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I just finished the book Across America by Motor-Cycle written by R.A.F. Captain C.K. Shepherd in 1922 about his 3-month journey in 1919 from New York to San Fransisco on a 4-cylinder Henderson. I think Shepherd was 24 years old at the time of his trip. The book is filled with fantastic descriptions of the complete lack of roads and markings in the U.S. at that time as well as his bizarre adventures, multiple accidents, and continuous breakdowns along the way. There is a Kindle version for 3 bucks. Also, you can get the eBook for free.
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