At 10 a.m. on September 3, 1911, Dr. S. R. M. Kennedy, Frank L. Mayes, A. M. Avery, Jr., and F. C. Brent, Jr., left Pensacola for Chicago in Kennedy's Speedwell 50 touring car. Calling themselves the "Gulf-to-Great-Lakes-As-The-Crow-Flies" pathfinders, their ostensible mission was to represent Florida at the Fourth International Good Roads Congress. But their real goals were to add a Pensacola-to-Birmingham route description to the American Automobile Association's Blue Book (to complete the trail between the Great Lakes and the Gulf) and to promote Pensacola as a destination for midwestern tourists. At a time when road conditions rattled bones and nerves, required chains during rainstorms, and even portended death along mountainous trails, they completed their 1149-mile trip on September 12 in a total running time of 76 hours.

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