The Best Small Towns of Illinois

What most people think of when they think of Illinois is Chicago. But aside from The Windy City, the Prairie State is covered by farmland, forests, and hills, dotted by picturesque small towns. Many of these towns are, in fact, postcard perfect images of Main Street U.S.A. Want to see for yourself? Check out these scenic small Illinois towns.


Galena is named after a type of lead ore that was mined in the area, and it’s a must see small town destination rich with history. Civil War general and ultimately president Ulysses S. Grant called Galena home, and Abe Lincoln and Frederick Douglas gave speeches here. Over 800 buildings are on the National Register of Historic Places.


Arcola is a lesser known neighbor to nearby Arthur. The two towns sit in the heart of Amish country. One claim to fame is that the creator of the Raggedy Anne and Andy dolls, Mr. Johnny Gruelle, hails Arcola as his birthplace. Arcola is also the Broomcorn Capital of the World, a title it shows off every fall at the Broomcorn Festival. Speaking of Agriculture, don’t miss The Great Pumpkin Patch, with over 300 varieties of squash and gourds.


The very fertile bottom third of Illinois is often referred to as Little Egypt, and some of the towns therein have Middle Eastern names, like Lebanon, Illinois. Lebanon’s main street is picture perfect, with facades that range from the colonial to the Greek revival to the gothic. Stop by the Mermaid House, an inn operated by a retired sea captain and once visited by Charles Dickens.


The entire downtown area of Woodstock is on the National Register of Historic Places, so it’s full of ample opportunities to enjoy guided and self guided walking tours. The picturesque town square is flanked by the Old McHenry County Courthouse and Woodstock Opera House. Claims to fame include being the typewriter production capital of the world and the place where the movie Groundhog Day was filmed.


Princeton’s Main Street district is very well preserved, and it’s conveniently about 1.5 hours outside of Chicago on an Amtrak stopping point. Just outside of Princeton there are two historic covered bridges that are fun to pass through and also make for great pictures. History lovers won’t want to miss the home of Reverend Lovejoy, which as part of the Underground Railroad.

As you can see, Illinois has some very pretty looking All American Towns. For a slightly different taste of small town travel, one with seaside vibes, check out some of the Best Small Towns in Maine.