Samuel Smith is said to be the town's founder because he built the first home in Chester, established a ferry system, and began the construction of a mill in 1829.

[5] The first business in Chester was a general store that opened in 1830 along with a castor oil press established by R. B. Servant, who furnished farmers with seed and growing methods to later buy the beans they produced for oil extraction.

Content Walker, the bride and Amzi Andrews, the groom held their wedding in a 16 feet square log cabin.

It started out as a small sawmill with a corn-grinding attachment which encouraged the townspeople to plant grains, and in a short time the first Cole flour mill was built.

Nathan Cole also brought the first electric generator to Chester and used the surplus of power from the mill to operate street lights.

In 1922, a second building was built, and the company had more than 1000 employees and was producing thousands of pairs of children's shoes.

During World War Two, the factory operated primarily by women produced military/combat boots for the troops in service.

The mill grew to employ more than 275 people and produced over 300,000 pairs of stockings a month with annual payroll exceeding $700,000.

It was completed in 1941, although due to the delivery of the filtration system being delayed it did not officially open until May 30, 1942, under the management of William Weber.

Due to leaks and other deterioration issues, as well as high repair costs, the pool has been closed since 2014.

Chester's big event is its annual Popeye Picnic and parade, held the weekend after Labor Day.

Popeye fans travel from all over the United States and the world to partake in the weekend activities.

[9] Popeye's Picnic is an event held in Chester the Friday, Saturday and Sunday following Labor Day in the month of September.

The parade consists of local school bands, band fronts, such as dance teams and cheerleaders, floats from various businesses, fire departments, veterans representing the United States, politicians marching, clowns passing out stickers and candy, and finally horses trail the parade.

On April 11, 1842, Charles Dickens, the author of A Christmas Carol and Great Expectations, visited Chester with his wife.

[14] Mark Twain, the author of The Adventures of Tom Sawyer, a pilot on the Mississippi River between 1857 and the Civil War, supposedly on many of his trips stayed at Chester's Cliff House, a fine river hostelry.

[14] The Chester post office contains a federally commissioned mural, Loading the Packet, painted by Fay E. Davis through the Section of Painting and Sculpture, later called the Section of Fine Arts, of the Treasury Department.