There are plenty of beautiful places to go in Illinois this year, but when it comes to character, history, and visual appeal, Galena consistently rises to the top. Often named among the best small towns in Illinois, Galena offers a rare combination of preserved architecture, rolling hills, and a welcoming atmosphere that feels both refined and approachable. It is the most visited small town in Illinois and ranks second statewide for tourism, right behind Chicago.
Main Street sits at the center of downtown Galena and stands as one of the most engaging places to explore in Illinois. This half-mile stretch is lined with independent boutiques, art galleries, tasting rooms, local bars, and restaurants that showcase the town’s personality. It is also where many of the best things to do in Galena come together. History lovers can tour the Ulysses S. Grant Home, while outdoor enthusiasts enjoy scenic hiking and biking trails just minutes away. From countryside views to hot air balloon rides that reveal just how picturesque this corner of the Midwest can be, it’s easy to see why Galena is rated as one of the most meaningful places to go in Illinois.
Galena may be one of the best small towns in Illinois, but did you know it’s also home to the best Bed and Breakfast in the country? Jail Hill Inn offers a one-of-a-kind Galena Bed and Breakfast experience that feels elevated, comfortable, and deeply connected to the town’s story. Housed in a beautifully restored 135-year-old former jail, the Inn blends modern luxury with thoughtful design and warm hospitality; details that earned it recognition as the #1 Bed and Breakfast in the country, and the #2 Bed and Breakfast in the world.
When you stay at our Bed and Breakfast in Galena, IL, you’re just steps from Main Street and all the things to do in Galena, making us not only a luxurious place to stay, but a convenient one as well. Book your weekend getaway in Illinois today!
Why Galena is One of the Best Small Towns in Illinois
Galena is widely regarded as the best small town in Illinois, and the reasons become clear almost immediately. The town’s history dates back to the early nineteenth century and is thoughtfully preserved through its architecture, landmarks, and walkable streets. From the moment you arrive on Main Street on your way to our Galena Bed and Breakfast, it feels like stepping into a place where history comes alive. The setting is visually striking as well, which only adds to Galena’s reputation as one of the best small towns in Illinois.
Galena sits within the Driftless Area, a unique region of the Midwest that escaped glacial flattening during the last ice age. This created rolling hills, wooded bluffs, and scenic overlooks that feel unexpected for small towns in Illinois. While simply being here is rewarding, there are also countless things to do in Galena. Below are some of the most memorable ways to enjoy a couple’s getaway in Galena.
Our Favorite Things to Do in Galena, IL
- Discover unique boutiques, art galleries, and local cafes throughout downtown Galena, all just a short walk from our Bed and Breakfast. Shopping and browsing these unique, independently owned shops is one of the most loved things to do in Galena, IL.
- Take a tour of the Ulysses S. Grant Home, one of the most historically significant attractions in the state and a must-visit when exploring small towns in Illinois.
- Enjoy sweeping views of Galena’s rolling hills from above during a hot air balloon ride, one of the most talked-about things to do in Galena. If you’d prefer to stay a little closer to town, consider Long Hollow Canopy Tours and zipling over the trees.
- Go for a scenic hike through Galena’s parks and trail systems, including Horseshoe Mound, where panoramic views stretch across the countryside, and the town’s historic skyline appears on clear days.
- Experience local craftsmanship and flavor with wine tastings at Galena Cellars and Massbach Ridge Winery, both located downtown, or visit nearby vineyards during guided wine tours around Galena.
- Bike along the Galena River Trail, where peaceful views of farmland, water, and the town’s skyline create one of the most relaxing outdoor experiences in the area.
- Play a round of golf at popular local Galena golf courses, including Eagle Ridge Resort and Woodbine Bend Championship Golf Course, both well-regarded among places to go in Illinois for golf enthusiasts.
- Spend time along the Mississippi River just a short drive from our Galena Bed and Breakfast. From visits to Mississippi Palisades State Park, a favorite for hiking, birdwatching, and nature-focused things to do in Galena, to narrated Mississippi River cruises, this is a great way to spend your time in one of the best small towns in Illinois.
The Best Bed and Breakfast in Galena, IL
When choosing places to stay in Galena, Jail Hill Inn offers a memorable experience that reflects the character and quality of the town itself. Consistently recognized as the top Bed and Breakfast in Galena, the Inn is known for combining thoughtful design, comfort, and genuine hospitality in a way that feels personal, and exactly what you’d expect from small towns in Illinois.
Set inside a beautifully restored former county jail, Jail Hill Inn features six expansive suites, each designed with space and privacy in mind. Guests enjoy king-size beds, jetted spa tubs, fireplaces, and carefully selected bath amenities, creating a stay that feels refined. Mornings begin with a multi-course breakfast, while afternoons bring wine and small bites delivered directly to your suite. Shared spaces such as the courtyard, lounge, and upper deck offer quiet places to relax between outings. A newer addition, the on-site massage room, gives guests the option to unwind even further with individual or couples treatments.
Located just steps from Main Street, Jail Hill Inn makes it easy to explore shops, dining, and many of the most popular things to do in Galena. For those looking to experience one of the best small towns in Illinois with a stay that is well considered, don’t wait to book your stay at our top-rated Bed and Breakfast in Galena, IL.
