Highland Park's Holidays Start Saturday at Port Clinton Square, but the Outdoor Ice Waits on the Weather
November 12, 2026
November 12, 2026
Saturday's holiday lighting at Port Clinton Square starts at 4 p.m. sharp. The free skating rink at Sunset Woods Park has no opening date at all. The Park District of Highland Park won't start flooding it until the average temperature has stayed at 20°F or colder for five straight days and the ground has frozen five to six inches deep.
So Highland Park's holidays run on two schedules. Downtown events have fixed dates, times and addresses, and they stack up on the first Saturday of December. The outdoor ice depends on the weather. That's why the indoor sessions at Centennial Ice Arena are the only skating you can plan a week ahead in late November.
The City of Highland Park's Holiday Lighting is Saturday, November 21, from 4 to 6 p.m. at Port Clinton Square, 600 Central Ave. The City's event page lists the program:
There are a few new touches for 2026. Olaf joins Anna and Elsa in the square. Santa will hand out candy canes, and Hanukkah Harry will have gelt courtesy of Dynasty Coins, Jewelry, & Collectibles. Kids can also write letters to the North Pole with materials courtesy of Bright Bowls.
Parking is spread across downtown. There's a garage under Port Clinton Square itself, a two-level deck south of Central at First Street and St. Johns, and a large lot at 525 Central Ave. If you'd rather not drive, the Highland Park Metra station on the UP-N line is about a four-minute walk away. Pace Route 472 stops at St. Johns and Central, about five minutes away. From the north, the Robert McClory Bike Trail connects via Vine Avenue and St. Johns.
Just down the block at 461 Central Ave., Central Brick Society has its first holiday season ahead of it. It's a Lego building studio with a social club, a skill-building lab and curated retail. The Record North Shore reported a grand opening date of Saturday, October 24. The studio's website now says it's open Tuesday through Sunday.
The setup is built for staying a while. According to The Record, visitors can drop in for as long as they like or buy a membership. There's a character workshop for designing a minifigure and a matching trading card, plus a brick bar where you can pick out specific pieces to take home. The studio also hosts adult events where guests may bring their own alcohol. Co-founders Lisa Sanders and Alyssa Pollack chose Highland Park because most of their team grew up here. They named the business after Central Avenue, which co-founder Lisa Sanders described to The Record as "the place where people gather."
The studio also tied its opening to the square. The night before the grand opening, it teamed up with MOO-V-Night to screen "The Lego Movie" in Port Clinton Square.
After the lighting, the calendar goes quiet for a week and a half. Then a craft market and four Saturday events land in about 30 hours, spread across town.
Laid out in order, the Saturday works as one loop. You can do the crawl on Roger Williams around lunch, then head to West Ridge or Second Street in the afternoon. The skate session and the crawl overlap by 40 minutes, so you'll need to pick one for late morning.
After that, the Park District's free Great Ornament Hunt runs from December 19 through January 4. It covers the school break, when the fixed events have mostly wrapped up.
Here's where the weather comes in. Highland Park's three skating options open under three different rules, and the gap between them decides where you can actually skate on any given December afternoon.
| Rink | Location | When it opens | Daily hours |
|---|---|---|---|
| Sunset Woods Park | 1801 Sunset Road, Highland Park | After five straight days averaging 20°F or colder and 5 to 6 inches of ground frost, plus about four days to build and freeze the ice | 9 a.m. to 9 p.m., free, unsupervised |
| Weinberg Family Recreation Center | 305 Randolph St., Glencoe, as listed by the Park District | Season listed as Nov. 27, 2026 to Feb. 28, 2027, weather permitting, on two refrigerated rinks | Check with the Park District |
| Centennial Ice Arena | 3100 Trail Way, Highland Park | Indoors, with public skate sessions on the Park District calendar | Varies by session |
The Sunset Woods rule adds up quickly. Even if a cold snap starts the day after Thanksgiving, five qualifying days plus four days of ice-building puts the first possible skate around Sunday, December 6. That's assuming the ground frost has already set in. A warm stretch resets the count. Once the ice is ready, though, it's the most generous option in town, with free skating twelve hours a day.
The Weinberg rinks are refrigerated, so they don't depend on the weather the way Sunset Woods does. Their listed season starts the day after Thanksgiving.
That leaves Centennial as the only rink with dated sessions for every week between now and mid-December. For the rest of November, the Park District calendar lists these public skate times:
Public skate continues into December, with sessions through December 18. On Thursday, December 17, skating runs from 11 a.m. to 1:30 p.m.
The arena is also growing. The Park District says a 3,400-square-foot Performance Center for off-ice athletic training and conditioning is due in early 2027.
The Cookie & Cocoa Crawl route on Roger Williams Avenue passes two storefronts that will look different by next holiday season. In October, Patch reported that city officials had announced three food concepts for the district, all owned and run by Serah and Kadir Cicek.
At 565 Roger Williams Ave., Bean Bar + MEZE is a $1.75 million project in a dry cleaner space that has sat empty for a long time. It's slated for spring or summer 2027. By day, Bean Bar will be a café serving breakfast and lunch with a focus on gluten-free options. In the evening, the space becomes MEZE, with dinner, cocktails and a covered pergola for year-round patio seating. At 597 Roger Williams Ave., EATACO is planned for winter 2027. The fast-casual taqueria is expanding from Northbrook after seven years on the North Shore.
If those dates hold, Roger Williams Avenue will have a café, a dinner spot with year-round patio seating and a taqueria when next winter's crawl comes around.
If the holidays have you planning a spring sale, now is a good time to start on staging and timing, well before the listing season gets crowded. Deb Baker Homes is glad to walk you through it. Request a complimentary home valuation, and we'll talk through a plan that fits around your December.
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