This Underrated Midwest Town With Cozy Inns, Local Wineries, And Historic Charm Is A Top Illinois Getaway

Hidden away in the northwestern corner of Illinois — just minutes from both Iowa and Wisconsin — is the charming Galena. It might be hard to believe, but this tiny town of 3,000 sees nearly a million annual tourists. Locals know Galena as a trendy destination, but anyone beyond the Midwest might see it as just another small town. However, that couldn't be further from the truth. With an authentic downtown bursting with old-school charm, highly rated wineries, and a rich history to explore, Galena is one of the best getaways in Illinois.

Part of what makes Galena so special is its natural geography. Unlike much of the state, which was flattened by glaciers, Galena remained widely untouched. The region, known as the Driftless Area, features a wealth of bluffs, hills, and waterways, making Galena a feast for the eyes compared to the rest of Illinois' cornfields. You'll also be close to other iconic Driftless towns, including an underrated waterfront gem along the Mississippi River.

As for how to reach Galena? Consider flying into the Quad Cities International Airport just over an hour south. If you don't mind an epic two-hour road trip and want to see the incredible streets of Chicago, then you can fly into O'Hare or Midway. This also gives you a chance to explore an underrated Japanese-inspired lakeside garden in Hyde Park.

With dozens of its buildings holding historic significance, it doesn't take long to fall in love with Galena's nostalgic charm. Strolling down Main Street is one of the first things you'll want to do upon arrival — and while it won't take long to see everything it has to offer, you can extend the walk by venturing onto the nearby Galena River Trail and enjoying the Galena River. Galena Cellars Vineyard is one of the most popular wineries in town, and since it has an elegant tasting room right on Main Street, be sure to stop in and grab a glass.

Fried Green Tomatoes is another local favorite. Featuring historic exposed brickwork and housed inside a building previously owned by General Grant's father, it's an upscale destination that combines Galena's history with innovative dishes. Other must-visit restaurants include the lively Blaum Bros. Distilling Company, the affordable Dillon's and its huge portions, and the Italian delicacies of Vinny Vanucchi's.

As for where to call home during your getaway? Consider booking a room at Stoney Creek Inn or the Farmers Guest House. The former is a regional chain with premium destinations throughout the Midwest, and its Galena accommodations are bursting with local charm. It's also steps from a grocery store for added convenience. The Farmers Guest House, meanwhile, is a bed and breakfast just a stone's throw from downtown, featuring sophisticated décor and a laidback vibe.

Galena derived its name from the scientific term for lead sulfide, the mining of which was a massive economic driver for the town during the 1800s. This led to all sorts of tourism and travel opportunities — including visits from Abraham Lincoln and Stephen A. Douglas, who held speeches at the DeSoto House Hotel. This location is still a functioning hotel, so consider booking a room here if you want to immerse yourself in Galena's history.

Another way to enjoy the historic roots of this charming Driftless Area town is by taking a trolley tour. These adorable red and gold vehicles chauffeur you through its cobblestone streets and storied roadways as you glimpse its many historical sites. Places you'll see include President Grant's home, Galena's oldest stone structure that was built in 1826, the home of Congressman E.B. Washburne, and plenty of stately Victorian-era buildings.

Consider exploring Depot Park and Grant Park on foot, as there are plenty of statues and informational displays to peruse. This includes a monolithic Civil War Monument and historic cannons like the Blakely Rifle and German Krupp Howitzer. This is also where you'll find two gorgeous footbridges crossing the Galena River and connecting you back to downtown. Want to explore another historic town in the Driftless Area? Head north two hours to an artsy, underrated community bursting with Norwegian charm.