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Best Place to Stay in Galena: Jail Hill Inn

Just over the border from Wisconsin, nestled among the rolling hills of Illinois, lies Galena—a picture-perfect town where my partner and I escaped for a weekend getaway. Our stay at the Jail Hill Inn, a cozy retreat crowned as the Best Bed & Breakfast in the United States in 2019, was nothing short of enchanting. From the warm hospitality shown by the innkeeper to the morning feasts that became the highlight of our days, this place felt like a slice of home away from home.

Every morning at Jail Hill Inn began with an extraordinary breakfast that set the tone for the day—think gourmet dishes served with a side of lush garden views, setting an almost storybook scene for our morning coffee.

Strolling Through Historic Downtown Galena

Strolling through Galena’s historic downtown was like stepping back in time with its well-preserved 19th-century buildings. We popped into quaint shops and stopped by Galena Book & Paper, a charming local bookstore that became an instant favorite for its curated selection and cozy atmosphere. For a caffeine fix, Kaladi’s Coffee Bar was our go-to, where the vibe was as vibrant as the coffee was rich.

Galena Dining Recommendations

Dining in Galena was another treat, with Charlie’s Place Eatery providing hearty breakfasts and lunches that fueled our explorations. Dinner was a toss-up between local recommendations, but Fried Green Tomatoes won us over with its delectable takes on classic dishes, making it our top pick over Fritz and Bistro.

 

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Unique Experiences in Galena

One of the most memorable experiences was our unique adventure with Hoof It Treks, where we went hiking with goats—a delightful way to connect with nature and each other. Read our full post about our goat trekking adventure in Galena here.  This unusual outing combined the beauty of Galena’s landscape with the playful charm of our hoofed companions, creating unforgettable memories. 

 

Exploring the Legacy of Ulysses S. Grant

We also delved into the rich history of Ulysses S. Grant, whose presence is felt throughout the town. Exploring his home and learning about his life in Galena added a historical depth to our visit, enriching our understanding of this quaint town.
We Wisconsin Tip:

While in Galena, don’t miss the chance to take a sunset stroll through Grant Park. The park, overlooking the Galena River, offers stunning views and a tranquil setting perfect for reflecting on your day or simply enjoying the moment with your loved one. Whether it’s reconnecting over a quiet walk or sharing a laugh during a unique goat hike, Galena offers countless ways to make every moment special for couples.

 

Hoof It Galena Goat Treks. Spend a day walking with goats.

WeWisconsin Tip:

While in Galena, don’t miss the chance to take a sunset stroll through Grant Park. The park, overlooking the Galena River, offers stunning views and a tranquil setting perfect for reflecting on your day or simply enjoying the moment with your loved one. Whether it’s reconnecting over a quiet walk or sharing a laugh during a unique goat hike, Galena offers countless ways to make every moment special for couples.