Ask a longtime Highland Park resident how long Oktoberfest has been part of the Ravinia District, and you'll probably get an answer that overstates it. The festival feels settled in now, tucked into Jens Jensen Park with a name-brand local brewery attached. It's easy to assume it's always been there.
It hasn't. For its first three years, Oktoberfest was a downtown event, staged at The Lot, the surface parking area at Central and St. Johns that the city started using for large gatherings in 2022. It only moved to the Ravinia District last year. And the reason it moved at all traces back to a single, contentious City Council meeting about a parking lot that had nothing to do with Ravinia on the surface.
The Meeting That Pushed Oktoberfest Out of Downtown
In August 2024, the Highland Park City Council spent a Committee of the Whole meeting arguing over what to do with The Lot. Staff had asked three questions: should the city keep hosting large events there, should events move to Port Clinton Square instead, and were any infrastructure upgrades worth making either way. The council split 4-3 against continuing to use The Lot for city-sponsored events, with Mayor Nancy Rotering and council members Anthony Blumberg, Kim Stone and Yumi Ross opposed. City Manager Ghida Neukirch told the council her staff would now look for new locations for events like Taste of Highland Park going forward.
Oktoberfest was one of the events that had been running at The Lot since 2022. When the council closed that door, the festival needed somewhere else to go. It landed in the Ravinia District, at Jens Jensen Park, for its fourth annual run in September 2025, produced by Life Rhythms Inc. in partnership with Steep Ravine Brewing Company and backed by the Ravinia Business District. A downtown parking lot debate is the reason a fall beer festival now happens two miles south, on a residential side street most of those council members probably weren't picturing when they cast their votes.
What's Different About the 2026 Version
This year, Oktoberfest returns to the Ravinia District for only its second time, and it's already outgrowing the footprint it used in 2025. According to the district's own 2026 announcement, the festival is expanding along Dean Avenue in addition to its usual space in Jens Jensen Park. Dean Avenue runs directly past Steep Ravine Brewing Company and Ravinia Speakeasy, meaning the stein-holding contest, the hammerschlagen, and the axe throwing will now spill onto the same block where those two businesses pour drinks on a normal Friday night.
The date itself hasn't changed much. This year's Oktoberfest runs Saturday, September 26, from 4 to 8 p.m. What changed is how much of the neighborhood it now touches after just one prior year in the district.
The Rest of the 2026 Calendar, If You're Keeping Track
The Ravinia District released its full 2026 lineup this spring, and most of it moves at a steadier pace than Oktoberfest's rapid expansion.
| Event | Dates | Location |
|---|---|---|
| Ravinia Farmers Market | Wednesdays, June 3 through October 28, 7 a.m. to 1 p.m. | Jens Jensen Park |
| Food Truck Thursdays | Thursdays through early September, 4:30 p.m. to dusk | Dean Avenue and Jens Jensen Park |
| America 250 themed night | July 9 | Jens Jensen Park |
| '90s Throwback Night | August 20 | Jens Jensen Park |
| Oktoberfest | September 26, 4 to 8 p.m. | Dean Avenue and Jens Jensen Park |
| Ravinia District Candy Stroll | October 30, 3:30 to 5 p.m. | Throughout the district |
| Cookie & Cocoa Crawl | December 5, 11:30 a.m. to 1 p.m. | Jens Jensen Park |
The Farmers Market enters its 48th season this year, a number that puts Oktoberfest's two years in the district in perspective. Food Truck Thursdays adds two themed nights on top of its usual rotating truck lineup, an America 250 celebration on July 9 and a '90s Throwback Night on August 20. Those are small, low-risk additions to an event the district has already run for years. Oktoberfest, by contrast, is a transplant still figuring out how much space it needs.
Why Ravinia Could Absorb an Event Downtown Couldn't Keep
The reason Oktoberfest found a stable home in Ravinia after downtown's council fight isn't an accident of geography. The Ravinia Business District operates under Special Service Area 17, a taxing mechanism the city established in 2014 to fund marketing, events and streetscape work in the district. The annual levy is $90,000, paid by the commercial and mixed-use property owners inside the SSA boundary rather than pulled from the city's general fund. Food Truck Thursdays is coordinated by Bensidoun USA, and Music in the Park runs through Life Rhythms, with the Highland Park Community Foundation contributing on the music side.
That funding structure means the district's calendar doesn't have to survive a council vote every time a budget gets tight. The property owners who benefit from foot traffic are the ones paying for the events that generate it. Downtown's Lot never had that kind of dedicated backing, which is part of why its future became a public argument in the first place. Ravinia already had the infrastructure in place to catch an event that downtown didn't have the will to keep.
The Block Oktoberfest Is Moving Into
Dean Avenue and the surrounding stretch of Roger Williams Avenue are lined with the kind of small businesses that make up the rest of the district's calendar. Steep Ravine Brewing Company and Ravinia Speakeasy sit right where the festival is expanding. Past Candy Strolls have pulled in participants like Astra Coffee Roasters, BWB Shakes, Dana Reed Designs, Maddie's Market, Piero's Pizza, Sally's Nuts, Twigs & Cotton and Viaggio, giving a sense of what a normal week on these blocks looks like before a festival tent goes up.
That's the texture worth knowing if you live nearby. Oktoberfest isn't dropping into an empty field. It's laying itself over a working strip of shops and restaurants that residents already use on an ordinary Tuesday, and this year it's using more of that strip than it did the year before.
Why This Is Worth Tracking
A festival moving neighborhoods because of a parking lot argument sounds like a small piece of city trivia. But it says something real about how Highland Park's districts differ. Downtown runs its big events through direct city sponsorship, which means they're subject to city council votes and budget politics. Ravinia runs its calendar through a self-funded special service area, which means the businesses that benefit from an event are the ones deciding whether it happens again. When downtown's political will for The Lot ran out, Ravinia's structure was ready to catch what fell through.
If you're the kind of resident who's watched Oktoberfest settle into Jens Jensen Park and assumed it had always been there, now you know it hasn't. It's a two-year-old addition to a neighborhood that was built to absorb exactly this kind of event, and this year it's already claiming more of the block than it did the first time around.
If you're curious about what else makes the Ravinia District tick, or how Highland Park's neighborhoods each carry their own character block by block, our Highland Park neighborhood guide is a good place to keep exploring. And if a conversation about this corner of the North Shore ever turns toward what a home here is actually worth, the team at Lotzof Malk Residential is always glad to Start the Conversation.
