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The 15 Most Charming Towns in Illinois

Although Chicago is the first place that comes to mind when people think about visiting Illinois, there are lots of other travel destinations worth considering if you love small-town vibes. As someone who was born and raised in Illinois, I spent many weekends exploring what the tiny, unique towns had to offer, from mom-and-pop shops to holiday festivals and Amish culture. As you make your way through farmlands and country roads of the state, you’ll find welcoming faces, quaint B&Bs, and history to learn about.

Here are some of the most charming towns in Illinois to inspire your next Midwestern road trip.

Galena Galena, Illinois
Credit: Galena, Illinois by Chuck Kime via Flickr


One of the best small towns in the Midwest, Galena is a charming getaway in Illinois that’s full of charm and steeped in history. The town is known as a top winery destination in the region and has lots of art galleries to explore. It’s fun to plan a spa trip to Galena to treat yourself to some relaxation and browse the many antique shops for hidden treasures. You can tour the home of Ulysses S. Grant and tour the Old Market House State Historic Site. Other things to do on a trip to Galena are to join a guided ghost tour and go skiing or snowboarding in the winter. There are B&Bs that you can stay at for a romantic getaway in Galena.

Quincy The Quincy Museum
Credit: The Quincy Museum by The Quincy Museum


Situated along the Mississippi River, the Illinois town of Quincy is charming and filled with public art. You can see bald eagles in the winter and stay at cute cottages and guest houses during your trip. To learn more about Quincy, you can take a self-guided driving tour or walking tour of Maine Street Mile. There are miles of Mississippi shoreline and forests and parks to help you get outdoors and active. Other ideas for your Quincy trip are to tour historic homes, learn about agriculture at the 1930s Ag Museum, and rent a bike by the hour or day to explore the area.

Princeton Princeton, Illinois
Credit: Princeton, Illinois by © Ej Rodriquez Photography | Dreamstime.com


Princeton, Illinois is known for its covered bridges that sit just outside town. It is a historical place to visit with a quaint Main Street and Underground Railroad site. Princeton is a couple of hours west of Chicago and has festivals to check out. Some sites to see in town are the Chapel Hill Golf Course and the Soldiers and Sailors Park and Monument. Lovejoy Homestead, a historic landmark, and Hornbaker Gardens, an arboretum/botanical garden destination, are also worth visiting in Princeton.

St. Charles Pottawatomie Park on the Fox River in St. Charles
Credit: Pottawatomie Park on the Fox River in St. Charles by © Gerald D. Tang | Dreamstime.com

St. Charles

Located along the Fox River in Illinois, St. Charles is a historic town with Underground Railroad history and a trolley museum. It’s easy to get outdoors and active in St. Charles because there are miles of biking and running trails along the river and in the county forest preserves. There are six live performance venues in town, plus hundreds of bars and restaurants. Some events to check out based on your dates of travel are the St. Patrick’s parade, Scarecrow Weekend, Fox Valley Marathon, and St. Charles Jazz Weekend.

Woodstock Woodstock, Illinois
Credit: Woodstock, Illinois by © Jim Roberts | Dreamstime.com


Another quaint, small town in Illinois is Woodstock, which was made famous by the movie Groundhog Day. One of the best places to visit in Illinois, Woodstock has a historic downtown area and an opera house where you can listen to live music performances. There are lots of restaurants in Woodstock and also farms and orchards nearby where you can learn about locally grown produce. There are some fun events and festivals to check out in Woodstock, including Groundhog Days, Harvest Fest, Woodstock PrideFest, and Mexican Independence Day, as well as the farmers’ market and summer concerts.

Arthur Amish horse and buggy in Arthur, Illinois.
Credit: Amish horse and buggy in Arthur, Illinois. by © Wayne Mckown | Dreamstime.com


Arthur, the Illinois town I grew up in, is known for its Amish culture, local shops, and festivals that draw visitors from all over the area. There is a large Amish community here, which you can learn about by taking a buggy ride through the country, visiting a local farm, or shopping for Amish-made quilts, wood products, and foods. There are lots of Amish shops scattered throughout the countryside that welcome tourists. Depending on when you visit, you can join in the fun at the annual Cheese Festival or the large 4th of July celebration. It’s a popular destination in fall with the Great Pumpkin Patch just outside of Arthur to pick your own pumpkins, see farm animals, and get into the spirit of fall fun.

Ottawa Ottawa, Illinois
Credit: Ottawa, Illinois by Ottawa Illinois Visitors Center


Lots of people visit the Ottawa area of Illinois to go hiking at Starved Rock State Park. This is a beautiful park with lots of trails, rock formations, and climbing opportunities. In addition to being close to Starved Rock State Park, Ottawa is also a gateway to Matthiessen, Buffalo Rock, and Illini state parks. The town itself has Victorian homes, painted murals, and historical sites. Visit Washington Square Park to see the Lincoln and Douglas statues. Overall, Ottawa has a welcoming hometown feel and lots of local shops to check out. When you visit Ottawa, you can also spend your days with disc golf, bowling, canoe rentals, and camping nearby.

