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Blake Hennessy, 32, an employment consultant from Burr Ridge, Ill., on road tripping this year in a 1989 Land Rover Defender 110, as told to A.J. Baime.

At first, we were planning on driving to a trade show in Arizona. But then we thought, if we’re going that far, why not make it a big trip and cross some things off the bucket list? It was late spring, the beginning of road-trip season. My childhood buddy Rob Bedoe and I cleared 30 days and mapped out 10,000 miles, down to Texas, over to the West Coast, to the Canadian border and back.

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