The Bloomingdale Trail Just Turned Eleven. Here's What Actually Showed Up in Wicker Park.

Walk the trail access at Damen this month and you'll notice the retaining wall near Milwaukee and Honore isn't blank anymore. A few blocks south on Division, there's a walk-up window drawing a line next to the Original Rainbow Cone that wasn't there over the summer. Neither of these things got a ribbon cutting. Both are more evidence of where Wicker Park actually changed this year than anything the city put its name on.

The Bloomingdale Trail opened to the public on June 6, 2015, which means it crossed its eleventh year this past June, not its tenth. The tenth anniversary came and went in 2025, and it produced a modest, community-run wave of programming rather than a single big event: a trail cookbook, a print series sold through a local gallery, and a mural initiative meant to fill in the concrete embankments that have sat mostly blank since the trail opened in 2015. A year later, the pattern holding for the anniversary is holding for the neighborhood around it too. The small, privately driven additions are already finished and in use. The large, publicly funded ones are still behind schedule.

Eleven Candles, Two Murals

Friends of the Bloomingdale Trail set out to add twelve murals along the trail's embankments as part of the tenth-anniversary programming. As of this past May, two were up. Artist Andrew Jesernig painted one near the corner of North Milwaukee Avenue and North Honore Street, and the artist known as Sentrock added "Bloom" directly across the street, both rendered in Chicago flag colors. The rest of the planned twelve are still blank wall, which means the honest way to describe the mural project right now isn't "done" but "underway, and worth checking on the next time you're near that stretch."

The pace tracks with how the whole anniversary effort has run. Bonnie Tawse compiled a trail cookbook. Gallery owner Zissou Tasseff-Elenkoff is releasing one print a month through his shop, All Star Press, with proceeds split between the artists and the trail group. It's grassroots funding moving at grassroots speed, which is not a complaint. Ben Helphand, who co-founded Friends of the Bloomingdale Trail and helped conceptualize it with city planners, put it simply after a decade of watching commuters and dog walkers take over what used to be freight tracks:

"Ten years later, I am still like, 'What the hell? This used to be a railroad.'"

The $30 Million Piece Nobody's Using Yet

Compare that grassroots pace to the trail's one true infrastructure ambition: extending the elevated path east under the Kennedy Expressway to Elston Avenue, closing the gap that currently forces trail users off the path at Walsh Park and through the Cortland and Ashland intersection to get any farther east. The Chicago Department of Transportation put the project's cost at $30 to $40 million back in 2023 and originally targeted completion by the end of 2026. In the most recent public timeline CDOT has shared, from January 2025, construction still hadn't started, funding sources were still being identified across federal, state, and local partners, and the completion date had slipped to late 2027.

That's not a knock on the city's planning process. Extending an elevated trail under an active expressway and a set of railroad tracks is a different order of project than commissioning a wall mural, and it shows in both the price tag and the timeline. But it does mean the version of Wicker Park's trail anniversary you can actually walk through today is the cheap version: two murals, a cookbook, a print series. The expensive version, the one that would let a runner go straight from Wicker Park into the Lincoln Yards development without detouring through traffic, is still a rendering and a funding search.

What Opened While You Were Walking the Dog

The ground-level turnover has moved faster than either the murals or the bridge. A few specific changes from this year:

The Buona opening is the freshest entry on that list, and it lands in a spot with its own history: a walk-up window built to evoke the neighborhood beef stands that helped make the Italian beef sandwich a Chicago staple in the first place, set down next to a Rainbow Cone location that's been a Division Street fixture for years. A few blocks over, the Chicago Pickle Eatery and Green Ape pairing on Milwaukee gave the block two new operators at once rather than one slow refill.

Not everything on Division held steady. The Yolk that anchored the corner between Damen and Wolcott for a decade closed, and a brunch operator with roots in Lakeview has been running soft openings in its place as of this past August. That's the kind of turnover that reads differently depending on how long you've lived here. A restaurant that held one corner for ten years leaving is a real changeover, not background noise, and it's worth knowing before you plan your next Sunday brunch route.

The Plaza That's Still a Rendering

There's one more project worth watching for the same reason the Elston extension is worth watching: it's been announced, it's been targeted for a date, and that date has already passed without an opening. Vienna Beef, a Chicago institution with more than 130 years behind it, is converting its longtime factory site at the confluence of Damen, Elston, and Fullerton into a public plaza with a restaurant, a factory store, and landscaped outdoor seating. The project was targeted for a mid-2026 opening. As of this past August, it hadn't landed.

It sits at the same three-neighborhood seam as the trail's own unfinished business, close enough to Bucktown and Lincoln Park that whichever direction you approach from, you're crossing an invisible border to get there. When it does open, it'll do what Wolf & Company's ramp already does on a smaller scale: turn a stretch of the trail from something you pass over into something you can actually stop at.

What This Means If You're Already Here

None of this requires a decision from you. It requires paying attention to a neighborhood that's adding pieces faster than any single roundup can capture. If you're walking the trail this week, the two finished murals near Milwaukee and Honore are worth the short detour off the main path. If you're picking a lunch spot, the Milwaukee Avenue stretch has two new options that weren't there in the spring. If you're headed to Division for ice cream, there's now a reason to grab a sandwich first.

The bigger projects, the bridge to Elston and the Vienna Beef plaza, are both still coming. Neither has a firm date you should hold anyone to. But the version of Wicker Park you can already stand in is more finished than the headlines about it suggest, and most of what changed didn't wait for a press release.

If you're curious what any of this means for property values along the trail corridor, or you're just trying to keep track of a neighborhood that keeps adding things between newsletters, Dwell Wisely Group tracks Wicker Park block by block. Schedule a free consultation whenever you're ready to talk specifics.