Mount Carroll Mount Carroll, Illinois
Credit: Mount Carroll, Illinois by Cragin Spring via Flickr

Mount Carroll

For small-town charm, you can also visit Mount Carroll, which has a New England vibe right here in the Midwest. It is located in northwest Illinois and has a local downtown area with an old-time, country vibe. Catch a performance at the Timber Lake Playhouse if you can. Here in Mount Carroll, you can play disc golf in the park, see motorbike racing, and visit a unique haunted house called the Raven’s Grin Inn that is open by reservation and for tours.

Geneva Geneva, Illinois
Credit: Geneva, Illinois by City of Geneva


Geneva, Illinois is a suburb of Chicago and a lovely place to visit for small-town charm. It is filled with Victorian architecture, parks, and a history museum. There’s a forest preserve here with a Japanese garden that’s worth seeing if you enjoy Frank Lloyd Wright’s design. There are lots of local shops and restaurants in Geneva, as well as public art on display and the Fox River for scenic views. Swedish Days is a Geneva festival in June that has been happening for over 70 years and has many family-friendly activities. There’s also the Geneva Arts Fair in July, the Festival of the Vine in September, and the Holiday House Tour in December.

Fulton Fulton, Illinois


One of the top sights to see in Fulton, Illinois is the Dutch-style windmill that was brought here from the Netherlands. The town is named after Robert Fulton, who invented the steamboat. There is pioneer-era history to learn about at Heritage Canyon and also outdoor recreation opportunities in the Mississippi. Visit the Andresen Nature Center to learn about local wildlife and the Cattail Park & Pavilion to go fishing, canoeing, kayaking, or paddleboarding. The Dutch Days Festival takes place during the first weekend in May to celebrate the town’s Dutch heritage. You can also spend time at the Fulton Museum and Historical Society to learn more about the area, as well as the Windmill Cultural Center, which has a collection of European windmills.

Sycamore Sycamore, Illinois
Credit: Sycamore, Illinois by © Benkrut | Dreamstime.com


Sycamore is a charming Illinois town near the Northern Illinois University campus in DeKalb. It has a beautiful courthouse with gardens surrounding it, plus a historic district with many stunning homes to see. There’s a pumpkin festival that takes place in Sycamore in the fall. Enjoy fresh apples from the Plank Road Orchard, sip drinks at the PJ’s Courthouse Tavern, and have some themed fun at Donley’s Wild West Town.

Nauvoo Sheep grazing in a pasture in Nauvoo
Credit: Sheep grazing in a pasture in Nauvoo by © Wirestock | Dreamstime.com


If you enjoy learning about local history, a trip to the charming town of Nauvoo is in order. This town was once home to Joseph Smith and has a lot of Mormon history to learn about. The Nauvoo Temple is beautifully designed and worth seeing, even if you don’t identify with the Mormon religion. You can also check out the visitor center, learn about old trades like blacksmithing, and catch summer music performances in Nauvoo. The Carthage Jail is where Joseph Smith and his brother were martyred and open to tours with a welcome center at the jail.

Dixon Downtown Dixon


Head to Dixon for a charming downtown area to shop and parks for your kids to enjoy. Dixon was the boyhood home of former president Ronald Reagan, and you can tour a house where his family lived in the 1920s. There’s an annual petunia festival in Dixon that takes place in the summer. You can get out in nature on the Lowell Parkway Trail and watch a live performance at the Dixon Theater. There’s also the Telegraph Museum and Books on First bookstore to check out as you make your way through town.

Casey The World's Largest Pitchfork in Casey, Illinois
Credit: The World's Largest Pitchfork in Casey, Illinois by © Jim Roberts | Dreamstime.com


Casey is a fun Illinois destination to visit because it is home to many gigantic objects that have made it into the Guinness Book of World Records. A local resident created these items to attract visitors and give Casey the quirky vibe that travelers have come to know and love. It’s about halfway between St. Louis and Indianapolis along Interstate 70, making it a perfect road trip stop. In Casey, you’ll find a huge rocking chair, wind chime, elevated mailbox you can actually stand inside in, and golf tee. Otherwise in Casey, you can enjoy some delicious pizza and ice cream as you check out the downtown area.

Monticello Allerton castle and park in Illinois
Credit: Allerton castle and park in Illinois by © Vladislav Gajic | Dreamstime.com


Monticello, Illinois is a small town with some unique things to do for families. Allerton Park is a nature area with trails, gardens, and a mansion that is a big draw to the area. There are historic sites to check out, including Bryant Cottage and the Monticello Railway Museum. You can hit balls at the local driving range, attend a rodeo, swim at the aquatic center, and grab a drink at the family-friendly Monarch Brewing Company. There is also an airfield here that hosts shows and events each year.

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