In 1811 John Jacob Astor, the wealthiest man in America, orchestrated one of the most significant explorations of new lands in the West. Astor, America's first multi-millionaire and a successful fur trader and entrepreneur, arranged for two groups of men to travel from St. Louis to the West in hopes of expanding his successful fur trading business westward.

One of the groups he sent on this journey ran out of food, supplies and livestock due in part to the tough terrain they encountered. A small group was sent back to St. Louis to request assistance from Astor. This group, led by Robert Stuart, stumbled upon a large passage through the Rocky Mountains. This passage permitted sizeable wagons to pass through it, something that was previously believed to be practically impossible.

As a result, this exploration gave way to the historical and significant path to the West, allowing passage for well over a half-million settlers. Most of the settlers who traveled this 2,000 mile path consisted of women and children, as can be seen on the obverse of the Oregon Trail Commemorative coins. These families were in search of a better life in the West, where it was believed there were new lands with bountiful harvest. Several years later, many more families would travel further west, hoping to prosper from the California Gold Rush.

The Oregon Trail Commemorative coins were produced for several years with the same design, with the exception of the different dates and mint marks. The different coins were produced as follows:

They were first produced in 1926 at the Philadelphia and Denver Mints.
No coins were produced in 1927, as1926-dated coins remained in the Mint's inventory.
In 1928, the coins were only produced in Philadelphia.
In 1933 and 1934, they were only produced in Denver.
In 1936, the coins were produced in Philadelphia and San Francisco.
In 1937, they were only produced in Denver.
In 1938, the Mint produced the coins in Philadelphia, Denver and San Francisco.
In 1939 the Mint produced the coins in Philadelphia, Denver and San Francisco. (The 1939 coins contain the lowest mintages for the Oregon Trail Commemorative series, as each mint produced and sold 3,000 coins).

The Oregon Trail Commemorative coins were introduced to commemorate all of the brave women, children and men who took this extremely difficult journey. These brave individuals set a significant path which helped enable the expansion of America further to the west.

The Oregon Trail Commemorative coins display a Conestoga wagon on the obverse. On the wagon, there are a woman and child (more than likely a mother and her child). Walking and leading the crew is probably the father of the family who is guiding the oxen through the Oregon Trail in a quest to what they hope will be prosperous new lands. Portrayed in the background is a radiant, illuminating sun with large rays extending toward the rim of the coin. Arched above this historically significant scene are the words “In God We Trust.” The theme celebrates the hundreds of thousands of individuals who were brave enough to take this extremely difficult journey.

An American Indian with an envious and powerful physique is featured on the reverse. The Indian seems to be posed in a serious stance, either to stop some of the settlers or briefly interact with them as they pass through the Indian-inhabited lands. In his right hand, he unthreateningly carries his hunting bow. On his left shoulder he carries a long, draped blanket. He is wearing a long, feather-ornamented bonnet. Behind him is an outlined map of the United States of America, and within the map there several Conestoga wagons traveling to the new lands in the West.