Four Days in Southwestern Illinois

Enjoy history, the arts, and outdoor adventure in Downstate Illinois’s Western Region.

Day 1

Start out the day by exploring Granite City’s Art and Design District. It features an interactive 10-person swing, gardens, and exhibitions. When you’re finished, head east to Highland. One of the best baked goods you’ll ever have can be found at Patty Cakes, a small business that was featured on TLC’s “Ultimate Cake Off.” For a nice way to burn off the cupcake calories, head to Highland’s Silver Lake where you can hike nearly five miles-worth of trails and enjoy a climbing wall. Wrap up the night in Lebanon by taking in a performance at the Looking Glass Playhouse, followed by a late dinner and drinks at Cobblestone Eatery and Drinkery on Historic Brick Street.

Giant Swing in the Art & Design District of Granite City, IL

Art & Design Swing in Granite City

Day 2

Begin the day with an easy hike around Silver Creek Preserve in Mascoutah. The one-mile paved loop offers a great walk or run around scenic marshland. A short ten-minute drive west will take you to O’Fallon, where folks can test their wits at Code Rulers Escape Room. There are multiple rooms for people to try to escape a certain situation before time runs out. Enjoy some of the biggest food portions you will ever eat at Lotawata Creek in Fairview Heights, which attracts over half a million hungry diners a year. A short drive south, but still in Fairview Heights, sits Centerfield Park, the perfect venue to wrap up a day. Centerfield Park offers bumper boats, go karts, batting cages, mini-golf and more!

Silver Creek Preserve in Mascoutah, IL

Silver Creek Preserve in Mascoutah (PC: Midwest Nomad Family)

Day 3

There is so much to do in Belleville, you can spend a whole day taking in the sights and sounds of Illinois’ largest city south of Springfield. A unique piece of American history can be found at the September 11th Memorial Walkway of Southern Illinois.

Wall Art Mural in Belleville, IL

Belleville Mural in Belleville (PC: Belleville Mural Project)

Take a walk downtown and snap a picture in front of several vibrant murals, then head to Beast BBQ, home of the seven and a half pound BBQ Nacho challenge!

Amphitheater at the National Shrine of Our Lady of the Snows in Belleville, IL

The National Shrine of Our Lady of the Snows Amphitheatre in Belleville

Spend some time walking around the grounds of The National Shrine of Our Lady of the Snows, with many sacred spaces like Lourdes Grotto and the Millenium Spire. Finish the day by taking in a movie at Skyview Drive In, one of the few remaining drive-in theatres in southern Illinois.

Day 4

Take a trip down the Great River Road and start off at the Cahokia Courthouse. This historic venue was built in 1740 and is the oldest courthouse in the state. Explore the charming village of Maeystown, which is tucked away in Monroe County.

Historic and picturesque Maeystown Bridge in Maeystown, IL

Maeystown Bridge in Monroe County

A trip here is like going back to the 1800’s, as 60 significant buildings still exist from the beginning of the village in 1852. The entire village itself is listed on the National Register of Historic Places. Heading further south to Randolph County, take a walk across Mary’s Covered Bridge. This iconic landmark was built in 1854 and is a very popular spot for photographers. End the trip by taking a scavenger hunt on the Popeye Character Trail in Chester, which features 20 different character statues to find around town!

Historic St. Mary's Covered Bridge in Randolph County, IL

Mary’s River Covered Bridge in Randolph County

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