Sunday, October 25 was the last outdoor day of the 2026 Wicker Park Farmers Market. The Chamber also held Meet Me on Milwaukee that day, closing Milwaukee Avenue from the North and Damen intersection to Ashland. Both are now over until next year.
Three events remain between now and the holidays, and each one works the same way. You get a free route through the neighborhood's businesses and walk it yourself. Trick-or-treat uses a digital map of the business corridors. The November gallery walk is self-guided, with galleries pinned on a map. The December tree lighting is billed as a day to explore the neighborhood and shop local. The Wicker Park Bucktown Chamber of Commerce and Special Service Area #33 run all three, and every one of them routes people along the commercial streets.
| Date | Event | Hours | Cost | Format |
|---|---|---|---|---|
| Saturday, October 31 | WPB Trick-or-Treat | 3 to 6 p.m. | Free | Digital map of business corridors |
| Friday, November 6 | WPB First Fridays | 6 to 8 p.m. | Free | Self-guided gallery map |
| Saturday, December 5 | WPB Winter Wonderland & Tree Lighting | Noon to 6 p.m. | Free | Activities across the neighborhood, ending with the tree lighting |
Saturday's trick-or-treat route runs through storefronts
Halloween is on a Saturday this year. The Chamber's WPB Trick-or-Treat runs from 3 to 6 p.m. along the business corridors of Wicker Park and Bucktown, and participating businesses are shown on a digital map. Businesses sign up to be listed, so the map shows the shops that chose to take part. It isn't a list of every door on Milwaukee or Division.
The route runs past the newest openings, and several of them are near the same intersection.
What changed on Damen this week
Hattie B's Hot Chicken was scheduled to open Wednesday, October 28, in the corner space at 1542 N. Damen Ave., near the Damen Blue Line station, Block Club Chicago reported. Urbanbelly, the Asian street food restaurant, had been in that space since 2016 and moved to Fulton Market earlier this year. This is the Nashville chain's second Chicago location. The first opened in Wrigleyville in February.
The menu has jumbo tenders, sandwiches, and half-bird platters at heat levels from no spice to Nashville hot. Sides include pimento mac and cheese, collard greens, and bacon-cheddar grits, and desserts include banana pudding and peach cobbler. There's indoor and patio seating.
The brand has been in the neighborhood before. In Block Club's report, executive chef Brian Morris said in a press release:
"Chicagoans have always shown us a lot of love, and Wicker Park is a special spot for us. It was the first place in the city we brought Hattie B's to, back when we did a pop-up at Dove's Luncheonette in 2019."
For the opening, Hattie B's made a limited-run pizza with Paulie Gee's Wicker Park, just north near Milwaukee Avenue. It comes with hot chicken tender bites, Hattie B's barbecue sauce, bacon, greens, and a corn and black-eyed pea succotash, at $5 a slice or $37 for a full pie. It's a limited run, so if the Paulie Gee's stop is on your Halloween route, go early in the season.
A few steps away, Blank Street Coffee is getting ready to open at 1588 N. Milwaukee Ave., the former Starbucks at the North, Damen and Milwaukee intersection, according to Block Club. Time Out Chicago also reported in early October that no opening date had been set. For now, the corner coffee spot is still empty.
To the southwest on Division, Buona's The Beef Stand has been open since Wednesday, September 2. It's a walk-up Italian beef window at 1750 W. Division St., Eater Chicago reported. A walk-up window fits a season of outdoor walks, since you order without sitting down.
Put together, the season's three openings sit on Damen near the Blue Line, at the six-corner intersection, and on Division. Those are the corridors the Chamber's maps are built around.
November 6: the gallery walk
The second map is for art. The Chamber's WPB First Fridays gallery walk is Friday, November 6, from 6 to 8 p.m. It's free and self-guided, and galleries, pop-up galleries, and other art spaces open their doors so visitors can talk with owners and artists. The November map includes the Flat Iron Arts Building and Jackson Junge Gallery.
The walk lasts two hours on an early-November Friday, so it will probably be dark from the start. A practical plan:
- Pull up the November map before you leave home. The stops are pinned there.
- Start at the Flat Iron Arts Building, which holds several studios under one roof.
- Pick the rest of the stops by distance. Two hours covers a handful of galleries, not all of them.
- End near the Damen corner if you're staying out for dinner afterward.
December 5: the tree lighting adds skating
The third map ends the season. The WPB Winter Wonderland & Tree Lighting is Saturday, December 5, from noon to 6 p.m., and everything listed is free. The Chamber lists these activities:
- Free photos with Santa
- Fireside s'mores
- Holiday rickshaws
- A holiday gnome hunt
- Visits from the Grinch
- Holiday music and carolers
- The Wicker Park Holiday Tree Lighting, presented by WPB SSA #33
This year the Chamber is also adding free ice skating, which it labels "new this year" and places "right in the heart of Wicker Park Bucktown." Skating wasn't on the 2025 program, which listed Santa photos, s'mores, rickshaws and the gnome hunt. The Chamber hasn't said exactly where the rink will be. Check the event page closer to the date before you bring skates.
Last year's Wicker Park Advisory Council schedule put fountain decorating, children's activities, and a 5 p.m. tree lighting in Wicker Park. The Chicago Park District lists the park at 1425 N. Damen Avenue. The 2026 event is presented by the Chamber, SSA #33, the Wicker Park Advisory Board, and the Chicago Park District. The 2026 hours start at noon, while the 2025 Chamber listing started at 1 p.m., so there's an extra hour this year.
The Chamber's tagline for the day is "Shop Small. Support Local. Celebrate Together." Like trick-or-treat and the gallery walk, the free activities are spread around the neighborhood so people walk between them and pass the shops on the way.
Where the three routes cross
The routes overlap. Trick-or-treat covers the business corridors. The gallery walk covers Milwaukee's art spaces. Last year's tree lighting was in the park on Damen. All three pass the stretch where Hattie B's took over Urbanbelly's corner, Blank Street is preparing the former Starbucks, and Paulie Gee's is selling the hot-chicken pizza. The newest businesses in the neighborhood are on the same few blocks the season's free events lead you to.
Carol Collins follows these corners the same way she follows the market. She knows which storefronts are changing hands, which openings are bringing people to a block, and how an intersection like Damen, North and Milwaukee changes from one season to the next. If you're thinking about what that corner means for your own Wicker Park address, Carol Collins would be glad to walk through it with you. Book an appointment.
