Wicker Park's Rink Waits for the Cold. This Year, Skating Has a Date.

The first time anyone tried to open an ice rink in Wicker Park, the plan was to open on December 5. That was 2015. WickerICE was a new volunteer project at the time, and the first season was meant to start that day. According to WTTW, an unusually warm December and ice damage from a reported break-in pushed that opening back to January 17, 2016.

Eleven years later, December 5 is back on the calendar. The Wicker Park Bucktown Chamber of Commerce has scheduled its Winter Wonderland & Tree Lighting for Saturday, December 5, from noon to 6 p.m. Under the heading "NEW THIS YEAR," it lists free ice skating. The rink in the park itself has always opened only when the thermometer and the volunteer list allowed. This year, skating also has a date you can put on the calendar, and most of the rest of Wicker Park's winter runs on dates too.

A Rink That Opens When the Weather Lets It

WickerICE describes itself as a community-funded, community-maintained, non-refrigerated outdoor rink at 1425 N. Damen Ave. It measures 60 by 120 feet. It's free whenever the ice is frozen, and skaters bring their own skates. The Wicker Park Advisory Council's WickerICE committee runs it in partnership with the Chicago Park District and the 1st Ward alderman's office.

Without refrigeration, the rink's season is set by nature and by people. When Block Club Chicago covered its return in December 2019, it laid out the requirements:

• Five to seven days below 32 degrees before the ice freezes properly
• Volunteers signed up to maintain it, or it stays closed
• Funding from sponsors and patrons, with no money from the Park District or other city organizations at the time

In a cold winter, that can still add up to a real season. The Advisory Council recorded 52 open days in 2018–19. A warm stretch can still wipe out half a December, and the rink's own site now reads "closed for the 2025-2026 season."

December 5 Puts Skating on the Calendar

Winter Wonderland sets the day first and lets skating follow. The Chamber lists the day as free to all. Free skating appears on the same list as photos with Santa, fireside s'mores, holiday rickshaws, a holiday gnome hunt, visits from the Grinch, music and carolers. Santa, s'mores and letters to Santa are set for Metzger Court at 1260 N. Milwaukee Ave. The tree lighting happens in the park at 1425 N. Damen, and the Chamber describes the day's activities as spread across the neighborhood. SSA #33 presents the tree lighting. The Chamber, SSA #33, the Wicker Park Advisory Board and the Chicago Park District put on the event together.

The Wicker Park Advisory Council's own listing gives the same Saturday, noon to 6 p.m. For anyone who has waited out a slushy January for the park ice to firm up, this is the first time skating in the neighborhood comes with a date set weeks in advance.

A Winter Calendar That Doesn't Need Ice

Most of the season works the same way, with a set date and an indoor room or a free street to walk. Here's what's on the Wicker Park calendar from this week through the end of December:

The early December weekend is the busiest stretch. The First Fridays art walk on December 4 falls on the opening night of WE ARE NOT UGLY PEOPLE at The Den Theatre. Winter Wonderland is the next afternoon, and They Are All Our Sons closes on Sunday. That's four dated events in three days, and none of them depends on a cold snap. If you're registering kids for the Park District's winter session at Wicker, sign-up opens online Tuesday, December 8, at 9 a.m. Kiddie College for ages 3 to under 6 runs January 4 to March 18, 2027. Park Kids for ages 6 to under 13 runs January 4 to March 19.

Division Street's Holiday Windows and Warm-Up Stops

The other dated part of the season is on Division Street, where the window displays are the attraction. Planet Access opened its new store at 1905 W. Division St. on September 10. Search360 created the social enterprise with Toad&Co. The store stocks brands chosen for social good, local small business and sustainability, and its proceeds help adults with intellectual and developmental disabilities travel and find more opportunities in their communities. This is the shop's first holiday season on Division. Its annual Winter Windows unveiling was November 5, and the displays stay up through the holiday season at both the Wicker Park store and the original Lincoln Square location. Inside, the new Visibility Arts line includes prints, glassware, greeting cards, playing cards and crewnecks, all designs that weren't sold at Planet Access before this fall.

A short walk east, Buona's The Beef Stand is a walk-up Italian beef window at 1750 W. Division St., next to Original Rainbow Cone. Eater Chicago reported it opened on September 2. On Damen, closer to the park, two newer names have joined the block. Block Club Chicago reported that Hattie B's Hot Chicken set an October 28 opening at 1542 N. Damen Ave., in the former Urbanbelly storefront. The Infatuation added Atelier Shang, a Chinese restaurant at 1613 N. Damen Ave., to its Chicago listings on October 26. Either one is a few blocks from the tree at 1425 N. Damen, close enough to walk to after the lighting on December 5.

Where the Rink's Next Season Gets Decided

WickerICE only opens if the neighborhood supports it. Its site asks for family and individual sponsors at $25, $50 or $100 and up. Sponsors' names are posted at the rink the following season. Businesses sponsor by contacting the committee directly. The volunteer crew handles in-season monitoring and maintenance and also raises money at other Wicker Park events during the off-season. In seasons when the rink is open, it runs free Saturday-morning skating lessons for kids ages 5 to 12 from 10 to 11 a.m. Parents sign up for an hour of volunteer time or make a donation. Stick-and-puck players wear helmets and help resurface the ice when they're done.

The Wicker Park Advisory Council's public community meetings at the Field House are the place to ask about any of this. The next one is tonight, November 12, from 6:30 to 7:30 p.m., and the one after that is December 10. Dogs come to the park all winter, whatever the rink does. The Wicker Dog Friendly Area at Wicker Park and Evergreen covers 0.14 acres and has a dog drinking fountain.

The volunteer rink that needs a week of hard freeze sits at 1425 N. Damen, the same park where the tree lights up on the afternoon of December 5.

At Dwell Wisely Group, we keep an eye on the dates that shape life in Wicker Park, from the tree lighting on Damen to new shops on Division. If you're thinking about what this winter means for your home in the neighborhood, Schedule a Free Consultation and we'll talk it through, ideally over something warm from one of the spots above.