitioned from mountains to more prairies, and now it's more wind and heat instead of climbing."
For Smith, the phrase "Braking Cycles" has also taken on a personal meaning.
"It's the idea of breaking cycles," he said. "I've got my own cycles — working too much and not being present enough. This is a chance to be present with them ( Melinda and the kids).
As the family pedals east toward Kansas, the finish line in Yorktown remains well over 2,000 miles away.
For now, Smith said, the goal remains simple.
Just make it to the next town.
Then do it again tomorrow.
Follow the journey
Readers can learn more about the Smith family's Penny Per Mile Challenge benefiting Braking Cycles NW at:
Braking Cycles NW – Biking Across America to Aid At-Risk Youth
Follow the family's daily photos and updates on Instagram:
Track the family's progress across the country on their live GPS map:
Follow My Challenge – Smith5 Braking Cycles
Read Craig Smith's longer reflections about the adventure on his Substack:
CCCNews will periodically check in with the Smith family throughout their cross-country journey, bringing readers updates as they continue pedaling toward Yorktown, Virginia.
