Harley-Davidson launched the contest to see what fans had gotten up to during lockdown.
People were asked to show off their bike paint jobs and hair cuts.
Paul Brothwood, aged 38 from Kingswinford, in Dudley, had Mexican themed artwork painted onto his Heritage Classic by illustrator Matthew Sharpe.
Mr Brothwood is the assistant director of the Wolfruna Harley Owners Group Chapter, which is planning a tour of Europe in the future.
He said: "Lockdown has been a challenge for us all.
"As I was not able to ride my bike, I took the opportunity to have it fully customised.
"The artwork is inspired by Frida Kahlo [Mexican theme] and thanks to social media I was able to find an artist that could assist.
"I very much look forward to touring Europe if allowed in the summer. My chapter has a route mapped out to Moscow, which we are all very excited about."
As part of the competition, the top four photos were chosen and put to a public vote via social media.
Mr Brothwood receievd a flurry of votes for the artwork and has won a Harley-Davidson helmet, which we will also have painted by Mr Sharpe.
Mr Sharpe said: "It was great to work virtually and create such a unique piece of art. To have national recognition like this is exciting."
Paul Lilly, market leader for Harley-Davidson UK and Ireland said: "We wanted to create a fun and engaging opportunity for our community to share examples of what they’ve been up to during lockdown, be that suspect DIY home haircuts or inspiring custom bike projects.
"Paul Brothwood's inspirational custom artwork is a worthy winner and we look forward to providing him with his new Harley-Davidson helmet, which will accompany Paul and his HOG chapter to Russia, hopefully in the summer."