Illinois' Laidback City On The Mississippi River Is A Scenic Day Trip From St. Louis With Historic Charm

The state of Illinois, known by many monikers including "The Heart of America," is more than a crossroads between the eastern and western U.S.  About 65 miles south of St.Louis, along the banks of the storied Mississippi, lies Randolph County, a region that earned the motto "Where Illinois Began". Its seat is the city of Chester, founded in the early 19th century, and a witness to prehistoric hunters, French explorers, the Revolutionary War, and the famous Popeye. For those in St. Louis, experiencing Chester's quaint charm and deep history is just a scenic day trip away. 

Chester is a small city with a population verging on 7,000 residents. Although it was founded primarily as a trading center and ferry town, human life in the area dates back to around 8,000 B.C., as evidenced by ancient artifacts found at the neighboring Modoc Rock Shelter. The city is rich with sites to explore, such as a beautifully preserved covered bridge, the Popeye Museum, and St. Nicholas Landmark, a commercial building built in 1830 that currently houses a trendy brewery. 

To visit Chester from St. Louis, drive down the Illinois Route 3 and you'll reach the city in just under 90 minutes. You can meander through the laidback streets while on the lookout for numerous statues of "Popeye" characters scattered throughout, an homage to the cartoon's creator and Chester native Elzie (E.C.) Segar. Take in views of the Historic Chester Iron Bridge and the mighty Mississippi below, or check out the Cohen Memorial Home, which is said to have left an impression on Mark Twain during his steamboat travels in and around Chester.

Outside the Randolph County Courthouse in Chester, fly five distinct flags that represent the political history of the city and its surrounding region. Mounted beside the Stars and Stripes are a French fleur-de-lys, the English Union Jack, and flags for Illinois and Virginia. Chester was once considered a gateway to the French Colonial Illinois, and sits a few miles downstream from Kaskaskia, the former state capital and currently an eerie "American Atlantis". It also borders a marker on the Lewis & Clark National Historic Trail, where the expedition party once camped on nearby Horse Island.

Chester was formerly known as Smith's Landing, after Samuel Smith, who built the first house there in 1829, yet it was his wife who prompted the name-change to Chester, after her English hometown. The city grew into a relevant riverside trading center, known for its flour mill and castor oil production. Saint Nicholas Landmark, located at 111 Ferry Street, has seen much of the city's commercial history pass through its doors. It is now a local spot for tasty bites and beers courtesy of St. Nicholas Brewing Company.

When you arrive in Chester, it's best to park near the Chester Welcome Center, a central location within Segar Memorial Park that will allow you to explore the city with ease. The park has expansive views of the Historic Chester Iron Bridge and the Mississippi River. Heading further into town, you can visit the "Stone Cottage", a landmark listed on the National Register of Historic Places. The one-story limestone home, built in the German style, offers a glimpse of how working people lived in the mid to late 1800s.

 Mark Twain's renowned memoir "Life on the Mississippi" immortalized the romantic era of steamboats long before the Mississippi River was named as the "most endangered" due to habitual flooding. The book gives a shoutout to Chester and its riverside railroad tracks, known as the Chester Subdivision. Legend has it that the great author dubbed the Cohen Home in Chester "the house with the blue windows". The Victorian-style house was built in 1855 and is located at 523 Harrison Street. It was acquired by the Cohen family in the 1880s.

As you explore Chester, you will quickly understand that its citizens are proud of anything to do with Popeye the Sailor Man. You will certainly stumble onto the Popeye Character Trail, a series of 19 granite statues of the beloved cartoon characters that can be found around town. Growing up in Chester, Elzie Segar based his famous characters on the unique personalities he encountered, and the city keeps the fanbase engaged with the Popeye Museum located on 1001 State Street.

On the drive back to St.Louis, consider taking a six-minute detour to see Mary's River Covered Bridge. The quaint structure was built in 1854 and is possibly the oldest covered bridge in the state, with most of its original white oak planks still intact. Should you decide to take your adventure further downstream, Missouri's Cape Girardeau, a charming city getaway and home to hundreds of restaurants, is an hour's drive away from Chester.