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Stop At These 8 Charming Small Towns In Illinois

While Illinois is largely known for its big cities and connection to Abraham Lincoln, the state is full of small towns worth exploring. From storied towns with picturesque vistas to rural communities who have embraced the wacky and weird to attract visitors, there’s a little bit of everything in Illinois. Whether you head west toward the Mississippi River or to the state’s southernmost tip, Illinois has all sorts of historical, culinary and cultural adventures in store for you. 

The next time you’re planning a Midwest road trip, consider one of these small towns in Illinois. 

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Casey, Illinois

World's largest pencil in Casey, Illinois
Photo courtesy Illinois Office of Tourism

If you’re searching for a small town with big things to see (literally) look no further than Casey. Located in the southern part of the state, this town of about 2,600 people has fully embraced giant attractions to draw travelers off the interstate and into their community.

Beginning in 2011, the town installed the World’s Largest Wind Chime and its aspirations have only grown from there. Today, Casey has 12 attractions with “world’s largest” designations as well as a lot of other fun big things to explore. 

Where to stay: Eighteen-Ninety is the highest-rated hotel in Casey. Read TripAdvisor reviews.

Galena, Illinois

Bottles at Blaum Bros. Distillery in Galena, Illinois
Photo courtesy Illinois Office of Tourism

Located on the bluffs of the Mississippi River, Galena is a cozy, historic town that’s perfect for a getaway no matter the season. Start your adventure with a stroll along downtown Galena’s Main Street. This bustling business district has more than 100 independently owned shops and boutiques as well as a wide variety of restaurants. Breakfast at The Goldmoor Inn is among the best in the Midwest!

If you want to sip on something local, you won’t want to miss Galena Brewing Co. and Blaum Bros. Distillery. Take in some local historic with a tour at the Ulysses S. Grant home and, if you visit during the winter, hit the slopes at Chestnut Mountain Resort. 

Traveling with kids and wants to do something more active in Galena? You can also go horseback riding and hand-feed animals (like mini pigs) or canoe at Riverview Ranch & Resort.

Where to stay: Irish Cottage Inn & Suites and Aldrich Guest House are the two competing favorite places to stay in Galena. Read TripAdvisor reviews for Irish Cottage Inn & Suites and Aldrich Guest House.

Nauvoo, Illinois

Two girls and a statue in Nauvoo, Illinois
Photo courtesy Illinois Office of Tourism

If you’re a local history buff, Nauvoo just might be for you. This small community has a big connection to the history of Mormonism with Joseph Smith and other founding members of the church calling the area home in the 1840s. Much of the historic town has been preserved and during the tourist season you can even spot reenactors around the local, historic businesses.

Given the area’s Mormon history, you’ll also find Joseph Smith Historic Site, Brigham Young Home, Smith Family Cemetery and more in town as well as the modern LDS Nauvoo Temple. 

Where to stay: There are quiet a few historic buildings-turned-inns Nauvoo. Among the more interesting options are the Nauvoo Log Cabins. Read TripAdvisor reviews for Nauvoo Log Cabins.

Arthur & Arcola, Illinois

A mural in Arcola, Illinois
Photo courtesy Illinois Office of Tourism

Enjoy an Amish adventure in the neighboring communities of Arthur and Arcola. Here you’ll find hearty food with baked goods and locally-made cheeses galore with the occasional horse and buggy sharing the rural roads.

Though Arcola has another claim to fame as the home of the Raggedy Ann doll, which was invented in this part of Illinois in the early 1900s. Today, the community celebrates with an annual Raggedy Ann Festival. Arthur has its fair share of festivals too. Most notable is the annual Arthur Cheese Festival, which is held each Labor Day weekend and draws tens of thousands to the small downtown to celebrate. 

Where to stay: There aren’t a lot of accommodation options in Amish country, but one of the highest rated inns in Arthur to consider is Arthur’s Country Inn. Read TripAdvisor reviews of Arthur’s Country Inn.

Woodstock, Illinois

A cafe in Woodstock, where the film
Photo courtesy Silly America via Flickr

Quite possibly Woodstock’s biggest claim to fame is as the filming location of the cult classic film “Groundhog Dog” with Bill Murray. As the film’s popularity grew, the town embraced the offbeat holiday and now holds an annual festival to celebrate the town where it’s always Groundhog Day. In fact, Woodstock even has their own groundhog named Woodstock Willie.

Outside of rodent-focused holidays, Woodstock is a fun place to visit year-round. With a historic square and ample locally owned shops, there is no shortage of small town charm in Woodstock. 

Where to stay: Fans of the movie “Groundhog Day” are going to want to stay at the inn from the movie. Book a room at Royal Victorian Manor for that opportunity – you can even book the room Murray’s character stayed in. Read TripAdvisor reviews for Royal Victorian Inn.

Princeton, Illinois

A red covered bridge near Princeton, Illinois
Photo courtesy Tim Gill via Flickr

Two hours west of Chicago, you’ll find the charming small town of Princeton. Known for its nearby covered bridges, Princeton is a lovely scenic getaway, especially in the summer and fall.

Plan a drive to see the picturesque Captain Swift Covered Bridge and Red Covered Bridge. Then take in another piece of the community’s history with a movie at the Apollo Theater, which has been in operation since 1883. 

Where to stay: The highest-rated hotel in Princeton, by far, is the AmericInn by Wyndham. Read TripAdvisor reviews of AmericInn in Princeton.

Rockton, Illinois

Historic building at Macktown Living History Museum in Rockton, Illinois
Photo courtesy aaronHwarren via Flickr

Located between Rockford, Illinois and Beloit, Wisconsin, the community of Rockton has a rich history set against a beautifully scenic backdrop. Learn about the community’s milling history with a visit to the Macktown Living History Museum. Depending on the time of year, you may even be able to experience one of the museum’s historic reenactment weekends.

Wander the nearby Nygren Wetland Preserve to experience the natural beauty this area has to offer. Then make time for some antique shopping and a trip to Historic Auto Attractions to see all sorts of famous and historic vehicles. 

Where to stay: Book a room at the gorgeous B&B, Copperstone Inn, located at Orchard Ridge Farm. Read TripAdvisor reviews of Copperstone Inn.

Pontiac, Illinois

Route 66 mural in Pontiac, Illinois
Photo courtesy Illinois Office of Tourism

Get your kicks on Route 66 in Pontiac. Learn all about the Mother Road and some of its most ardent supporters like Wall Dog Bob Waldmire at the Illinois Route 66 Hall of Fame & Museum. Don’t miss a walk around the building to snap photos with larger-than-life murals, former motel facades and even Waldmire’s former school bus mobile home. Wander the other murals along Main Street as you marvel at the Livingston County Courthouse. 

Where to stay: While it’s tempting to want a kitsch hotel along Route 66, the highest-rated hotel on several review sites is the familiar: Hampton Inn. Read TripAdvisor reviews of Hampton Inn Pontiac.

Illinois has so many charming small towns! Here are some favorites to visit for romantic getaways.

About the Guest Blogger

Megan Bannister is a freelance writer and blogger at Olio in Iowa based in Des Moines, Iowa. When she’s not sampling and writing about food, Megan enjoys visiting unique destinations, roadside attractions, and “world’s largest” things across the Midwest and beyond. Her book, Iowa Supper Clubs, highlights classic eateries past and present from around the state.

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