Mile 109.9 - Chester Bridge

John Ruskey

20 Apr 2026 � 1 min read

109.9 Chester Bridge

The shiny steel Chester Bridge glistens in the sunlight as you come around Beaver and Kaskaskia Islands from upstream. It is advantageously placed in a natural narrows where the Missouri bottomland comes close to the Pawnee Hills at Chester. It is the first highway crossing below Jefferson Barracks in St. Louis, 60 miles upstream. The next crossing found downstream is in Cape Girardeau. Tragedy struck the bridge on a stormy night in July, 1944 when a windstorm of tornadic force caused two 670-foot spans to collapse into the river. Reconstruction took two years and on August 24, 1946, the bridge was reopened to traffic. This became Chester’s second toll bridge for many years. It is still the only bridge between St. Louis and Cape Girardeau, Missouri.

Chester is the home town of Elzie Crisler Segar, the cartoonist who created ‘Popeye The Sailor Man’. There is a small park on the Illinois side of the crossing to remember Segar, which includes a life-sized statue of Popeye. The city celebrates Segar in the annual Popeye Festival held each labor day weekend.

The village of Kaskaskia is located on the west side of the Mississippi River just upriver of Chester. Kaskaskia was a commercial and transportation hub in the 1800s. In fact, it was the first capital of Illinois until 1820. The Mississippi River shifted course to the east side of Kaskaskia in the middle and late 1800s. As a result, the village is now located on the west side of the Mississippi River. But since the state line follows the historic path of the Mississippi River, Kaskaskia remains a part of the state of Illinois. The fortunes of Kaskaskia started to wane following the shifting of the river. Its population steadily declined throughout the 1900s with only 9 people remaining in 2000. (From the City of Chester Illinois and the John Weeks websites).

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