Hubbard Woods' Last Two First Fridays of 2026, and What's Happening a Few Doors Down
There's a particular version of Hubbard Woods that shows up on the first Friday of the month, from April through October. The lights stay on late at Casa Spazio and Robin Thomas Design. Doyle Opticians and Momsy's Cafe leave their doors open past closing time. Someone's pouring wine near the gallery windows at Winnetka Art Gallery, and if you time it right, there's live painting happening in plain view of the sidewalk. It's the kind of evening that makes Green Bay Road between Tower Road and Scott Avenue feel less like a commercial strip and more like a block party that happens to sell furniture and eyewear.
This year, that run has two dates left. September 11 is the next one. October 2 closes out the 2026 season with the district's Art Walk, the calendar's traditional finale. If you've been to even one First Friday this year, you know the format: 4 to 7pm, after-hours shopping, live music, small bites, the merchants who make up the Hubbard Woods Design District doing what they do every month.
What's easy to miss, walking that same stretch with a glass of something in hand, is that the buildings on either side of the party are the subject of a much slower, much more contested conversation happening in Village Hall.
The Hubbard Woods Design District occupies a compact run of Green Bay Road, and the businesses who host First Friday, the galleries, the boutiques, the design studios, aren't the same businesses currently facing a demolition proposal one block over. But they're neighbors on the same three-block stretch, and that proximity matters more than most people walking through on a Friday evening realize.
A developer's plan known as Tower Court Condominiums would demolish four buildings to make way for a new four-story mixed-use structure:
In their place would rise a building with just under 16,000 square feet of ground-floor commercial space and 14 residential condominiums above it, plus underground parking. None of that is speculative. It's what's in the submitted plans, and it's what Winnetka's Design Review Board has been picking apart since the proposal first surfaced at a Village Council preliminary review in late October 2025.
The project keeps running into the same two objections. The first is height. Winnetka caps new construction in this corridor at 45 feet, and the current proposal asks for 62, a 17-foot variance in a village that treats its height limit like load-bearing policy. Trustee Kirk Albinson made the stakes plain at last fall's council review, arguing that granting the variance would set a precedent for every developer who comes after this one. The second objection is parking. The village's own math puts the minimum requirement at 61 spaces for a building this size, split between residential and commercial use. The proposal on the table offers 55, a six-space shortfall in a district where finding a spot on a Friday night already takes some patience.
The Design Review Board's chair, Katie Moor, summed up where things stood as of this summer in a comment that captures the whole tension of the project:
"This just to me, as it stands right now, still, even with the changes, which are terrific relative to version one, doesn't feel like it fits it."
That was from the board's second review, held June 18, 2026. A third hearing was scheduled for mid-July. Even once the Design Review Board reaches a verdict, the project still has to clear Winnetka's Planned Development Commission, with the Village Council holding final say after that. In other words, nothing about those four storefronts is settled, and nothing about them will be settled quickly. If you walk past Rebel House or Bella Bleu Bridal on your way to the September 11 First Friday, they're exactly as open for business as they were last month.
The redevelopment fight isn't the only thing in motion on this stretch. Winnetka's own spring 2026 village report noted that the Council spent time in January discussing the Hubbard Woods parking deck itself, covering structural repairs, surface protection, future EV charging capacity, and signage. That's a separate track from the Tower Court proposal, and it's a smaller one, but it lands on the same three blocks in the same year. One conversation is about whether to tear down and rebuild. The other is about whether to patch and maintain what's already there. Both are unfolding while the design district keeps running its monthly calendar as if none of it were happening, because from the merchants' side, none of it is happening yet.
That's the real texture of Hubbard Woods this fall. It's not a business district bracing for imminent change. It's a business district hosting its usual party while a separate, much slower process plays out a few storefronts away, one that could eventually change the width of the sidewalk you're standing on, but hasn't yet, and won't for a while.
If you're planning to make it to the September 11 event or the October 2 Art Walk, nothing about the experience changes. The merchants who run First Friday, the ones with the wine and the live music and the extended hours, aren't part of the demolition footprint. Aqualta, Mattie M, Redefined Decor, Bedside Manor, Wellyhaus, heARTstudio, and the rest of the roster that shows up on Nextdoor every month are hosting exactly the kind of evening they've hosted since the series started.
But if you find yourself walking past the storefronts at 901 through 913 Green Bay Road, or past Europa Motors on Tower Road, you're walking past the specific addresses named in a proposal that's been through multiple Design Review Board hearings without a green light. Whatever you think about the height variance or the parking numbers, it's worth knowing which buildings are actually in play and which ones aren't, especially in a district small enough that every storefront matters to the character of the whole block.
The Village of Winnetka posts Design Review Board and Village Council agendas publicly, and The Record North Shore has been the most consistent source tracking the Tower Court story hearing by hearing. Either one is a better way to follow what happens next than guessing from the sidewalk.
For now, the calendar hasn't changed. Two First Fridays left, one regular, one closing out the season with Art Walk. The buildings on either side of the party are still standing, still occupied, and still very much in the middle of a decision nobody in the village has made yet.
If you're the kind of Winnetka resident who tracks what's actually happening on your own streets, not just what shows up on a flyer, that's the kind of local read we try to bring to every corner of the North Shore. If a question about Hubbard Woods, or any other pocket of the neighborhood, ever turns into a real estate question, The Keki Cannon Team is a call away. Let's Connect.
Highland Park
What Highland Park homeowners and buyers should know about ravine properties, setbacks, maintenance, and the rules that protect them.
Glenview
New restaurants, new residents and a packed September calendar are changing the feel of downtown Glenview.
Our deep local roots create a complete knowledge base—covering schools, public amenities, and local culture—allowing us to meet every client's needs with absolute precision.
Get In Touch With Our Team To Learn More
