Drive about 2.5 hours west of Chicago towards the Mississippi River, and you’ll find one of the most well-preserved historic and charming towns in the Midwest. Galena, Illinois, is home to just over 3,000 people, but you’d never know it. It’s the second most popular destination in Illinois, behind only Chicago. Despite its small size, you’ll find so many fantastic things to do in Galena, IL.
History is just the beginning of things to do in Galena, IL. Here, you’ll find historic attractions like the Ulysses S. Grant Home, plenty of antique stores to browse, a fantastic array of shops, boutiques, and eateries to enjoy downtown, and miles of hiking and biking trails in the rural, hilly countryside, too. It really does have it all and is undoubtedly one of the best Midwest towns for weekend getaways!
Whether you’re looking for upscale lodging for a relaxing and romantic getaway in the heart of Galena or a quiet retreat in the scenic countryside, there are no better places to stay in Galena than our local lodging partners. As with all member properties of the Midwest Association of Independent Inns, these Galena lodging partners offer exceptional accommodations and world-class hospitality. They are eager to share with you all the best things to do in Galena, IL, no matter the time of year you visit.
Browse through our incredible selection of Galena Bed and Breakfasts and hotels, then book your stay and get ready to explore America’s most charming small town with us.
The Top Things to Do in Galena, IL
Most of downtown Galena is listed on the National Registry of Historic Places. Few towns are dedicated to historic preservation like this one, and that’s in large part what gives Galena such a charming sense of place. You’ll immediately feel whisked away to a different time and place. Here, time slows down, and the weight of your daily stress feels a million miles away. While Galena may be best known for its historical character, you’ll find plenty more things to do in Galena, IL, than learning about the past.
There is, after all, a reason visitors come back to this town time and time again. There’s something for everyone here, and its scenic beauty and friendly locals make the town a spectacular Midwest getaway destination. From fun shopping and historical tours to exciting outdoor adventures, we hope you join us in exploring the best of Galena this year. Below, we’ve curated a list of some of our favorite things to do in Galena, IL.
- There’s no doubt that one of the best things to do in Galena, IL, is to shop. Main Street in downtown Galena has over 100 unique and independently owned shops and boutiques. You can find all sorts of fantastic gifts and treasures – but even if you don’t buy anything, browsing and visiting with the shop owners is a wonderful way to spend a day!
- Get oriented to town and learn all about its fascinating history on one of the Galena Trolley Tours.
- Given the town’s historic nature, you can’t miss visiting Galena’s top historic attractions, which include the U.S. Grant Home, the Dowling House, and the Belvedere Mansion.
- If you want to stretch your legs a bit or ride a bike through gorgeous scenery, head out on the Galena River Trail. It’s a rail-to-trail conversion and is one of our favorite ways to experience Galena’s beautiful scenery.
- For even more great scenery, head to a local Jo Daviess County Conservation Property for a hike. Visiting parks like Horseshoe Mound Preserve is one of the most beautiful things to do in Galena, IL.
- If you’re here in the winter, don’t miss skiing at Chestnut Mountain Resort. It’s one of the best things to do in Galena, IL, in the winter, but this old-school ski resort is also a great place to visit in the summer! It has a fun mountain adventure park and offers narrated scenic cruises on the Mississippi River.
- Enjoy a bit of wine tasting in the countryside surrounding Galena. Galena Cellars and Massbach Ridge Winery offer tasting rooms in downtown Galena, but there are also wine tours that will take you to vineyards in the countryside for a fun afternoon.
- How about a fun adventure? For thrill-seekers, one of the best things to do in Galena, IL, is to go ziplining with Long Hollow Canopy Tours. It’s beautiful in the summer but breathtaking in the fall!
- How about unique things to do in Galena, IL? The town has plenty of history, which also means plenty of opportunities for ghost stories! While in town, make sure to take a ghost tour!
- Things don’t slow down in the evenings in Galena! There are plenty of bars with live music and entertainment, but one of the most unique things to do in Galena, IL, in the evenings is to attend a show at P.T. Murphy’s Magic Theatre.
There are, of course, far more things to do in Galena, IL, than this small list suggests. We hope you take the time to visit this fantastic Midwest town to discover more!
The Best Places to Stay in Galena, Illinois
As you can see, like so many small towns in the Midwest, there is a surprising array of fun things to do in Galena, IL – and our member properties are your headquarters for all of it. There are several fantastic Galena Bed and Breakfasts, Hotels, and lodging properties ready to welcome you to town, treat you to exceptional hospitality, and share with you their favorite parts of their town. Much like the welcoming vibe of the town, you’ll find our Galena lodging properties offer a warm, authentic slice of Midwest hospitality.
The Midwest Association of Independent Inns features some of the top places to stay in the Midwest. Whether you find yourself in Galena or beyond this summer, our association is one of the largest of its kind, offering Midwest travelers a one-stop destination for all your lodging needs. Beyond providing exceptional hospitality, each member’s property is properly licensed, unlike many Airbnb and other vacation rental properties. They have also been inspected, ensuring you have a safe, clean, and comfortable place to stay in the Midwest.
In addition to exceptional, detail-oriented hospitality, you can expect a lodging experience that is as unique as your vacation. Unlike modern hotel chains, our properties bring character back to your vacation. Though our member properties may all excel in hospitality, each of them brings something unique and wonderful to your lodging experience. We have no doubt you’ll leave with lasting memories—not just of the places you go and the experiences you have, but of the people you meet along the way, too.
Join us at these incredible Illinois Bed and Breakfasts and hotels, and get ready to experience all the best things to do in Galena, IL, this summer. Book your stay with one of our local properties today!
