Mississippi River Road Trip – Illinois & Missouri

My friends and I set out on a drive to see some sights In Southern Illinois and Missouri. In general, we followed along the Mississippi River. We headed south towards Chester, Illinois. While driving along Route 150, about 10 minutes outside of Chester, there is a sign for a historical marker. Just off the road sits Mary’s River Covered Bridge. Little Mary's Covered Bridge (2)

The bridge spans Little Marys River and is 86 feet long. A local man built a toll road between the port town of Chester and Bremen in order to move goods inland. Construction began in 1854.

Little Mary's Covered Bridge (1)

The bridge was in service until 1930 when it closed to only foot traffic. The Mary’s River Covered Bridge is the last remaining covered bridge in Illinois.

Little Mary's Covered Bridge (3) Little Mary's Covered Bridge (5)

Little Mary's Covered Bridge (4)

After visiting the bridge, we drove into Chester, Illinois. Chester is home of Popeye! Just off Route 3, before you cross the Mississippi River into Missouri, is the famous Popeye statue. This is another one of those places that if you are from Illinois, you have to say you have been there,

Popeye (2)

Chester is known as the home of Popeye the Sailor Man because the creator was from Chester and it is believed that many of the characters were based on local people.

Popeye (1)At the far end of the small park, there is an observation platform. From here, you get an expansive view of the Mighty Mississippi River and of the Chester Bridge.

ChesterJust before the statue, there was a sign for a scenic overlook. We headed up the bluffs and just behind the Randolph County Courthouse is a small overlook.

Chester 1

Just down the road a bit, we found the Chester City Steps. It is a bit of a unique landmark so we figured why not check it out.

Chester  (2)When Chester was first founded in 1829, most of the town was below the bluff, along the riverfront. As the city began to expand to on top of the bluff, the city steps linked the the two together.

Chester  (1) Chester  (3)Once we got down to the riverfront, we got a up close view of the river and then a train came rolling by!

Chester Train

From here we headed to Inspiration Point. This is a hike that I have had on my “To Do” list forever now. After crossing the Big Muddy River, you turning on Muddy Levee Road. We once again, saw another train!

Inspiation Point (5)Once you round the bend in the road, the towering bluffs come into view. The are stunning.

Inspiation Point (1)Inspiation Point (2)Inspiation Point (4)Mother Nature had different plans for us though. Due to one of the wettest June’s in history, we are experiencing major flooding in the area. The Big Muddy River was well over its’ banks and the road to the trailhead was closed.

Inspiation Point (3)

So stay tuned for this hike. Hopefully we will be able to complete it once the rain stops and the flooding subsides.

From here, we drove south and crossed the Mississippi River at Cape Girardeau. We stopped at the Cape Girardeau County Park, just off Interstate 55 and found the Maple Hollow trail.Maple Hollow (1)This was a great trail. It is just a mile long, paved and through a beautiful forest.

Maple Hollow (4) Maple Hollow (3) Maple Hollow (2)

Our final stop on our road trip was the Bollinger Mill State Historic Site. Stay tuned for that post!

Thanks for stopping by! If you have any questions or comments, please leave them below!

Categories: Cape Girardeau, Chester, RandomnessTags: , , , , , , , , , , , ,


  1. Love love love the covered bridge!!

    Liked by 1 person

  2. I have never heard of that covered bridge. I need to take that trip again to Popeye area and find those bluffs. Oh, and welcome to Cape!


  3. There are several authentic covered bridges in Illinois:
    –west of Rockford
    –2 south of Princeton
    –in Crestwood
    –south of Oquawka
    –south of Springfield
    –east of Cowden
    –east of Knoxville
    –west of Greenup
    –entrance to Lake of the Woods State Park
    Source: website coveredbridgemap
    Another great resource website dalejtravis

    Liked by 1 person

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