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Sixteen years ago, the British jeweler STEPHEN WEBSTER bought an all-original 1959 Ford Thunderbird for $5,000. Three years later he enlisted the help of his friend Jeff Feero to restore it. When the car was finished in 2007, Webster and Feero celebrated by taking it on a 10-day road trip from New York City to Santa Monica, Calif.

“The significance of a cross-country road trip hits you almost immediately. You don’t have to go very far beyond the first gas station bef…