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Man finishes bike ride from one Portland to another

Chris Winkler is from Portland Oregon, and on an adventure that lasted 69 days and well over 3000 miles, traveled from the coast of Oregon to the coast of Maine.


On June 12th, 2021, Chris and Cheryl Winkler from Portland, Oregon, set out to complete a journey from the coast of Oregon to the coast of Maine. To make the adventure more unique, Chris traveled the distance from Portland, Oregon to Portland, Maine entirely by bike.  

As Chris pedaled, Cheryl drove an RV dubbed  “The Jamboree” or “Jambo” for short. 

“The Jamboree has been our home since June 11th and every night we stop. He's done it continuously. He starts exactly where he’s stopped the previous day,” Cheryl Winkler said. 

Sixty-nine days later and well over 3,000 miles traveled, Chris arrived at the coast in Portland’s Eastern Promenade to be surprised by his family there to cheer his accomplishment.  

“It’s kind of emotional. This is all a surprise that the kids are here,” Cheryl said. 

“They surprised me... Typical as my family is, they are amazing,” Chris said. 

After the cheers and a big group hug, Chris brought his bike down to the shore to complete his Coast to Coast and Portland to Portland challenge. 

When asked what he enjoyed the most from his journey, Chris talked about the people.  

“Meeting the people of the country I think was probably the biggest. Cheryl and I talked about all the time, in Eastern Montana and South Dakota and Minnesota and Wisconsin, some of those small rural areas we made a point to go into the restaurants and talk with the people," he said. "There are some great people out there. And then the people who joined me along the way. It was just so much fun to be riding with them, getting some personal time with people on the road. Working hard together. That was all really really fun.” 

And when asked how he was planning to go back... 

“So the RV is what got us here. Riding and then staying in the RV and just going. Now we’re going to put this baby up. Put it on the bike rack and drive back,” Chris said. 

If you’d like to check out Chris Winkler’s blog, “1k to the Bay,” where he documented each day of his Coast to Coast and Portland to Portland bike ride, you can go to 1ktothebay.com.

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