/  North America   /  United States   /  Illinois   /  
sycamore - The Most Charming Small Town in Illinois

The 10 Most Charming Small Towns in Illinois (2021)

Illinois is one of the most beautiful midwestern states, and every American will agree to that. Another unarguable fact is that there isn’t anything better and beautiful than Chicago in Illinois. Chicago holds 1/4th population of the State and is one of its biggest draws. However, do you know the majority of Illinois is not metropolitan but rolling plains, tight-knit communities, villages and small towns? Yes, you read it right.

Illinois is home to some amazingly charming small towns. These small towns will proximate you to a new bright world and at the same time will make you feel at home. Whether you are planning for a quick day trip or a weekend getaway in Illinois, options here are in abundance.

The 10 Most Charming Small Towns in Illinois

Here are some of the best small towns in the American Midwest. No matter what kind of traveller you are, you cannot simply miss being here.

1. Woodstock

One of the most charming small towns in Illinois, Woodstock seems similar to everyone who arrives here. All thanks to movies like Trains and Automobiles & Groundhog Day and Planes. However, this small town is even a notch better than how it was picturized. The entire downtown Woodstock claims in the National register of historic places, and thus there’s a lot to do and explore. On a bright sunny day, one can step out to eat, shop, get entertained or simply walk around. Locals here are extremely warm and friendly and makes everyone feels welcomed. While you decide to visit Woodstock, consider being part of their folk festival organized every 3rd Sunday of July.

2. Elsah

Elsah is a beautiful small town, voted as the top scenic spot in Illinois. The entire town is listed in the National Register of Historic places and is heaven for history buffs. Also known as “village where time stood still”, Elsah is simply gorgeous. Everything holds an undisputed charm, from its 18th-century building to the views down to the Mississippi River. It is also one great stop for architectural buffs who are looking to stop and explore the historic homes around. Though commonly, the individuals from the neighbourhood visit here either to ride the Sam Vadalabene Bike Trail or to spot a bald eagle.

3. Greenville

One of the oldest communities in Illinois, Greenville has seen more than two centuries now. The town has a handful of museums that proudly narrates its beautiful history. One can begin with the American Farm Heritage Museum to Richard Brock Museum and end with the Demoulin Museum. While strolling through Downtown Greenville, you will come across a large stone memorial. It is where Stephen Douglas and Abraham Lincoln wrote their presidential speeches in 1858. Greenville is popular for its festivals like the Agape Music Festival & the World Powered Parachute championship.

4. Mount Carroll

Also known as the New England of Midwest, Mount Carroll is a charming small town to visit in Illinois. It is reportedly the coldest town in Illinois, where winters have touched as low as -38-degree Fahrenheit. However, in contrast, summers rise as high as 85 Fahrenheit, comfortable enough to walk around. To cover everything in this small town, visitors often choose biking or cycling around. While strolling down the lanes, you will find a bohemian vibe as the population of 1,500 consists of some great artists. Locals of Mount Carroll have made sure to maintain the town as young as fresh as it was nearly a century ago. Every single day here will make you feel like walking right into the past and living it fully.

5. Galena

Galena is an Illinois small town that everyone has heard and read of. It is by far one of the most visited and famous towns in Illinois. While the streets here are painted into history, it’s quintessential downtown makes it iconic. When in the Galena, you can stay in the DeSoto house hotel, which claims to be the oldest hotel in Illinois. From civil war general to several U.S. presidents, it has hosted several notable personalities of the time. Tighten your shoes and step out for hiking the peaceful Galena River trail. Or take your partner along and get along exploring wineries, historic homes, or the spooky ghost tours.

6. Princetown

Princetown was settled in the early 1800s and is by far the most picturesque town in Illinois. It is located 2 hours west of Chicago and is notedly a go-to weekend getaway spot for the locals. Princetown has so much to offer, from its historic downtown to parks, seasonal festivals, public golf courses, and whatnot. One of the highlights here is the two covered bridges, one historic while the other contemporary. However, Princetown doesn’t stop there. It is also home to an underground railroad, the Lovejoy homestead, and the historic Apollo Theater.

7. Sycamore

A is a city in DeKalb County; Sycamore holds all charms of a small town. It is a commercial city in proximity to Chicago, but the tourism seen here are equally well. With its warm and sophisticated hospitality, Sycamore sends every visitor back full of satisfaction. The city is famous for its annual Pumpkin Festival happening here since 1962. The festival is full of art, craft, food, parade, extensive pumpkin display and full-on entertainment. If you are here during the apple season, make sure to walk around the Plank Road Orchard and pluck your own fruit. They grow 17 different varieties of the juiciest and tastiest apples of Illinois.

8. Fulton

If you want to have some peace under the Sun, do visit Fulton. This small town in Illinois has strong Dutch roots and a distinctly Dutch vibe. The Dutch windmill brought here from the Netherlands to the Dutch Days festival will soak you in vibes. Being with some shopping and eating at the quaint Fulton Downtown and then take a walk-through Heritage Canyon. Or if you are in a mood to sit and enjoy, fish and boat along the Mississippi River. Weekends at Fulton are full of windmill tours, food, culture, eating, dancing along with art and craft. For a quick refreshment from your daily life, plan a weekend trip to Fulton, Illinois.

9. Nauvoo

Nauvoo is a tiny historical town located in Hancock County, Illinois. Back in the 1800s, it has a population the same as Chicago, though today, there aren’t any more than 1300 residents. However, this isn’t what describes the city. Nauvoo is popular for its historical significance and its peaceful beauty surrounding it. Everything is visit-worthy from Joseph Smith Homestead, Red Brick Store, the Smith Family Cemetery, and the Nauvoo House. The Nauvoo Temple is pone great stop if you are looking for some spiritual peace on your trip. This small town is also one of the best stops for antiques in Hancock County. Everything here comes for small and big auctions and are in pretty great condition. Do consider taking one or two along.

10. Rockton

A truly Midwestern village, Rockton is a must-visit when in Illinois. It is located in Winnebago County and is home to several historic buildings from the 1800s. Today these building serves as ice cream parlours, Dairy Haus, bakeries and several other running businesses. While walking through the lanes of Rockton, visitors often hop over the border (only a few miles away) to fill their stock of New Glarus beer. It is one of the rare treats that is rare to find anywhere else easily, so do not afford to miss it. Historic buffs can stop to explore the George H. Hollister House or opt for the Historic Auto attraction tours. Rockton is an ideal place for a quick day exploration.