Festivals, Fairs & Special Events
Old Town Oktoberfest on Wells Street September 20, 2026
Chicago’s historic Old Town neighborhood raises a stein to fall as Old Town Oktoberfest returns September 18–20, 2026. Celebrating the neighborhood’s rich German heritage, this three-day street festival transforms Wells Street into a lively Bavarian-inspired destination filled with authentic food, live music, local artisans, and festive traditions.
Following a successful inaugural event in 2025, Old Town Oktoberfest returns bigger and better, inviting both longtime residents and visitors to experience one of Chicago’s most charming neighborhoods through the sights, sounds, and flavors of Oktoberfest.
Festivalgoers can enjoy authentic German favorites including bratwurst, giant pretzels, and ice-cold beer while dancing to German-inspired performers and popular Midwest bands throughout the weekend. Guests can browse curated arts and crafts vendors, compete in crowd-favorite Masskrugstemmen (stein-holding competitions), and enjoy a welcoming neighborhood atmosphere under Old Town’s iconic lights.
Sports fans won’t miss a moment thanks to the festival’s giant LED viewing area, creating another gathering space where guests can cheer on their favorite teams while enjoying the festivities.
Gate Donations ($10 suggested) help fund work in the Old Town Community throughout the year and off-set festival costs including performers, security, festival staff, cleaning, logistics, etc)
Whether attending for the live entertainment, authentic cuisine, neighborhood atmosphere, or simply to celebrate the arrival of fall with friends and family, Old Town Oktoberfest offers an unforgettable Chicago tradition that continues to grow each year.
