Prost to a new fall tradition!
You might be surprised to learn that Old Town is actually Chicago’s first German neighborhood, yet it has never hosted Oktoberfest celebrations—until now.
This weekend, Old Town is hosting its inaugural Oktoberfest on Wells Street from Friday, September 19, to Sunday, September 21, 2025. The festival promises a delightful blend of Bavarian culture, local flavor, and community spirit.
Fest attendees will enjoy lively entertainment, including German-inspired music, a brass band, polka, and some of Chicago’s top festival bands across various genres. Plus, catch the football action on a giant outdoor screen and test your strength in Masskrugstemmen (stein-holding contests) for a chance to win prizes.
The Old Town Oktoberfest menu features bratwurst with sauerkraut, pretzels, potato pancakes, and fried cheese, along with taffy apples, fudge, and a funnel cake, as well as hot spiced wine.
Marcy Huttas, Executive Director of the Old Town Merchants & Residents Association, said:
Early German immigrants played a key role in shaping the cultural identity of our neighborhood. We are excited to establish this new tradition and encourage attendees to explore all that Old Town has to offer. The $5 suggested gate donation will help make this an annual neighborhood event for all to enjoy.
Where is Old Town Oktoberfest?
The Old Town Oktoberfest will be held at 1360 N Wells St. The festival hours are as follows: Friday from 5:00 pm to 10:00 pm, Saturday from 11:30 am to 10:00 pm, and Sunday from 11:30 am to 8:00 pm, taking place from September 19 to 21.
The festival is located on the 1300 block of North Wells, between Schiller and Evergreen streets, across from Cobbler Square Lofts, which was formerly the Dr. Scholl factory.
Old Town Oktoberfest music schedule
Friday
- 6:00 pm – Four Star Brass Band
- 8:15 pm – Dancing Queen: An ABBA Salute
Saturday
- Noon – String Music by Classical German Composers
- 1:30 pm – Live Band Karaoke (where you become the star!)
- 4:00 pm – Four Star Brass Band
- 6:00 pm – Rosie & The Rivets
- 8:00 pm – Super Creeps: The Music of David Bowie
Sunday
- Noon – String Music by Classical German Composers
- 2:00pm – Die Musikmeisters
- 3:30 pm – Recorded Music
- 4:00 pm – Big City Nights (Scorpions Tribute)
- 6:00 pm – Stache