"Ashland is a barrier for biking and walking. The highway is a barrier, and the railroad is a barrier," says Ben Helphand, co-founder of Friends of the Bloomingdale Trail, describing the stretch where the 606 simply stops.
If you walk or bike the trail regularly, you already know this without needing anyone to explain it. You ride the smooth, elevated 2.7 miles from Ridgeway to Ashland, past the murals and the overlooks and the trailside plantings, and then the path ends at Walsh Park and dumps you onto the ground, into the tangle of the Cortland and Ashland intersection, to fight your way toward Elston on foot or by bike like everyone else in a car. It's the one part of the 606 that doesn't feel designed. It feels like it ran out of budget.
That's not far from the truth. And this is the fall that gap finally starts closing, on a timeline that's worth understanding before you plan around it.
A Decade-Long Half-Mile
The Bloomingdale Trail opened in June 2015, built on the old elevated Bloomingdale Line that had carried freight since 1873. From the beginning, the plan was for the trail to eventually cross Ashland, duck under the Kennedy Expressway and the Union Pacific tracks, and connect to Elston Avenue, close enough to eventually reach Lincoln Yards and the river. The Chicago Department of Transportation didn't unveil actual preliminary designs for that extension until August 2023, eight years after the rest of the trail was already drawing more than a million users a year.
Since then, the completion date has already slipped once. At the 2023 public meeting, CDOT planner Soliman Khudeira told residents construction could start in late 2025 and wrap by the end of 2026. By January 2025, CDOT had pushed construction back to the end of 2026, with the whole extension now expected to open in late 2027. That's the timeline that still stands: if you're new to the neighborhood and just now hearing about "the 606 extension," you're not behind. Nobody's ridden it yet, and nobody will for at least another year.
Why Sterling Bay Isn't Just Paying For It
Here's the part that surprises most people who assume Lincoln Yards is bankrolling this. It isn't, and the reason is a boundary line on a map.
When the city approved Lincoln Yards in 2019, it created the Cortland and Chicago River tax increment financing district, a $1.3 billion pot meant to reimburse developer Sterling Bay for infrastructure that benefits the megaproject. The trail extension would obviously benefit Lincoln Yards. But the physical footprint of the extension, the bridge over Ashland, the underpass beneath the expressway and rail tracks, sits just outside that TIF district's boundary. So the fund built specifically to pay for Lincoln Yards infrastructure can't legally touch the one piece of infrastructure everyone assumes it's already covering.
Sterling Bay did put in $750,000 for the first planning phase. Beyond that, the city has had to piece together funding from federal, state, county and city sources for a project estimated at $30 to $40 million. U.S. Rep. Mike Quigley secured roughly $1.4 million through a congressional earmark, enough to cover about half of the detailed engineering phase. As of CDOT's last public update on the project, in January 2025, the remaining balance was still being identified. That search for money, not construction difficulty, is the real reason a project that could theoretically be built in under two years has taken more than a decade to leave the planning stage.
What This Means For How You Use The Trail Right Now
Nothing changes for your commute or your evening ride this month. The eastern terminus is still Walsh Park, and the Cortland and Ashland intersection is still the same crossing it's always been. As of CDOT's last public statement on the project, the department described itself as "wrapping up" preliminary engineering with a consultant already selected for final design, which tells you this has been a project moving through paperwork, not steel. Construction isn't expected to break ground until around the end of this year at the earliest, per that same timeline.
What's worth knowing is that you're using the trail in its last extended stretch as an unfinished sentence. Once work does start near Walsh Park, expect the kind of disruption that comes with any bridge-over-a-major-street project: fencing, detours, maybe a temporary rerouting of the Ashland crossing itself. None of that is scheduled yet. But it's close enough now that it's worth checking CDOT's project updates before you assume the trail will look the same a year from now.
The Middle Of The Trail Isn't Waiting Around
While the eastern end sits in funding limbo, the rest of the 606 had an active year. Four new murals went up this spring, including one at the Milwaukee Avenue trail entrance by artist Ramiro Huizar, inspired by his own kids learning to ride bikes and scooters, and a "Welcome to Wicker Park" style postcard mural by Andrew Jesernig near Milwaukee and Honore, built around local landmarks like the Wicker Park fountain and the Blue Line. Neither is temporary. Both join permanent works already along the trail, including Luftwerk's "Turning Sky," a lighting installation on the Milwaukee Avenue Bridge that shifts color with the day's actual weather, and Jenny Kendler's "Birds Watching," a forty-foot line of reflective bird's eyes between Kimball and St. Louis representing species threatened by climate change.
Below the trail, the Wicker Park Farmers Market is in its 26th season, running Sundays from 8 a.m. to 2 p.m. through October 25 at 1425 N. Damen Avenue, with yoga and Pilates classes most weeks and monthly dog training sessions at the Wicker Park Dog Park through a partnership with Canine Crews. And a few steps off the Milwaukee Avenue access point, inside the Kimball Arts Center, Dayglow was named the best coffee shop in Illinois by Food & Wine, which is either a nice bit of trivia or your new excuse to get off the trail one exit earlier than usual.
Here's the split in one place:
| On the trail right now | Still waiting on funding |
|---|---|
| Four new murals (spring 2026), including work at Milwaukee/Honore | Ashland-to-Elston extension, still in final design |
| Permanent Turning Sky light installation at Milwaukee Ave Bridge | Construction start pushed to end of 2026 |
| Wicker Park Farmers Market, 26th season through Oct. 25 | Full completion pushed to late 2027 |
| Dayglow at Kimball Arts Center, Food & Wine's top IL coffee shop | Remaining ~$30-40M construction budget still being sourced |
What's Actually Worth Doing Before The Season Turns
- Catch the Wicker Park Farmers Market before it closes for the year on October 25. The added produce vendors this season mean more options than in past years, and the weekly programming rotates.
- Walk the Milwaukee Avenue entrance slowly enough to actually see the new murals. Huizar's piece rewards a second look, especially at dusk when the Turning Sky lighting a block away starts to shift.
- Detour into the Kimball Arts Center for Dayglow if you haven't. It's easy to pass without noticing from the trail itself.
- If you're a regular rider heading east toward Ashland, keep an eye on CDOT's Bloomingdale Trail extension page. The "construction expected to begin" language means this is the season to watch for the first signs of it, not necessarily the season it arrives.
The Trail You Have Left
The 606 has always been described as finished, a completed 2.7-mile amenity that transformed an old rail line into one of the city's most-used parks. That's true for the middle of it. But the eastern half mile has been a work in progress since before most current Bucktown and Wicker Park residents moved in, and the funding story behind that delay, a TIF boundary that excludes the one project everyone assumed it covered, says as much about how these things actually get built in Chicago as any ribbon-cutting would.
For now, the trail you ride today is close to the trail you'll ride next fall. The version after that, the one that finally clears Ashland without a fight, is still a year away. Knowing that difference, and knowing why it took this long, is the kind of thing you only pick up by paying attention to a neighborhood you already live in.
If you're curious what else is shifting in Bucktown and Wicker Park this season, from new restaurant openings to how the neighborhood's older and newer construction sit side by side, our Bucktown/Wicker Park neighborhood guide stays current with it. And if a conversation about the neighborhood ever turns into a conversation about buying or selling here, that's where Cadey O'Leary Collection comes in. Work with Cadey. Start the conversation.
