If you love to plan for upcoming events, we have 8 perfect ones to plan for in the historic town of Galena! Galena is situated in the beautiful Driftless region of Illinois, surrounded by lush rolling hills and breathtaking scenery. Located about 3 hours away from Chicago, Milwaukee, and Des Moines, it’s the perfect one-tank getaway destination for many in the Midwest.  This is part of what makes Galena such a popular vacation destination, but location is not everything. Galena also happens to be an incredibly charming, historic town, with a variety of delightful shops to explore, restaurants to savor, and activities to keep you busy.  The city is home to fewer than 3,500 residents, but this beautiful and charming little town attracts more than a million guests each year with a full events calendar and plenty of attractions. It really is like no where else in Illinois, and once you discover it, we have no doubt you’ll keep coming back again and again. Come experience a luxurious slice of Galena, and stay at our restored Bed and Breakfast, recently voted as the #1 Bed and Breakfast in the country, and #2 in the world.

8 Upcoming Events in Galena to Plan for

Beyond Galena’s historic charm, quaint atmosphere, and welcoming community, there are plenty of reasons to visit us at the Jail Hill Inn.  With tourism being such a major part of our local economy, Galena has curated an extensive list of upcoming events and attractions to keep guests busy and happy.  Here are 8 great upcoming events to consider as you plan your next getaway to Galena:

• U.S. Grant Pilgrimage, April 26, 2019.  The U.S. Grant Pilgrimage is a weekend full of celebrations for Ulysses S. Grant’s birthday. Activities include Civil War reenactments & encampment, and a parade down Galena’s Historic Main Street.
• Ride the Ups and Downs, May 4, 2019. A one-day bicycle tour of beautiful Galena, featuring plenty of hilly terrain and spectacular panoramas along the way.
• Galena River Wine & Cheese Portfolio Tasting, May 18, 2019. This is a great chance to sample more than 70 wines, artisan cheeses, and craft beers. Tickets include a commemorative wine glass, a tasting program, and special discounts at Galena River Wine & Cheese.
• Great Galena Balloon Race, June 21, 2019.  This 3-day event is the perfect chance to get up close to hot air balloons and learn all about them. This event features more than 20 hot air balloons, three races, a night glow extravaganza, a car show, live music, an art show, and more.
• Corkless in Galena, June 22, 2019. Celebrate the wines and food of Northern Illinois and beyond, with unique wines produced by family-owned Northern Illinois Wineries.
• NW Il Art & Jazz Fest, July 20, 2019. This annual event features two days of regional fine art, live jazz music and scrumptious local food, craft beer & wine, and was named Best Festival by Illinois Country Living readers in 2017.
• Market Square Arts Festival, August 10, 2019.  This annual outdoor art festival features a variety of local and regional artists showcase their paintings, woodwork, jewelry, pottery, baskets, and more.
• Tour of Historic Homes, September 28, 2019. This is a wonderful chance to explore the historic homes of Galena, with a guided tour of five private historic homes open only for this weekend.

Many of these upcoming events have become beloved community celebrations over the years, and guests return year after year for the most popular of them. It’s always good to book your room at our luxury Bed and Breakfast early and to check Galena’s upcoming events calendar when planning a vacation. Beyond these upcoming events, there are countless other reasons to visit us in Galena this summer. Book your room at our luxury Bed and Breakfast today!