Winnetka: Open for Business!

That's the call we want to hear from Village Hall: an invitation welcoming entrepreneurs, economic development, and creative partnerships—and even actively seeking them out.

It would be a cultural shift in how the Village approaches growth, and it isn't optional to Winnetka's long-term fiscal health.

The consequences of a near hostility to progress are visible everywhere – manifesting as a growing backlog of infrastructure projects we delay, underfund, or simply cannot afford. If we were a student, OTW would give our Village an "F":

• Tower Pier - shuttered, and needing $$$$$ to fix
• The $100 million East Side Storm Sewer project – Needed, yet no funding yet $$$$$ going to consultants to tell us what we already know: We need to do this.
• The long-degrading Hubbard Woods parking deck – sitting as an eye-sore
• The stalled Green Bay Trail improvements—planned, funded, but unrealized.

Now the Village is launching a capital improvement study … fingers crossed. Another study, which the village has made an art form out of, or will some changes really come of it. Hopefully skeptical.

The question lingers: why are we here in the first place? Do we really need another study or a different mind set?

The Real Issue Isn't Money—It's Mind Set and Approach

Village leadership may argue these assets remain in disrepair because there isn't enough money. But why isn't there?

Because Winnetka has never established a coherent approach to expanding its tax base. Resistance to modernizing downtown, revitalizing unworking or underused spaces, and diversifying housing options has real financial consequences. These aren't abstract debates—they directly affect the Village's bottom line.

This is a mind set. How about setting a revenue base needed to afford the Village needs and infrastructure. Work from the need back versus always saying no to development.

A Model That Worked—And Then Stopped

To be fair, Winnetka has shown what's possible.

Consider Tala Coffee. For years, a small service station garage, right at the busy intersection of Green Bay Road and Winnetka Road, sat underutilized—leased sporadically, then left idle. Eventually, the Village tried something different: it issued requests for proposals and invited entrepreneurs to reimagine the site. The process took time—nearly three years of negotiation—but the result was worth it. However, three years is ridiculous. We should do better.

Today, Tala Coffee anchors a vibrant public space in the Indian Hill neighborhood, where daily commuters can pick up a coffee, and it is a nice break for New Trier Students and community members. A great solution. Private investment revitalized the structure. A café brought energy and foot traffic. The surrounding area improved. Parking actually increased. And the Village secured long-term value through a 100-year lease.

It wasn't just a successful project. It was a blueprint. So where are the others?

Opportunity Is Everywhere

Walk through Winnetka and you'll see it: underutilized public land scattered throughout the Village. Parking lots. Small parcels. Transit-adjacent spaces. And lets not forget the street ends on the Lakefront, which private residents would love to have the opportunity to explore. Properties that currently cost money to maintain could instead generate revenue, attract investment, and enhance community life.

The opportunities are not hypothetical:

• Land near the Indian Hill train station – considered as a location for reasonably priced, affordable housing
• The Hubbard Woods parking structure – would be a great 'end cap' to the north end of our community, where the design district is back in full swing and there is the Northwestern Train station to attract people along the North Shore and Downtown Chicago
• The lot adjacent to the Community House – long considered a multi use facility, potentially now to mirror One Winnetka. Imagine living there, with an all access walkway to all that the Community House has to offer for both health and creative pursuits!

And many more. Yet year after year, the same issues dominate the conversation—aging infrastructure, flooding, the lakefront, the Post Office site. Each is treated as a separate problem. Each is studied, debated, delayed. Each becomes more expensive.

We need to work back from what revenue is needed and find a path so residents have the services and infrastructure expected. Step back, and a pattern emerges. We just need to take a look at what our friendly neighbor Wilmette is doing by having a developer come in to purchase/develop the Metra land right in the heart of the town. Great idea, easily repeatable at two of our three train stations!

The problem isn't a lack of solutions. It's a lack of an overarching mind set and game plan to optimize the parcels and bring a 'win-win' solution to both community needs and Village revenue.

When Collaboration Works

Winnetka has already proven that a different approach works. Consider the partnership between the Village and the Park District: one needed stormwater storage; the other wanted a golf course. The result delivered both.

On a larger scale, the same mindset helped solve one of Winnetka's oldest challenges: flooding. For decades, the Village approached the issue alone, pursuing expensive and incomplete solutions. Then came a shift in thinking: What if the answer wasn't confined to Village boundaries? What if it involved the Park District, the schools, and the County?

The result: a coordinated system that detains 140 acre-feet of stormwater across multiple properties. The impact was substantial:

• A more effective solution
• Roughly $12 million in savings
• A redesigned golf course that doubles as stormwater infrastructure
• National recognition for environmental innovation

This is what happens when Winnetka stops going it alone, and works together.

The Cost of Going It Alone

Now consider a smaller—but equally revealing—example.

Last year, the Village spent $320,000 to replace just 65 feet of pipe at Elder Lane. Sixty-five feet. At the same time, the Park District had offered to fully fund the relocation of that storm sewer. That offer has been on the table since September 2024. The Village declined.

It would be almost laughable if it weren't so telling. It reflects a deeper issue: an institutional reluctance to collaborate—even when collaboration clearly serves the Village's interest.

A Playbook Hiding in Plain Sight

The path forward isn't complicated. We've already seen it work. Public assets can be reimagined. Parking lots can become mixed-use spaces. Transit areas can be revitalized. Small parcels can return to the tax rolls. Developers and entrepreneurs can be invited—not feared—to bring ideas forward.

If proposals fall short, nothing changes. But if they succeed, the entire community benefits.

Winnetka doesn't need a new strategy. It needs to apply the one it already has—consistently, confidently, and at scale.

Because the real question isn't whether Winnetka can afford to evolve. It's whether it can afford not to.

\# \# \#

Our Town Winnetka is seeking your help and advocacy!

Beyond these frequent emails, we are now seeking residents to join our team. We are seeking:

• Residents who are willing to go to our various Village Council / Historic Preservation / Zoning Board of Approvals / Winnetka Park District meetings to speak their minds for their fellow citizens -- and share their observations back to OTW.
• Residents who are open to hosting a coffee at their home to discuss the key issues with fellow residents and bring the key insights & summary points back to OTW.
• Have a story that is worth sharing, via our newsletter, where a resident needs help navigating local permitting processes, whether your personal residence or local business.

If interested, please click on the link to submit your interest to the page on our website.

Founded in 2024 by Ed Harney and Ian Larkin,* Our Town Winnetka (OTW) was organized with a simple principle: We need to be more inclusive and transparent in our Winnetka Caucus and Government Process.

*Ian Larkin, given his 2025 WCC Chairmanship, has resigned from OTW.

Our Promise to You

Winnetka, simplified. With clarity, transparency, and a balanced point of view.