Fall in Hubbard Woods: A Resident's Read on a Transition Year

Hubbard Woods is the quieter half of Winnetka's downtown, the stretch of Green Bay Road you walk when you want a leisurely errand instead of a scheduled one. This fall, the district is doing something it rarely does. It is changing in visible ways while still looking, on a Saturday morning, like the version longtime residents already know. That gap is the whole point of this post.

The short version: between the Hotel Chocolat arrival in April, Avli's expansion in March, the Tower Court proposal now working through Design Review, and the Village's Hubbard Woods streetscape study, the next twelve to eighteen months will alter how the northern business district reads. The fall of 2026 is the last season it will feel this familiar. Here is how to use it.

Two storefronts that already reset the block

The most concrete change on Green Bay Road this year is at 912 Green Bay. British chocolatier Hotel Chocolat replaced Lana Jewelry at 912 Green Bay Road and opened at 11 a.m. on Saturday, April 4, offering tastings, drinking chocolate, a portrait artist and a gift for the first 75 guests. Lana Bramlette had opened her line at the Hubbard Woods location in 2023 and is moving the store to Oak Brook. Hotel Chocolat was founded in 2004, expanded to the United States with a Chicago location in 2025, and the Winnetka shop is its fifth across Chicagoland. If you have not been in, the drinking chocolate is the item to try in October when the temperature drops. It is also a category that did not exist in the district a year ago.

Two blocks south, the other change is at Avli. More than 16 years after first opening in Winnetka, Avli is unveiling its largest transformation yet: a redesigned menu, new chef and large-scale expansion at its Winnetka location. The restaurant now occupies half of Winnetka's Laundry building, adding 2,400 square feet, with roughly 1,600 square feet of that going to a new lounge and another 800 to additional front-room dining. Chef Jorge Angulo has rebuilt the menu around mezedes, and the fish comes from the Ionian Sea, with the cheeses, roasted peppers, and olive oil imported directly from Greece. The lounge is the part worth planning around. Winnetka has almost no rooms designed for sitting for two hours with small plates and a drink. Now it has one, and it is walkable from the Hubbard Woods Metra platform.

The First Friday cadence, and why September's matters more this year

The Hubbard Woods Design District runs First Fridays through the fall. The next one is September 11, 2026. The format is after-hours shopping with live art and light hospitality, and the participating merchant list is the useful thing to keep, because it is also the roster of businesses that will be most affected if the Tower Court proposal advances. Recent First Friday rosters have included Benvenuti and Stein, Byrne Corazza Studio, heARTstudio, Mary Jo O'Gara Fine Art, Casa Spazio, Material Possessions, Robin Thomas Design, Redefined Decor, Wellyhaus, Bedside Manor, Randoons, Vivid Art Gallery, ESQ, Aqualta, Mattie M, Momsy's Cafe, Doyle Opticians, Got?Art Gallery, Winnetka Art Gallery, and Styles & Smiles.

Two things about that list. First, it is dense for a district this size. Second, several of these are the kind of independent design and gallery tenants that new mixed-use construction rarely reproduces. Walking First Friday this fall is not sentimental. It is the most efficient way to see who is actually still on the block, before the next round of retail turnover.

What Tower Court would change

The other reason this fall reads differently: a large redevelopment is moving through Village review at the same time the streetscape is being restudied. The development team behind One Winnetka is proposing to raze several buildings in Winnetka's Hubbard Woods Business District to make way for a new four-story mixed-use development along a prominent part of Green Bay Road, with a third Design Review Board hearing set for July 16. Known in submittal documents as Tower Court Condominiums, the plan first surfaced in public meetings in late October of last year, and the building would include nearly 16,000 square feet of retail space and upwards of a dozen residential units. Design Review Board commissioners during their initial May 21 review expressed concern about the "height, scale, and compatibility with the surrounding buildings," as well as hesitations about the building's "urban" appearance in an intimate downtown setting.

