We found a railway intruding at Chester, Illinois; Chester has also a penitentiary now, and is otherwise marching on. At Grand Tower, too, there was a railway; and another at Cape Girardeau. The former town gets its name from a huge, squat pillar of rock, which stands up out of the water on the Missouri side of the river—a piece of nature's fanciful handiwork—and is one of the most picturesque features of the scenery of that region. For nearer or remoter neighbors, the Tower has the Devil's Bake Oven—so called, perhaps, because it does not powerfully resemble anybody else's bake oven; and the Devil's Tea Table—this latter a great smooth-surfaced mass of rock, with diminishing wine-glass stem, perched some fifty or sixty feet above the river, beside a beflowered and garlanded precipice, and sufficiently like a tea-table to answer for anybody, Devil or Christian. Away down the river we have the Devil's Elbow and the Devil's Race-course, and lots of other property of his which I cannot now call to mind.
From the Mythic Mississippi Project
Chester is at the entrance to the region where Illinois began — mere miles from the confluence of the Kaskaskia River with the Mississippi, from the French Fort Kaskaskia and the recently discovered (by Dr. Mark Wagner, SIU) American Fort Kaskaskia, from Prairie du Rocher and Fort de Chartres, and where the old village of Kaskaskia used to be located before the great flood of 1881 turned it into an island. The Pierre Menard house is nearby as is Garrison Hill Cemetery, where the graves of Kaskaskia were relocated when the land was inundated.
Mark Twain spent a significant amount of time in the Illinois Chester between 1857 and the start of the Civil War. It is known that he stayed in the Cliff House and in his book, Life on the Mississippi, Twain recalls the Cohen House’s blue windows, which he could see from the river.
Chester has an exceptional piece of WPA (Works Progress Administration) art in its post office, which should contribute to a National Register of Historic Places designation. In the post office you can see “Loading the Packet”, painted by Fay E. Davis in 1940. This historically retrospective painting shows African Americans carrying heavy white sack bags of mail to the waiting steam boat docked in the Mississippi River. Transcending the beauty the painting itself, the artwork can be read as an ethnographic text as much as a historical remembrance. [4]