The Saga of Windwagon Smith (1961)

Sea Captain Windwagon Smith hits Westport, Kansas, the starting point of the old Oregon and Santa Fe Trails, and is quickly the laughing stock of the town; instead of traveling in the usual oxen-drawn covered wagon, he is at the helm and wheel of a Contestoga-type wagon with a full set of sails. He plans to go to Oregon by taking advantage of the prairie winds. First, he wins over the town mayor, falls in love with the mayor's beautiful daughter, Molly Crum, and then secures financial backing from the townspeople. He sets sail across the plains, with Molly Crum as a covered-wagon stowaway, and a Kansas twister looming on the horizon. And, then, the wind hits the sails. And the fan, too, if he had had one.

Unfortunately the movie The Saga of Windwagon Smith is not yet available on HBO Max.