Cruising across America in a 1959 Ford Thunderbird

  • To get to the West Coast, Stephen Webster drove south from New York, through Tennessee, then picked up Route 66 in Texas.
  • Shaun Tolson

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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 before you realize that this is something that almost everyone wants to do at some point during their lives. It’s everything that America and the road have to offer. I’ve seen more of this country than most Americans have. On the outskirts of Amarillo, for example, we came across the world’s largest cross and the world’s largest 72-ounce steak dinner, both of which were guaranteed to produce some kind of religious experience.

“The road trip is a very romantic ideal, and in a 1959 Ford Thunderbird the effect is even greater. When you’re driving on the freeway in a ’59 Thunderbird—your foot firmly planted on the pedal inscribed with the word power—you feel like Charles Lindbergh flying across the Atlantic. And because the car is 17 feet long, you don’t so much steer it as shepherd it between lanes. 

“We chose not to take Route 66 from Chicago. Instead, we headed south through Nashville and Memphis before eventually connecting with Route 66 in Texas. As we were entering Nashville, the car seized up. With an old car you can’t expect everything to be the way it should be; it has a personality that you have to deal with. We managed to crawl our way to a garage, one that specialized in classic British sports cars. The owner spent most of his day working on our ’Bird, and not only did he fix it, he refused to charge us. ‘I just want to see you guys make it,’ he said. ‘Let me know when you do.’ It was experiences like that that captured the spirit of the trip. You drive through tiny, forgotten towns and big cities, and you meet people in both places who wish you well. 

“After 3,500 miles and 52 liters of oil, we arrived at the Pacific. That road trip was my first time-out since I had gone into business for myself. Since then, I’ve taken one big road trip every year. Once you’ve done it, you realize how important a time-out like that can be. If you give yourself the opportunity to take such a trip, you’ll never regret it.”

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