Last December, North Center's holiday season had one main address. For two days, Dec. 13 and 14, the Holly Jolly Holiday Market filled Town Square at 4100 N. Damen with more than 20 vendors, live music, Santa and Mrs. Claus, and a trolley out to shops in North Center and Lincoln Square.
This December has no single address. There's no market. The square gets a tree lighting at 5 p.m. on one Saturday, and the shopping happens in the stores along Lincoln, Damen, Irving Park and Western across four dates between Nov. 28 and Dec. 17. The trolley is the piece of the old weekend that made it into the new one.
Five years in Town Square, then a pause
The North Center Neighbors Association ran the Holly Jolly Holiday Market for five Decembers. It grew from a single afternoon into a full weekend:
| Year | Dates | Format | What it featured |
|---|---|---|---|
| 2023, third annual | Sat., Dec. 9, noon to 6 p.m. | One day, Town Square | Gift vendors, food and drink, music and dance, Santa, the Winter Queen and Snow Angels, children's story time |
| 2024, fourth annual | Sat. and Sun., Dec. 14 and 15 | Two days, Town Square | More than 20 vendors, live entertainment, cocoa, coffee and seasonal adult beverages, Santa and Mrs. Claus on Saturday, Winter Queen and Snow Angels on Sunday |
| 2025, fifth annual | Sat. and Sun., Dec. 13 and 14 | Two days, Town Square | 20-plus vendors, live entertainment, Santa and Mrs. Claus, a trolley connecting North Center and Lincoln Square businesses |
| 2026 | Sat., Dec. 12 | Tree lighting and trolley with the Chamber | No market |
The 2023 version included vendor booths in the square. The NCNA's archived market page lists 14 merchandise vendors that year, plus food and drink vendors. The association announced the change for 2026 on its event page:
"After much thoughtful discussion, the NCNA Board has made the difficult decision not to host the Holly Jolly Holiday Market for 2026. But there is still plenty of holiday cheer coming to North Center!"
The same page says NCNA will partner with the Northcenter Chamber of Commerce on a Town Square tree lighting with a visit from Santa, plus a Holiday Trolley "connecting neighbors with local shopping, seasonal specials, and family-friendly fun," all on Saturday, Dec. 12.
The trolley is the part that carried over
In 2025 the trolley ran alongside a market of booths in the square. In 2026 the trolley is the main event, and the stores are where you get off.
The Chamber's Shop Northcenter Trolley & Tree Lighting listing has the trolley circulating through the neighborhood from noon to 6 p.m. on Saturday, Dec. 12, with hop-on, hop-off stops. The Chamber also lists gift wrapping and refreshments, and the trolley and tree lighting are both free. The tree lighting is at 5 p.m. in Town Square, and NCNA says Santa will be there.
The trolley's noon-to-6 window matches the hours of the one-day 2023 market. The hours are the same, and the shopping now happens along the route, with the square hosting the 5 p.m. ceremony at the end.
For families, Dec. 12 can start a few blocks west. Horner Park, 2741 W. Montrose Ave., is hosting Santa's Secret Workshop that morning from 9:30 a.m. to 12:30 p.m. It's a youth craft event and costs $15. The workshop ends half an hour after the trolley starts, so you can do the crafts in the morning, ride the trolley in the afternoon and walk to the square for the 5 p.m. lighting.
Four dates over three weeks
The one-weekend market has given way to a season spread across November and December. Here are the dates in order, with one nearby event first:
- Nov. 14 and 15, Lycée Français French Market. This one is just outside the neighborhood, at 1929 W. Wilson Ave., but it's on the Northcenter Chamber's calendar. It has artisans, food and activities, with a suggested $5 donation.
- Sat., Nov. 28, Small Business Saturday in Northcenter. 10 a.m. to 8 p.m., based at Town Square, 4100 N. Damen. Store details are on the Chamber's event page.
- Thu., Dec. 10, Northcenter Chamber Holiday Party. 6 to 8 p.m. at Hindsight Community Tavern, 2020 W. Irving Park Rd. It's free for Chamber members plus one guest and $20 for nonmembers and additional guests.
- Sat., Dec. 12, Shop Northcenter Trolley and Tree Lighting. Trolley from noon to 6 p.m., tree lighting at 5 p.m. in Town Square, both free. Santa's Secret Workshop runs at Horner Park that morning.
- Thu., Dec. 17, Northcenter at Night. 6 to 9 p.m., with neighborhood shops staying open late. Locations will be posted on the Chamber's listing.
All four North Center dates send people into the shops. Small Business Saturday falls on the Saturday after Thanksgiving, the trolley carries shoppers between stores, and Northcenter at Night keeps stores open on a weeknight eight days before Christmas.
Two new places on the map this year
A season spread around the neighborhood depends on what's open around it, and the list changed this fall.
Hindsight Community Tavern, 2020 W. Irving Park Rd. It's in the former Prost Florist space. Block Club Chicago reported on Oct. 20 that the tavern was set to open the next day. Owner Ryan Reynolds described it as a tavern with no TVs, built around table games, with cocktails, mocktails and CBD drinks. Less than two months after opening, it's hosting the Chamber's holiday party on Dec. 10. On Irving Park, west of the square, it's an easy stop between a Damen Avenue errand and a walk home.
Jake's Place, 4159 N. Western Ave. Robert Maleski, who founded Milly's Pizza in the Pan in 2020, is opening a thin-crust, square-cut pizzeria in the former Armand's Pizzeria space. Armand's closed in summer 2025. Block Club Chicago reported on Oct. 16 that Maleski was aiming for early December. Maleski told Block Club the pizza will be "the exact opposite of what we make at Milly's," with a crust "as thin as a cracker." Plans call for a short menu of five or six pizzas, served 4 to 9 p.m. Wednesday through Sunday. Those hours line up with the end of the Dec. 12 tree lighting and the Dec. 17 late-shopping night, so check its status before you plan dinner around it.
Planning around the Dec. 12 crowd
When the market ran across a full weekend, crowds had two days to spread out. This year the trolley, the tree lighting and Santa all happen on one Saturday afternoon. Horner Park's workshop adds a morning event on the same day. If you're hosting guests that weekend or planning a family photo with Santa, Dec. 12 is the date to plan around. If you'd rather avoid the crowd, Small Business Saturday on Nov. 28 runs 10 hours, and Northcenter at Night on Dec. 17 runs three, so both have more room.
Hindsight and the Lycée Français market fill in the dates around those days. The French market weekend is this Saturday and Sunday, Nov. 14 and 15, at 1929 W. Wilson.
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