A 2,200-mile, 45-day bike ride through grief and toward meaning

Grief can make the world feel smaller. For 23-year-old Rory Perlow, it did the opposite — presenting itself as 2,200 miles of open road.

After losing two close friends, the Highland Park native committed to a 45-day, cross-country ride beginning Monday, June 1, while raising awareness and funds in support of mental health services.

Perlow said his journey is his manifestation of misogi, a concept of Japanese origin meant to enable clarity and purification through a difficult and life-altering challenge. Somewhere between the start and the finish of his journey, he hopes to find a clearer sense of purpose, while raising money for a good cause.

Backstory

Before biking, Perlow was a competitive wrestler. He competed on the national stage multiple times and was the state runnerup in his weight class (132 pounds) his senior year (2021) at Deerfield High School.

Cycling, though, has always been there. His mom is a professional cyclist, and Perlow worked at Deerfield Cyclery during his summers home from college. And he’s long considered himself a casual cyclist.

This past year, after two of his friends passed away, Perlow had a breakthrough.

“I saw how that changed me,” Perlow said. “I realized that all this time isn’t to work to live, rather it’s to live to live. Do what inspires you and in the byproduct of that, your life will surround it.”

In an effort to get closer to that purpose, Perlow learned about misogi and wanted to embrace it, to do something life-altering for his new year’s resolution.

“I didn’t know what it was, but I wanted to do it,” Perlow said.

Equipped with a no-quit attitude reinforced for years by his wrestling and cycling coaches, Perlow had his mind set on accomplishing something big.

“If I put myself in an environment where I can’t really quit, I’m just going to have to push forward,” he said. “The only way I know how to rebuild something real is to do the hardest thing I can think of and do it out loud.”

His version of that was an arduous, cross-country bike ride.

The ride

From Chicago to Santa Monica, a span of 2,200 miles, over a period of 45 days starting June 1, Perlow will bike Route 66 solo.

“I knew I wanted to ride across the country,” Perlow said. “It was almost an impulsive thought I had, but I knew I needed to do it — something just felt right about it.”

“I know it’s going to be challenging,” Perlow added. “But if I can stay optimistic about the ride, the word it’s going to spread, and the people I will meet along the way, I think it’s going to work out very well.”

The trip has been in the works for three months, and Perlow has been training for two and a half months. His training includes roughly 30 to 60 miles of biking every day, with the guidance of his coaches at Vision Quest in Highland Park.

He estimates riding 50 miles each day, which will amount to approximately six to eight hours on his bike. He will carry 30 to 40 pounds of gear, including bike parts, extra tires, camping gear and camera equipment.

Perlow will stay overnight at campsites and national forest preserves and plans to cycle with cycling groups in larger cities.

Challenges, he said, will be riding in the Oklahoma, Texas and southwest Missouri wind, and pushing through 150 miles of dark desert from Arizona to California in the early-morning hours.

Perlow plans to stay prepared for bad weather, mechanical issues or exhaustion that may arise as much as he can. For events he cannot plan, he will take a day off and extend his trip to over 45 days, if necessary.

His journey will begin at Chicago’s Navy Pier, which recently held a 100-year celebration of Route 66, a “pier-to-pier” connection linking Lake Michigan to the Santa Monica Pier.

Perlow’s family, friends and more will be there to support him starting at 10 a.m. June 1 at Navy Pier, where he will talk about his ride and the Jed Foundation prior to his departure. The public is welcome to attend his takeoff event.

The message

Perlow gave credit to his mother and father, his cycling coaches at Vision Quest Coaching in Highland Park, his boss at Deerfield Cyclery, and friends who all have been there to support his journey.

Perlow hopes his trip will “inspire” others to talk about what they are feeling, even if it’s difficult, and take on something challenging of their own, he said.

His message is about “being able to do what you set your mind to do” and developing good habits, which he believes everyone is capable of doing, he said.

Perlow’s ride will be livestreamed on Kick and documented daily on Perlow’s TikTok and Instagram at @its.justrory. He will share the livestream link and ways to donate on those social-media channels.

“Livestreaming the whole thing will allow people to tune in all the time,” he said. “So, they can feel that they are a part of it themselves.”

Along the way, he will be raising money for the Jed Foundation, a nonprofit that protects emotional health and prevents suicide for teens and young adults.

Perlow’s goal is to raise $45,000 during the 45-day trip.

“I have a very strong emotion around expressing youth mental health, and supporting the Jed Foundation is one of the ways I can do that,” Perlow said, adding “Hopefully, with the livestream and content I am putting out on my socials, along with the support of my family and friends, we can raise $45,000 to an organization that needs it.”

The Record is a nonprofit, nonpartisan community newsroom that relies on reader support to fuel its independent local journalism.

Become a member of The Record to fund responsible news coverage for your community.

Already a member? You can make a tax-deductible donation at any time.