Steve DeCosa, 67, a retired high-school teacher from Oswego, N.Y., on his Harley-Davidson s, as told to A.J. Baime.

I had never ridden a motorcycle at the time I retired. Shortly after leaving teaching in 2011, I bought a late-model Harley-Davidson. I passed my road test on a Thursday, and by Saturday, my wife Joan and I were on a 2,500-mile ride.

The following year I saw the send-off of the 2012 Motorcycle Cannonball, a coast-to-coast ride for antique bikes. I thought, I need to be a part of this. Joan and I bought a 1927 Harley JD and began a restoration, with a hard deadline—the 2014 Cannonball.

In our two-car garage, we did our own painting, pinstriping and nickel-plating. We did the mechanical assembly ourselves, too. Anything we did not know how to do, we learned from YouTube videos. (I joke that we’re graduates of YouTube University.)

With Joan as my crew chief, we made the ride successfully from Daytona Beach, Fla., to Tacoma, Wash. But the experience made us long for more. So we pieced together a 1915 Harley 11F from parts we bought from all over the country, with a goal to finish in time for the 2016 Motorcycle Cannonball.