When The Great American Race rolled through Texarkana during its cross-country trek in 2002, the rumble and cool appearance of automotive classics appealed to the kid in 62-year-old Texarkana, Texas, resident Alex Tipton. “When they came through, I looked at those people in those beautiful old cars and thought, ‘Man, one of these days I’m going to do that,’” said Tipton, now 67. “But I also knew you had to have the time and money.” Tipton and his brother, Arthur, talked about how they might become participants in the race for the next two years. Arthur...

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