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Steve DeCosa, 67, a retired high-school teacher from Oswego, N.Y., on his Harley-Davidsons, 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…