On September 11, the Hubbard Woods Design District opens its doors after hours for First Friday, the monthly art walk that has run every May through October for years along Green Bay Road. Merchants stay open late, a few galleries put artists to work with easels in the windows, and this year there's a new stop for anyone who wants a hot chocolate flight to go with the gallery hopping. It reads like a routine. It is a routine. But this particular First Friday falls in the middle of a Design Review Board process that could change which storefronts are even standing the next time the district throws open its doors in October.
That's not a coincidence worth glossing over. Three of the design studios that give the Hubbard Woods Design District its name sit on parcels currently up for demolition under a proposal called Tower Court Condominiums, working its way through Village review this summer. The people hosting First Friday and the people whose buildings are on a redevelopment plan are, in several cases, the same people.
What First Friday Actually Is
The Hubbard Woods Design District runs along Green Bay Road between Tower Road and Scott Avenue, a stretch of classic Tudor storefronts that the district's own materials describe as over a mile of walkable shopping. The monthly First Friday series brings together the neighborhood's design studios, galleries, and boutiques for an evening of after-hours shopping, live painting demonstrations, and music, typically from 4 to 7 p.m. September's edition is the second to last of the season. October wraps things up with an Art Walk before the district goes quiet for the winter.
The merchant roster reads like a small design fair: Casa Spazio, Robin Thomas Design, Material Possessions, Mattie M, Momsy's Café, Doyle Opticians, Vivid Art Gallery, Benvenuti and Stein, heARTstudio, Bedside Manor, and Winnetka Art Gallery, among others. The district's own design directory also names Alexandra Kaehler Design, Munder-Skiles, and Rebel House Design as members, a detail that matters more than it sounds like it should.
The food and drink side of the block has filled in recently too. Hotel Chocolat, the British chocolatier, opened at 912 Green Bay Road on April 4, taking over the space that Lana Jewelry vacated when its owner relocated the business to Oak Brook. Lana Jewelry had only opened that Hubbard Woods location in 2023, which means the storefront has already turned over once in the last three years. A short walk away, Tocco serves Bruno Abate's Italian menu, Grateful Bites Pizza Shoppe does wood-fired pies at 899 Green Bay as the brick-and-mortar arm of Grateful Bites Catering, and Towne & Oak handles breakfast, lunch, and coffee along with enough catering capacity to cover a lot of the neighborhood's private events. Hubbard Woods has quietly become the North Shore's steadiest concentration for an evening meal that doesn't require a drive.
The Four Parcels
Here's where the story stops being purely a food and shopping update. A development team led by OKW Architects, the same firm behind the One Winnetka project under construction at Lincoln and Elm, has proposed a four-story, mixed-use building on four Hubbard Woods parcels. The plan first went to Village Council in a preliminary review in late October 2025, then moved to formal Design Review Board hearings this year, with sessions on May 21 and June 18, and a third scheduled for July 16.
The proposal, submitted under the name Tower Court Condominiums, would demolish the following:
| Address | Current Tenant(s) | Status Under Proposal |
|---|---|---|
| 901-905 Green Bay Road | Rebel House Design, Red Spade Landscape Design | Slated for demolition |
| 907-909 Green Bay Road | Bella Bleu Bridal, Alexandra Kaehler Design | Slated for demolition |
| 911-913 Green Bay Road | Munder-Skiles, one residence | Slated for demolition |
| 1007-1011 Tower Road | Europa Motors | Slated for demolition |
In their place, the plan calls for roughly 14 residential condominiums above just under 16,000 square feet of ground-floor commercial space, with 55 parking spots, nine at street level and 46 underground. The original version of the plan asked for a height variance, 62 feet against Winnetka's 45-foot limit for the corridor, a request that drew pointed pushback from Trustee Kirk Albinson, who said granting it would set a precedent for every future developer on Green Bay Road.
By the June 18 Design Review Board session, the team had revised the design to reduce its footprint on the streetscape. The board's chair, Katie Moor, called the update a real improvement over the first version but still wasn't ready to sign off. Her comments, reported by The Record North Shore, get at exactly the tension the neighborhood is sitting with right now:
"We just want to do it the right way and make sure we're preserving and enhancing what's there."
Nothing here is settled. The proposal still needs to clear the Planned Development Commission and, ultimately, a Village Council vote, and there's no announced timeline for either. But it means anyone walking Green Bay Road for First Friday this month is walking through a stretch of the district where roughly a quarter of its parcels are actively under review for a project that would remove the buildings entirely.
The Parking Question Nobody's Waiting To Ask
The redevelopment debate isn't happening in isolation from the district's other headache: parking. Village trustees spent part of a January 2026 meeting on the condition of the Hubbard Woods parking deck, covering structural repairs, waterproofing wear, and the possibility of adding EV charging. Separately, the Village has been running a Phase 1 streetscape study for the district, with a public meeting held June 15 to gather feedback on roadway design and how to better connect the existing public garage to the merchants who rely on it.
That's the backdrop against which the Tower Court proposal's 55 new spaces have to be evaluated. The existing deck is already old enough to need structural attention. Whether a new development's parking count actually eases pressure on a district that's simultaneously trying to fix what it has is a question the Design Review Board, the Planned Development Commission, and eventually the Village Council will have to work through before anyone breaks ground.
Where That Leaves September 11
None of this changes what First Friday looks like this month. The galleries will be open, Hotel Chocolat will likely still have a line for its hot chocolate flights, and Grateful Bites will still be pulling pizzas out of a wood-fired oven a few doors down from Tocco. But if you're a regular at any of the studios named on that demolition list, this fall's First Fridays carry a little more weight than a typical after-hours shopping night. The design district that gives Hubbard Woods its identity is, in a real sense, mid-decision about its own shape.
Residents who care about how this corner of the North Shore keeps its character while it grows have a genuine reason to follow the Design Review Board's next moves, not because a home purchase is on the table, but because the outcome will determine what's actually standing here the next time October's Art Walk rolls around.
If you're watching how these North Shore neighborhoods evolve and want a local read on what it means for property values, presentation, or timing a move, Nicole Fabiano has spent 25 years tracking exactly this kind of change across Lake Forest, Lake Bluff, and the wider North Shore. Reach out to request a complimentary home valuation and get a grounded, neighborhood-level perspective before you make your next move.
