Texas Highways Magazine

Cowboys in Cuba

Beneath a warm Caribbean sun, down a twisted road from the tattered colonial city Santiago de Cuba, an American soldier stands frozen in time.

It’s a statue, actually, in a small park that commemorates the derring-do of Teddy Roosevelt and his Rough Riders, formally known as the 1st U.S. Volunteer Cavalry, who helped drive Spain out of Cuba during the Spanish-American War in 1898.

Roosevelt has long been one of my favorite politicians of any era, thanks to his conservation initiatives, but I knew little about his Texas connections. Then my friend Wayne Fairchild, a professional adventure outfitter in Montana, invited me to join him on a 10-day tour of Cuba. An Army veteran, Fairchild

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