Before the Great Northern Railroad came through, ranchers had to drive their cattle all the way to Minot, North Dakota to market. This was a favorite resting spot of theirs on the way east.
The town was named by the first telegraph operator thereafter his hometown in Pennsylvania. Of all the homestead communities between Havre and Shelby, Chester was the shining star. It beat Joplin in an election for the designation of the county seat for Liberty County in 1919. Much of its early growth was attributed to the efforts of two men—Brown B. Weldy and Charles Baker.
Weldy owned a ramshackle hostelry called the Prairie Inn. At a time when homesteaders were living in tents for temporary shelter, the Prairie Inn was filled to overflowing. Weldy was a man of many talents. He was a land locator, postmaster, merchant, justice of the peace, and newspaper editor. His biggest talent was as a booster for the town. As one historian noted, “Weldy seemed to be the sort of person that made you think you heard an enthusiastic brass band in the background when he spoke and the urge to fall into step was overwhelming.”
Another landmark building in the early days of Chester was the Chester Trading Company. It was well established in 1908 when Charles F. Baker and his partner Alex Wright purchased it. Baker started out as a traveling merchant carrying his clothing and wares in covered wagons to the ranches along the Canadian border. Baker’s store sported a sign that claimed: “We Sell Everything.” If there was a buyer for it, they sold it. Baker and Wright often granted customers credit that ran for years. His pride and joy were his tiled meat case. When asked why he entered his store unarmed to chase away a burglar he answered: “We mighta got shootin’ back and forth and hit my meat case.”