3 Small Towns in Illinois So Dreamy, You’ll Swear You’ve Seen Them on TV

Growing up in the Prairie State, I had the distinct privilege of discovering dreamy small towns in Illinois. Illinois is nearly 400 miles long, and there are seemingly endless adorable small towns scattered throughout the state. While this list could go on forever, below are a trio of my personal favorite small towns as a homegrown Illinoisan.

1. Galena

Galena, Illinois, is one of the most beloved small towns in the state. With many of the community’s restored homes on the National Register of Historic Places, it often feels like you’ve stepped back in time to the 1800s. Plus, Galena was home to a Civil War general turned president, Ulysses S. Grant. My favorite place to stay in Galena is the DeSoto House Hotel. Future President Lincoln actually spoke from the DeSoto House’s Main Street balcony in 1856 to support a colleague's bid for the presidency. In addition to all the incredible Illinois history in Galena, the area is home to some great wineries, such as Fergedaboudit Vineyard and Winery and Galena Cellars Winery. If you don’t think of Illinois as wine country, I encourage you to think again! Finally, as an avid skier, I can never say no to a day on the slopes at Galena’s Chestnut Mountain Resort.

2. Oregon

Since I was a little girl, my family has been taking weekend trips to Oregon, Illinois. This truly under-the-radar community sits on the Rock River and offers endless opportunities to get lost in nature. Its most iconic landmark is the 50-foot Eternal Indian Statue, but it is more commonly referred to as the Black Hawk Statue, which overlooks the river. Every autumn, my family would make the trip to Oregon to attend the Autumn on Parade fest, stay overnight at the Paddle Wheel Inn, and enjoy a morning breakfast cruise on the Pride of Oregon (I can still smell the delicious, warm, and gooey orange rolls!). The town is also close to four state parks, including my personal favorite, White Pines Forest State Park.

3. Hinsdale

I grew up a town over from Hinsdale, Illinois. Just a short train ride outside of Chicago, Hinsdale is a west suburban community that often feels like you’ve stepped into a scene from Leave It to Beaver. Family is the priority here, and investing in the community comes right with it. Downtown Hinsdale is beautifully preserved, filled with upscale mom-and-pop shops and restaurants. It’s a lovely little community for shopping and enjoying the quiet, suburban greenery with a walk around the main drag. What I particularly appreciate about it is that if you’re coming from Chicago, the train drops you off in the heart of Hinsdale, so you don’t need to drive or deal with parking.

​Each of these three dreamy small towns in Illinois holds a special place in my heart. Whether it's the nature of Oregon, the history of Galena, or the comfort of Hinsdale, these communities deserve a spot on your Illinois bucket list. Feeling inspired? Try planning your own Illinois trip using Only In Your State’s itinerary planner.