Old Town's Oktoberfest Is New. The German Roots Underneath It Aren't.
September 17, 2026
September 17, 2026
By Friday, September 18, Wells Street will look different than it does right now. Second City's marquee will still be pulling its usual line for the evening show, but a block up, crews will be finishing a beer tent, testing a sound system, and hanging banners for stein-holding contests. Two years ago none of that existed. This year it's back for round two, bigger than what launched in 2025.
The second annual Old Town Oktoberfest runs Friday through Sunday, September 18 through 20, on the 1300 block of North Wells, with the check-in stage set up at Schiller and Wells. Friday hours run 5 to 10 p.m., Saturday 11 a.m. to 10 p.m., Sunday 11 a.m. to 8 p.m. It's organized by the Old Town Merchants & Residents Association, the same nonprofit that runs the neighborhood's summer Wells Street Art Festival, and it's free to attend, with a suggested donation at the gate.
What's easy to miss, if you only read the festival copy, is that this isn't a themed pop-up dropped into a random commercial strip. It's happening in the one Chicago neighborhood where German immigrants actually settled first, on the same street where a family-run German wine shop has operated continuously since 1888. That distinction is the reason this festival reads differently than most of the other Oktoberfests competing for your weekend this fall.
Year one was a straightforward debut: bratwurst, pretzels, a beer garden, and live bands including a Bowie tribute act and a Scorpions cover set. Year two keeps the core format but adds two things residents specifically didn't get in 2025:
That's a small but telling shift. A one-off festival repeats itself. An organization building a real annual event listens to what people showed up for the first time and adds a reason to come back with something they didn't bring the first year, in this case a dog.
OTMRA's own framing calls Old Town "Chicago's very first German neighborhood," and that's not marketing language stretched to fit a beer festival. German-Catholic immigrants settled this stretch of the North Side in the 1830s, farming what had been swampland into potato and cabbage fields, which is where the old nickname "the Cabbage Patch" comes from.
This year, OTMRA is holding its pre-Oktoberfest member networking event at the House of Glunz, the wine shop at 1206 N Wells that Louis Glunz Sr. founded in 1888 after emigrating from Westphalia. It's recognized as the oldest family-owned wine shop in the country still run by the same family, and it predates almost everything else currently open on that block by more than a century. That's not a coincidence of scheduling. It's the organization anchoring a two-year-old festival to the one business on the street that actually earns the German heritage the event is named for.
The rest of the corridor tells a similar story if you know where to look. The Fudge Pot, at 1532 N Wells, has been making fudge on-site since 1963, and its owner, James Dattalo, currently serves as OTMRA's president. Kamehachi, a few doors down, was Chicago's first sushi restaurant and is still run by three generations of women in the same family. None of these are the flashiest names on the street, but they're the ones that make Old Town's version of Oktoberfest feel less like a rented theme and more like a neighborhood remembering what it already was.
"We are thrilled to be hosting the inaugural Old Town Oktoberfest," Marcy Huttas, OTMRA's executive director, said when the festival launched last year, with a $5 suggested gate donation set up to help fund it as a recurring event.
Context matters here because Old Town isn't the only Oktoberfest competing for a Chicago weekend this fall. Fulton Market is running its own version, a six-week ticketed production from Oktoberfest Nation that pours imported Hofbräu München beer and runs from September 17 through October 26. It's a bigger operation by design, built around a paid-entry model and a beer brand rather than a neighborhood's own history.
September 18 to 20 also happens to be the single busiest Oktoberfest weekend across the wider region this year, with festivals in Palatine, Elk Grove, and Mount Prospect all running at the same time as Old Town's. Old Town's version doesn't try to out-scale any of them. It's donation-based, walkable from three CTA lines, and staffed by the same merchants who run the shops you'd pass on any other Saturday. That's the actual difference between a neighborhood hosting its own history and a city renting a German theme for six weeks.
If you haven't walked Wells Street in a few months, a couple of things shifted since last year's festival that are worth knowing before you go this time. FARE, the healthy bowl and coffee concept that got its start as a downtown food-hall counter, is opening its own storefront at 868 N Wells, on the west side of the street near Layla & Ringo's Cafe and Petite Edith. It's a homecoming of sorts for the brand, which is finally getting a full location on the same street where its founders first worked in Chicago restaurants together.
Down the block, SHŌ Omakase, which opened in August 2025, picked up a 2026 James Beard semifinalist nod for Best Chef in the Great Lakes region, a fast turnaround for a restaurant barely a year old. It's the kind of addition that sits comfortably next to the century-old businesses without erasing them, which is more or less the pattern of the whole street right now: new openings filling in gaps rather than replacing anchors.
Public transit gets you there without needing to think about parking. The Red Line stops at Division, the Brown Line at Sedgwick, and the Blue Line at Clybourn, each an easy walk to the festival grounds, and buses along North Avenue, Division, Clark, and LaSalle also reach the area directly. The gate donation is suggested, not required, and the festival wraps into the rest of Wells Street once the main stage winds down each night, with OTMRA encouraging attendees to keep the evening going at the shops and restaurants that back the event in the first place.
None of this makes Old Town a bigger neighborhood than it was last September. It makes it a neighborhood that's figured out how to turn its own history into a weekend, rather than importing someone else's. That's a small distinction, but it's the one that separates an event with staying power from one that fades after its second year.
If you're weighing what a fall like this looks like from the inside, whether it's your first September in Old Town or your twentieth, Nancy Tassone knows this street block by block. Let's Connect.
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