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Find Your Adventure in Illinois South!

From Local Experts

3 Days 192 Miles


Belleville, Carlyle, Casey, Chester, Columbia, Greenville, Madison, Nashville, O'Fallon, Vandalia, Waterloo

from the local experts at Discover Downstate Illinois

Discover Downstate Illinois consists of 22 counties worth of so much to see and do!

From countless outdoor adventures, to unforgettable experiences with our Illinois Made businesses – Discover Downstate Illinois is prime for a weekend road trip!

Day 1:

Chester, Waterloo, Columbia, Belleville, Madison, O’Fallon

  • A kid walking through a sunflower field

Start off the day in Chester, home of Popeye the Sailor Man! Chester is the hometown of Popeye’s creator, E.C. Segar – and the community celebrates their favorite sailor man every day. You’ll find murals, the Spinach Can Collectibles souvenir shop, and a Popeye Character trail – which consists of 15 statues of Popeye characters that are scattered around town for visitors to find! 

A scenic drive north on the Great River Road will lead you to Waterloo and Columbia in Monroe County. There you’ll find plenty of food and drink; but two of the best places to get a great beverage are Stubborn German Brewing in Waterloo and Stumpy’s Spirits and Distillery in Columbia. Stumpy’s is an Illinois Made business that offers tours as well as a wide array of whiskey and vodka.

Not far north of Monroe County lies Eckert’s Country Store and Farms in Belleville. Visitors can pick their own fruit like apples and peaches, or take a walk through their market which offers up some amazing fresh foods and baked goods. If you're hungry, Eckert's also has a restaurant with some amazing homestyle lunch and dinner options. 

Another drive north on the Great River Road will lead you to the iconic Old Chain of Rocks Bridge in Madison County. The Old Chain of Rocks Bridge is a huge piece of Route 66 history in the region, and a fantastic opportunity to snap some amazing photos from one of the longest pedestrian bridges in the country. 

You can wrap the day up by heading back south on the Great River Road to World Wide Technology Raceway. There they have the Gateway Kartplex, which is an 11-turn half-mile track with karts that can go up to 55 miles an hour! 

By now you’re likely wiped, so take a short drive east on Interstate 64 to O’Fallon and stay in one of their many hotels!

Stay at Candlewood Suites.

Day 2:

Nashville, Carlyle, Greenville

A quick drive from O’Fallon to Nashville will lead you to Rainbow Ranch Petting Zoo, a family favorite! At Rainbow Ranch you can pet zebras, camels, kangaroos and more. If you’re feeling up to it, they’ll also let you bottle feed some of the baby goats and calves.

Not far north of Nashville on Route 127 sits Carlyle Lake, the largest man-made lake in the state. There are opportunities to camp, fish, hike, bike, sail, paddleboard and more. Families love to take advantage of the beach at Carlyle Lake and build sand castles while watching sailboats in the distance. If camping isn’t your style at the end of the day, rent one of dozens of cottages right near the lake.

Unwind at Bretz Wildlife Lodge & Winery before checking in to Hazlet Cottages on Carlyle Lake.

Day 3:

Vandalia, Casey, Martinsville

  • Worlds Largest Rocking Chair

History is huge in ILLINOISouth, and one of the most historic places is the Old State House in Vandalia – the oldest remaining Illinois State Capitol. Take a look inside, where you’ll find the very place that Abraham Lincoln began his political career. Not far from the State House is the National Road Interpretive Center, where you can learn all about the National Road which was a key factor to westward expansion. 

Next, head east on Interstate 70 and prepare to be amazed. Stop for lunch at the Moonshine Store in rural Clark County. The doors open at six in the morning here, and there will be a line out the door not long after. These are some of the best cheeseburgers you’ll ever have, but you need to get there by 12:30 p.m. before they turn the grill off! 

From there, you can wrap up with Casey - home to Big Things in a Small Town. There are a dozen of the World’s Largest objects in Casey, along with several other HUGE attractions. Take a picture inside the World’s Largest Mailbox, or ring the World’s Largest Wind Chime! Children will also love to stop inside the Casey Candy Depot for a wide array of sweet treats, and inside you’ll find the World’s Largest Wooden Shoes.

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