Whether Tower Court is approved in its current form, revised, or slowed, it is a real signal. It is the same development group behind One Winnetka, the mixed-use project rising at Elm and Lincoln on the other side of the village, where the remaining three floors above street level will hold up to 59 residential units and the first-floor retail space is sold out. Two four-story mixed-use buildings, one already under construction and one in review, is a scale of change Winnetka has not seen at once in a long time. The Elm Street version is committed. The Hubbard Woods version is still being argued.

Underneath both, the Village is separately studying the district's public right-of-way. Winnetka has commenced a streetscape planning effort for the Hubbard Woods Business District and is planning improvements within the public right-of-way, similar to those made in the Elm Street Business District. The Elm Street precedent matters. If you have walked Elm since its streetscape, you know how much a sidewalk redesign can change the feel of a block that otherwise kept the same tenants. Hubbard Woods is a candidate for the same treatment.

The residents' fall map

Here is a way to use the district before any of that lands. This is a Saturday, roughly ordered.

1. Morning at the Winnetka-Northfield-Glencoe Chamber Farmers' Market. It runs at the 754 Elm lot in the Elm Street District. Walk it, then take Green Bay Road north.
2. Coffee and pastry in Hubbard Woods. Towne & Oak on the Hubbard Woods side is the chef-driven café for breakfast, lunch, and coffee, with catering capacity that quietly handles a lot of the neighborhood's private events.
3. A stop at Hubbard Woods Park. The Splash Pad is open Memorial Day weekend through October 1 from 8 a.m. to 8 p.m., and bocce balls are available to use for free at Green Bay Cycles; inquire inside the store. The October 1 date is the one to circle. After that, the pad is closed until Memorial Day.
4. Design district browsing. The First Friday merchant list doubles as a daytime map. Benvenuti and Stein, Material Possessions, Casa Spazio, and Wellyhaus each carry the kind of inventory people usually drive to the West Loop for.
5. Drinking chocolate or a truffle flight at Hotel Chocolat. New enough that the staff is still walking guests through the menu, which is the right time to go.
6. Early dinner south of the tracks. Hubbard Woods on the north end has become the strongest concentration for a leisurely meal, with Tocco at 985 Green Bay as Bruno Abate's authentic Italian room, a short walk from Grateful Bites Pizza Shoppe at 899 Green Bay, the brick-and-mortar spin-off from Grateful Bites Catering doing wood-fired pizza.
7. A late seat at Avli's new lounge. The mezedes menu is built for it.

That is a full day inside a half-mile radius, with almost no driving between stops. It is also, functionally, the district's argument for itself.

Two smaller items residents tend to miss

A pair of things worth flagging while you are in the area this fall. Items from the 1976 time capsule, opened on July 3, are now on display at the Winnetka Historical Society at 411 Linden Street on Tuesdays and Thursdays from 1 to 4 p.m. It is a short, free stop that is only interesting in this specific window.

The second is a Sunday routine that pairs well with Hubbard Woods. Fuelfed's Coffee and Classics meet returns Sunday, July 26, 2026, from 9 to 11 a.m. at 111 North Green Bay Road, a two-hour window of vintage and enthusiast cars in an open lot, low-key, and free. The season is limited. If you have not walked one, this fall is a reasonable time to start.

Why the timing matters

The through-line across all of this is that Hubbard Woods is in a rare posture. The tenant mix on Green Bay Road is currently unusually strong for a village this size, the district still walks the way it did five years ago, and two structural changes, Tower Court and the streetscape study, are both moving in parallel behind the scenes. None of the current tenants are going anywhere immediately. But the composition of the block a few years from now will not be identical to the composition today. Residents who treat this fall as a normal season will get a normal fall. Residents who treat it as a transition year will use the district harder, notice more, and be less surprised the next time they walk past 912 Green Bay and something else is in the window.

If your interest in Hubbard Woods eventually extends beyond the storefronts to the homes behind them, Jena Radnay works this village and the surrounding Winnetka blocks every week. Request a Private Consultation.