I couldn’t take my eyes off that Cadillac. Built in 1941, it was older than I, original in every respect and probably in better shape. The factory paint looked good and its massive V-8 purred in the morning drizzle.

“There are mechanical concerns…always…you never really know,” its owner, Hank Mulvilhill, said before we departed his Richardson, Texas, home. Hank first drove the Caddy at age 16 when he took his driver’s test. His father bought the car when Hank was three. After the car sat in storage for a decade, Hank rescued it and drove it home 28 years ago.

It was the last Saturday in August 2008. Hank had invited me to follow him to Farmersville, a tiny hamlet 40 miles northeast of Dallas, for my first Bugtussle Trek. Named for the ghost town of Bugtussle, nestled deep in the piney woods, the Trek—which this year celebrates its 50th anniversary—brings together dozens of classic cars and proud owners.

A back country vintage car rally you probably never heard of...