Event Details
CHICAGO (September 2026) — Raise a stein to fall as the 2nd Annual Old Town Oktoberfest returns to Wells Street Friday, Sept. 18 through Sunday, Sept. 20, bringing three days of Bavarian-inspired food and drink, live entertainment, stein-holding competitions and family activities to one of Chicago’s most historic neighborhoods.
Following a successful inaugural year, Old Town Oktoberfest celebrates the German immigrant heritage that helped shape the neighborhood while building a new fall tradition for today’s Old Town community. The festival takes place on the 1300 block of North Wells Street, between Schiller Street and Evergreen Avenue, across from Cobbler Square Lofts, the former Dr. Scholl’s factory.
BRATWURST, PRETZELS, GERMAN BEER — AND MALÖRT TRUFFLES
Classic Oktoberfest flavors take center stage throughout the weekend. Festivalgoers can dig into Paulina Market bratwurst served on a pretzel bun with sauerkraut and grilled onions, along with warm Bavarian-style pretzels from a special Old Town Oktoberfest menu.
Neighborhood favorite The Fudge Pot will put a distinctly Chicago spin on Oktoberfest sweets with taffy apples rolled in pretzels and Malört-filled truffles.
Wash it all down with ice-cold German beer or warm up with hot spiced wine while enjoying the sights, sounds and community atmosphere of Oktoberfest on Wells Street.
LIVE MUSIC, STEIN-HOLDING AND FAMILY FUN
Live entertainment will fill Wells Street all weekend, from German-inspired music and brass to popular Chicago festival bands spanning multiple genres, inviting plenty of dancing and singing along the way.
Festivalgoers can also test their strength in Masskrugstemmen, traditional stein-holding competitions held throughout the weekend, with prizes and bragging rights on the line.
Football fans can catch the weekend’s action on a giant outdoor screen, while families can enjoy games, caricatures and pumpkin painting.
NEW THIS YEAR: OKTOBERFEST DOG PARADE
Adding to the weekend festivities, four-legged Oktoberfest fans will get their turn in the spotlight during the first Old Town Oktoberfest Dog Parade on Sunday, Sept. 20 at 11 a.m.
Dogs and their humans are invited to strut Wells Street in their best Bavarian and fall attire, with costumes strongly encouraged. Expect plenty of lederhosen, dirndls and creative dog-and-owner ensembles.
Pups can register in three categories:
Wee Wieners — Small breeds, up to 30 lbs.
Pretzel Pups — Medium breeds, 31–70 lbs.
Big Bratwursts — Large breeds, 71 lbs. and up
“Old Town’s German history is an important part of our neighborhood’s story, and Oktoberfest gives us a chance to celebrate that history while creating a new tradition for today’s community,” said Marcy Huttas, Executive Director of the Old Town Merchants & Residents Association (OTMRA). “We want people to come for the music, bratwurst and beer, but also spend the weekend discovering the businesses, architecture and character that make Old Town such a special part of Chicago.”
EVENT DETAILS
WHAT: 2nd Annual Old Town Oktoberfest
WHEN: Friday, Sept. 18–Sunday, Sept. 20, 2026
HOURS: Friday, 5–10 p.m.; Saturday, 11:00 a.m.–10 p.m.; Sunday, 11:00 a.m.–8 p.m.
WHERE: 1300 block of North Wells Street, between Schiller Street and Evergreen Avenue, Chicago
ADMISSION: $10 suggested gate donation
INFO: oldtownchicago.org/events/2026-oktoberfest/
Gate donations help offset festival expenses, including performers, security, event staff, cleaning and logistics, while supporting OTMRA’s year-round work on behalf of the Old Town community.
ENTERTAINMENT SCHEDULE
Friday, Sept 18
5:30pm – Recorded Music / Stein Holding Competition #1
6:00pm – Four Star Brass Band
7:15pm – Stein Holding Competition #2
8:00pm – Hello Weekend
Saturday, Sept 19
11:00am – Apasionado Duo
12:00pm – Four Star Brass Band
1:15pm – Stein Holding Competition #1
1:45pm – Second Hand Soul Band
3:15pm – Stein Holding Competition #2
3:45pm – RAVIV
5:00pm – Stein Holding Competition #3
5:30pm – Run Forrest Run
7:00pm – Stein Holding Competition #4
7:45pm – Funky Monks: Red Hot Chili Peppers Tribute
Sunday, Sept 20
11:00 am – First Old Town Oktoberfest Dog Parade
12:30pm – School of Rock
1:30pm – Stein Holding Competition #1
2:00pm – Bratwurst Brothers
3:15pm – Stein Holding Competition #2
3:45pm – Live Band Karaoke
5:15pm – Stein Holding Competition #3
5:45pm – Stache
ABOUT THE OLD TOWN MERCHANTS & RESIDENTS ASSOCIATION
The Old Town Merchants & Residents Association (OTMRA) connects area residents, small businesses, and cultural organizations. Old Town is a neighborhood rich in multigenerational family businesses, comedy, architecture, great food and drink, and more. Our goal is to continue Old Town’s evolution as a safe and vibrant location to live, work and laugh. Learn more about OTMRA as well as Old Town’s unique shops and restaurants by visiting oldtownchicago.org.
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