‘The Hardest Thing I Could Think Of’: North Shore Man To Bike Route 66 Solo

DEERFIELD, IL – Rory Perlow is about to spend 45 days alone on a bike, crossing eight states on Route 66 from Chicago to Santa Monica.

For the Deerfield native, the ride is not just an endurance test. It is a response to grief, a public challenge to himself and a fundraiser for youth mental health.

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“This past year I lost people I loved,” Perlow tells Patch. “The kind of loss that stops everything cold and forces you to take a hard look at what you’ve actually been doing with your time.”

Perlow, a former Deerfield High School wrestling standout who now lives in Highland Park, says that loss forced him to rethink the way he had been living.

“What I realized is that I had been living to work,” he says. “So I had to make a different choice. I had to start living to live.”

Rory Perlow

That choice became a 2,200-mile solo bike ride with no crew and no support van, beginning June 1. Perlow plans to livestream the ride on Kick, post updates on TikTok and Instagram, and raise money for The Jed Foundation, a nonprofit focused on youth mental health.

“It’s the hardest thing I could think of to do, and it’s the most public way I could think of to do it,” he says.

The Jed Foundation, commonly known as JED, is a New York-based nonprofit focused on protecting emotional health and preventing suicide among teens and young adults.

The organization works with high schools, colleges and youth organizations across the country on mental health awareness, suicide prevention, emotional resilience and helping young people connect to support systems before they reach a crisis point.

Perlow says the discipline behind the ride was shaped long before he fully committed to cycling. He was introduced to wrestling by his father, placed at nationals more than once, finished as Illinois state runner-up his senior year at Deerfield High School and later attended the University of Iowa.

“Trophies aren’t the part I carry with me,” Perlow elaborates. “What I carry is the discipline, the people who shaped it, and the truth that when it gets hard, you don’t quit.”

He credits Deerfield coaches Mark Pechter and Aaron Cohen with helping shape that mindset, while injuries taught him how to rebuild when progress was uncertain.

Cycling also has deep roots in his life. Perlow says his mother first got him into biking, and the sport became a bigger part of his life while he worked at Deerfield Cyclery for several years.

“The biggest thing I took out of those years was Greg Balmes, who owns Deerfield Cyclery,” Perlow says. “Greg is one of the most inspirational people in my life.”

According to Perlow, Balmes taught him lessons about integrity, work and how to show up for people.

Perlow says he did not fully commit to cycling until recently, when “something shifted” and the sport found him in a new way.

He has been training at Vision Quest in Chicago with Robbie Ventura and Dave Noda, along with riding on his own most days. A recent 100-kilometer race helped convince him his body could handle the distance ahead, he said.

“The fitness is in. The work has been done,” Perlow says. “The last stretch is about not breaking myself before the ride starts.”

For Perlow, the route matters less than the act of finishing it.

“Santa Monica is the end point, but Santa Monica isn’t the point,” he says. “Making it to Santa Monica is the point.”

Perlow hopes the ride speaks to young people dealing with grief, isolation and other struggles they may feel pressured to carry alone.

“What I want kids to know is that they don’t have to go through hard things alone,” Perlow says.

That is one reason he chose to make the ride so public.

“If I quit halfway, everyone watching is going to see me quit halfway,” he explains. “That fear is a feature of the ride, not a bug.”

For Perlow, the goal is bigger than reaching the Pacific. It is about showing, mile by mile, that hard things can be faced in the open, a lesson shaped years ago in Deerfield wrestling rooms and at a hometown bike shop.