If you’re ever visited us in Galena, you probably know that Galena hosts a variety of fun events and activities throughout the year. In fact, there are so many great Galena IL upcoming events, that we thought we’d help you do a little advanced planning. It probably comes as no surprise that we book up quickly for the most popular of Galena’s events, which include the Wine Lovers Weekend, Corkless in Galena, Halloween, Nouveau Weekend, and the Night of the Luminaria & Living Windows around the holidays.

We always encourage our guests to book early and book often. It’s no different in 2020 when we’re already seeing plenty of advanced bookings for events and weekends our previous guests simply don’t want to miss.  So, if you have your heart on attending one of these Galena IL upcoming events, head on over to our website and book your room today!

10 Must-Do Galena IL Upcoming Events

One of the best things about Galena is how close by and easy it is to get to for much of the Midwest. It’s a one-tank get away from big cities like Chicago and Milwaukee, but also within easy driving distance from cities like Minneapolis/St. Paul, Madison, Des Moines, and even as far away as St. Louis and Indianapolis.

Aside from just how easy it is to get here, visiting Galena is like visiting another world, preserved from a different time and place than the modern world we now find ourselves in. Galena is a historic city nestled on the banks of the scenic Galena River, in the hilly countryside you typically don’t find in the midwest. It’s beautiful here, and it’s quintessentially romantic.

This, of course, is all made better by the fun-loving residents who live and work here, and who’ve made Galena into the incredible destination that it is today.  If you’re feeling ready to visit–and we don’t blame you if you’re ready to hop in the car as we speak–then here are the 10 Galena IL Upcoming Events to plan for!

1. Wine Lovers Weekend, March 27 – 28, 2020 (we’re already sold out for 2020, but 2021 dates have been released as of March 26 – 27, 2021!).  Wine Lover’s Weekend is one of Illinois’ largest indoor wine tastings, featuring over 250 wines.
2. The Great Galena Balloon Race, June 19 – 21, 2020, is a 3-day event that features stunning ballooon glows, hot air balloon rides, and plenty of fun.
3. The annual Corkless in Galena event is one not to miss, and this year it takes place on June 27, 2020. It’s an event filled with wine tastings, art exhibits, food, and great music. It’s a celebration of the wines and food of Northern Illinois, and something our guests look forward to each year.
4. The annual NW IL Art and Jazz Fest will take place on July 18 – 19, 2020, and features two days of regional fine art, live jazz music and scrumptious local food, craft beer & wine.
5. The annual and much-loved Tour of Historic Homes will take place on September 26 – 27, 2020.
6. Galena’s 14th annual Oktoberfest will take place on October 3, 2020. Come have a pint with us, and help Galena celebrate!
7. The annual Halloween Parade and Festival will take place on October 31, 2020, and is always a spectacularly good time!
8. Raise a glass and celebrate the release of Galena Cellars’ Nouveau wine with the annual Nouveau Weekend celebration, taking place November 20 – 21, 2020.
9. Galena’s annual Holiday Fire in the Sky event kicks off the holiday season in true style on December 3, 2020.
10. The year ends with one of the most popular events of the year, the Night of the Luminaria and Living Windows, on December 12, 2020. It’s one of the most beautiful and romantic nights of the year in Galena when more than 30 windows come alive with holiday-inspired animation, and lighted luminaries light the way from one end of town to the other.

Stay at our Galena Bed and Breakfast

There is, of course, nowhere better to stay for these Galena IL Upcoming Events than our luxurious Bed and Breakfast. From a delicious gourmet breakfast in the morning to the comfortable sheets awaiting you at the end of the day, there’s nothing that goes unnoticed during your time at the Jail Hill Inn.  Come see what sets us apart from the rest, and book your room at Galena’s #1 Bed and Breakfast today!