Downtown Western Springs Holiday Season 2026: Santa on Tower Green, Cinderella on Stage and Two New Spots Downtown
Western Springs' holiday season happens on one lawn over two weekends. Santa sits for photos on Tower Green, 914 Hillgrove Avenue, on Saturday, November 28, Sunday, November 29, Saturday, December 5 and Sunday, December 6. The first weekend has Santa and very little else. The second weekend adds Winter Wonderland, the Village tree lighting and opening weekend of the Theatre of Western Springs' Cinderella. If your calendar has room for only one holiday outing in December, that difference should decide which weekend you pick.
The Western Springs Business Association runs Photos with Santa, and families sign up for a specific day and time in advance. Each day's form lists the same terms:
Each day also has its own sponsor, and all four are local dental and orthodontic practices.
| Date | Day | Photo sponsor | What else is on the green |
|---|---|---|---|
| November 28 | Saturday | Petty and Dragstrem Orthodontics | Santa photos |
| November 29 | Sunday | Schroyer Dental | Santa photos |
| December 5 | Saturday | Spring Orthodontics | Winter Wonderland, 12 to 5 p.m., and the Village tree lighting |
| December 6 | Sunday | Dr. Brian Wooley, DMD | Santa photos |
The photo setup, the price and the address are the same all four days. Only the third day also hosts a festival. On the weekend after Thanksgiving, Santa is the only thing happening on the green. Santa photos also fill the Sunday after Winter Wonderland, which can suit a family that wants a calmer visit.
Sign-ups are on the WSBA Winter Wonderland page, and the association answers questions at [email protected].
The WSBA's 2026 calendar puts Winter Wonderland on Saturday, December 5, from noon to 5 p.m. Santa arrives on a firetruck, the Village tree is lit and Santa photos run all afternoon. The Village of Western Springs calendar also lists the event on December 5.
Recent years show how the day usually goes. In the December 2025 issue of its e-newsletter, the WSBA described Winter Wonderland on Tower Green from noon to 5 p.m. Santa arrived by firetruck at 12:30, the afternoon included a petting zoo, entertainers and free hot chocolate, and the tree was lit at 5 p.m. The 2024 event, held on December 7, used the same 12:30 arrival and 5 p.m. tree lighting and added a live ice sculpture from 1 to 3 p.m. The Village's 2025 listing also put the event on Tower Green.
In recent years, then, Santa has arrived early in the afternoon and the tree has been lit at dusk, with hot chocolate and kids' activities in between. The WSBA's Winter Wonderland page is where the 2026 schedule will appear, so check it before you go.
The Winter Wonderland afternoon also matters for Santa photos. The December 5 sessions are on the same lawn at the same time as the festival. If you book that Saturday, expect your photo slot to fall inside the bigger event, and think about whether you also want to stay for the 5 p.m. tree lighting.
On Friday, December 4, the Theatre of Western Springs opens Rodgers & Hammerstein's Cinderella. The show runs through December 13 on the Lou & Nancy Schauer Mainstage Theatre. The production is part of the theatre's 98th season, and the theatre describes it as a family-friendly musical "perfect for audiences of all ages."
Because of the dates, Winter Wonderland falls on the show's first Saturday. A family could start at Tower Green at midday and spend the evening at the theatre, all within opening weekend. Families who want to keep the two apart have the second weekend, December 11 through 13, when nothing else is scheduled on Tower Green.
Tickets are sold on the theatre's Cinderella page, and the theatre lists the production as no refunds. Book once your dates are firm.
Two downtown businesses that weren't open last December are within walking distance of the tree lighting this year.
The Clever Drinker, 4354 Johnson Avenue. This wine-focused bottle shop is in the space The Opry cocktail bar used to occupy. As Patch reported in August, it was set to open at noon on Saturday, August 29. The owners, Western Springs residents Aron Dorner and Alex Corral, told Patch they would start with retail sales and add a small by-the-glass program later. The by-the-glass program has since started. The shop's website now advertises a rotating pour menu alongside bottles to take home. It also says the business "began in London and found its new home right here in Western Springs." The website lists hours Tuesday through Saturday, with the shop closed on Mondays. This is its first holiday season. In December, that means a downtown spot for a glass of wine after the tree lighting or a place to pick up a hostess gift.
Alano Ristorante, 821 Burlington Avenue. This Italian restaurant is going into the former Salerno's Pizzeria space. Salerno's closed in January. As Patch reported on October 22, owner Chris Elsey said he hoped to open Alano on November 20 "or maybe sooner." Elsey also owns the Hillgrove Tap locations in Western Springs and Tinley Park. On his liquor license application, he described Alano as an "elegant Italian restaurant" with an estimated cost of $30 to $45 per person, drinks included. The menu he outlined includes appetizers, salads, pastas, pizza, fish, chicken and steaks, plus a bar with specialty spirits, classic cocktails, wine and beer. The target date falls in the week before Santa's first weekend on Tower Green, so check Alano's website before planning a Winter Wonderland dinner around it.
Both new businesses are a short walk from the Water Tower. Last winter, an evening that started at the tree lighting had fewer new places to continue downtown.
Once the decorations come down, the Village collects old light strings. From November 16, 2026 through January 31, 2027, drop-off points for holiday light recycling are at Village Hall, Village Ace Hardware and Thomas Ford Memorial Library, according to the Village calendar. If a strand burns out while you're decorating in late November, you can drop it off on a hardware run or a library visit long before the tree lighting.
Here is the season on one list:
If you're working out which Santa weekend fits your family, or you'd like ideas for where to eat downtown after the tree lighting, I'm glad to help. I'll see you on Tower Green. Anne Hodge | Let's Connect
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Anne thoroughly enjoys her profession and has a deep sense of responsibility to her clients. She understands the magnitude of selling or buying a home, and works tirelessly to make sure her client's goals are met.
