Depicts a covered Conestoga wagon drawn by two oxen moving west, towards the setting sun. The inscription “In God We Trust” appears above with “Oregon Trail Memorial” and the date below. The designers’ initials appear behind the wagon; five stars appear below the vehicle.

Officially, the US Mint states this as the obverse of the coin, although the designers of the coin and many collectors consider this the reverse of the coin.

The Conestoga wagon is a heavy covered wagon that was used extensively during the late eighteenth century, and the nineteenth century, in the eastern United States and Canada. The term Conestoga wagon refers specifically to this type of vehicle; it is not a generic term for "covered wagon". It was named after the Conestoga River or Conestoga Township in Lancaster County, Pennsylvania, and thought to have been introduced by Mennonite German settlers.

Engraver: James Earle Fraser

Depicts a Native American, standing erect with outstretched arm in a gesture of peace. The Native American wears a headdress, has a blanket and bow, and is superimposed on a map of the United States, with a line of Conestoga wagons heading west. The design is carried to the rim of the coin; Hudson Bay is visible in the upper right.

The Frasers' design for the half dollar has been widely admired. Numismatic historian Don Taxay called the coin "the most beautiful as well as the most truly 'American' U.S. coin. It testifies to the fact that authentic genius, even when trammeled by the necessities of a modern, mechanical mint, can transform our coinage into a work of art."

Engraver: Laura Gardin Fraser