The last of the Oregon Trail half dollars came some 14 years after the first were made, marking the longest production period for a single type of United States commemorative coin during the traditional era (1892-1954). The 1939 Oregon Trail halves are also the scarcest, with tiny mintages of just about 3,000 each at the Philadelphia, Denver, and San Francisco Mints. The 1939 Oregon halves were sold in sets of three for $7.50 per set.

Oregon half dollars were designed by husband and wife coin artists James Earle Fraser and Laura Gardin Fraser. The Oregon half dollar is considered one of the most beautiful United States commemorative designs, honoring the pioneers who charted the 2,000-mile path across the western United States during the early 19th century. The obverse features a majestic portrait of a Native American standing before an outline of the United States, which shows a little line of covered wagons cutting across the map where the Oregon Trail was blazed. On the reverse of the coin is a serene scene of a cattle-drive stagecoach approaching the setting sun.

Most of the available 1939 Oregon half dollars are known in Gem condition, ranging from about MS64-66. MS67s are scarce and pieces grading MS68 or higher are extremely rare. Luster on the 1939 Oregon half dollars is generally satiny.