Visitors Guide
Road Trip Itinerary: Explore The Kaskaskia Cahokia Trail

Road Trip Itinerary: Explore The Kaskaskia Cahokia Trail

Posted on 03/01/2021 by Andy Waterman

After a year of little travel and tourism, our adventure bug is starting to itch, and you’re likely right there with us. Road trips are all the rage right now, and they’re a great way to experience things right in your own backyard that you never knew about. The Kaskaskia Cahokia Trail is one such road trip route through Downstate Illinois that is full of historic monuments and outdoor adventure. We took the liberty of putting together a three-day itinerary full of adventure. So roll your windows down, open that sunroof, turn on the radio, and enjoy that open road to some of our favorite places.

Day 1

Prairie du Rocher

We’ll start off in the Historic French Colonial Village of Prairie du Rocher. Wake up on the right side of the bed at Conner House Bed & Breakfast with a big, beautiful room and a delicious breakfast.

Once you’re awake and raring to go, take a short drive to see the Fort de Chartres State Historic Site. Here you will see a 300 year old fort built during the French colonization of the Illinois Country. You can also visit at certain times of the year to be involved in any one of their events like demonstrations or their popular Rendezvous gatherings (COVID-19 permitting).

After you’ve had your fill of history, it is time to fill your belly. Enjoy some delicious comfort food from Lisa’s Market Street Grill & Bar. Pick from your choices of soup, salad, sandwiches, pizza, wings, and so much more!



A quick six minutes away lies the Village of Modoc, home of the Prehistoric Modoc Rock Shelter National Historic Site. You will bask in the glory of a rock cliff that was uncut by the Ice Age floods. This cliff has been a source of shelter to many for years. You will learn so much about the people who occupied this area from as early as 9,000 years ago.

For lodging, the Kaskaskia River Recreation Area is the perfect place to pitch a tent and camp for the night. Their sites that are equipped with electric, a picnic table, and grill – and you can spend some downtime swimming, fishing, and boating.

By now it’s dinner time, and Boondocks Country Tavern is the best place to eat, drink, and relax after a long day of adventure!

Day 2

Ellis Grove

Another day, another destination! After packing up your campsite, a short nine-minute drive will lead you to Ellis Grove. The first stop is at is the Fort Kaskaskia State Historic Site and Garrison Hill Cemetery where the French defended Kaskaskia in the 1700s. Fort Kaskaskia boasts arguably the most beautiful view of the entire trip – a scenic overlook of the confluence of the Mississippi and Kaskaskia Rivers. This view is especially beautiful in the fall!

The second historical site is the Pierre Menard Home; Menard was a businessman who also served as the state’s lieutenant governor. This 1815 home gives a great look and insight on French Creole-style architecture. The home is a great place to feel like you have stepped into a new era!



After a full morning of learning about southern Illinois history, it is time for some grub, and Chester has plenty of delicious restaurants to choose from. Grab some comfort food like fried chicken, chicken and dumplings, and some cheesecake for a little midday delight at Reids’ Harvest House. If salads, sandwiches, pasta, and pizza are more your speed – then make a trip to Joe’s Pizza. St. Nicholas Landmark is also a fantastic option for those looking to enjoy a tasty craft beer with their meal!

You likely saw the signs as you pulled into town, but it’s worthy to note that Chester’s claim to fame is Popeye the Sailor Man! Everywhere you look there are signs, murals and picture cutouts celebrating everyone’s favorite sailor! Take a walk on the Popeye Character Trail and try to find over a dozen different characters from the Popeye cartoons scattered around town. Of course, you will have to get a Popeye souvenir as well – so stop on by Spinach Can Collectibles and pick something out!  

Once you’ve had your Popeye experience enjoy some south of the boarder flavors at Tequila Mexican Cantina. And if it is an adult only trip, Benson’s Wine Bar would be the place to go with top-tier alcohol, and live music – you can also bring your own snacks!  

When it is time to settle down, unwind at Best Western Chester Hotel. With comfy beds, extensive cleaning, an outdoor pool, and a continental breakfast, you will surely rest easy and wake up refreshed.      


Day 3


Did you know that a portion of Illinois extends WEST of the Mississippi River? It's true! You actually have to cross into Missouri to enter the Village of Kaskaskia – home of the famed ‘Liberty Bell of the West’. France’s King Louis XV gifted this bell to the Catholic Church of New France – today it sits inside the Immaculate Conception Catholic Church in Kaskaskia!

After snapping a few photos of the famed bell, go exploring at the Kaskaskia River State Fish and Wildlife Area. There are opportunities for fishing, boating, hunting, and hiking at this amazing outdoor area! If you brought some lunch, it’s definitely a great place to relax with a nice picnic to finish the trip off.

There are so many great places to visit and explore in Downstate Illinois and this is a guide to get you started. Go out and make your own adventure and we hope to see you soon! For more information on our region of southern Illinois – visit



NASCAR Race Weekend Trip Itinerary

Coming this summer, the Worldwide Technology Raceway is hosting the Enjoy Illinois 300 Worldwide Tec...more!

Cahokia Mounds Update - February 2023

The Cahokia Mounds State Historic Site is an iconic attraction that serves as a tourism hotspot for ...more!

A Scenic Road Trip for Biking & Balloons in Downst

There’s a little pocket of Illinois paradise you probably haven’t slotted into your Midw...more!

Road Trip Itinerary: Take a Drive on IL Route 1

Here is a fun fact, the longest State Route in Illinois runs through our region! Illinois Route 1 is...more!

FREE Visitors Guide!
Request Your FREE
         Downstate Illinois
     Visitors Guide
        View Online Request Today!