Highland Park's Holiday Season Starts Downtown and Ends in the Ravines

Highland Park's 2026 holiday calendar takes four Saturdays to move from a parking-garage plaza on Central Avenue to a luminary trail in a lakefront ravine. The first stop is free and open to everyone who shows up. The later stops ask for a registration window, a prepaid ticket, or five straight days of very cold weather. Plan for that shift now and the season gets easier from the Saturday after Thanksgiving week through January.

Nov. 21 begins on the most built-up block in town

The season starts at Port Clinton Square, 600 Central Ave., on Saturday, Nov. 21, from 4 to 6 p.m. The City of Highland Park's Holiday Lighting page lists the program and doesn't mention tickets. The City's events index calls the evening free.

The City lists this lineup for the two hours:

• Live music from DJ Julian
• Meet-and-greets with Santa and Hanukkah Harry
• Photos with the menorah and the new America250 tree, plus an archway, a giant sleigh and an inflatable snow globe
• The Frozen Robins Carolers, Time To Dance and the Highland Park High School Choir
• Free popcorn and hot cocoa

The City lists a few things as new for 2026. Olaf joins Anna and Elsa in the square. Santa hands out candy canes, and Hanukkah Harry has gelt courtesy of Dynasty Coins, Jewelry, & Collectibles. A letters-to-the-North-Pole station is courtesy of Bright Bowls.

Because the event is downtown, getting there is easy. There's a parking garage under Port Clinton Square, surface lots nearby, a two-level deck south of Central at First Street and St. Johns Avenue, and a large lot at 525 Central Ave. The Highland Park Metra station on the UP-N line is about a four-minute walk from the square. Pace Route 472 stops at St. Johns and Central, about five minutes away on foot. Cyclists coming from either direction can take the Robert McClory Bike Trail, and bike racks are close by.

The City pairs the lighting with a push for downtown shopping. It notes that readers of Better Magazine voted Downtown Highland Park the best downtown shopping district. On the Saturday before Thanksgiving week, the season's first event sits right next to the storefronts that most need December foot traffic.

Dec. 5 moves west and starts asking for tickets

Two weeks later, the calendar leaves Central Avenue. Saturday, Dec. 5, has three family events at three addresses, and two of them take advance tickets or registration. The times barely overlap, so the day works as a relay if you plan it in order.

The order is the main planning decision. The 11 a.m. breakfast seating overlaps the crawl's 11:30 start, so families who want all three events will want the 8 a.m. seating. The Park District of Highland Park says breakfast tickets include a buffet, beverages, kids' activities, crafts, a visit from Santa and a small gift. Specialty cocktails for kids and adults are sold separately. Groups of up to eight can be seated together, and tickets have to be bought ahead of time.

Winter Wonderland runs on time slots. Families register per child for a window, can arrive any time within it and can stay as long as they like, but everything ends at 5 p.m. Children must come with an adult, and adults don't register. The Park District's list includes a Santa's Toy Shop where kids make a plush toy, a Hanukkah craft, photos with Santa and Mrs. Claus, winter carnival games, dance performances by Park District program participants, custom airbrushed beanies and a Jolly Trolley ride with carolers on board.

Roger Williams Avenue, between the crawl and 2027

The crawl sits in the middle of the day, and it's the one Dec. 5 event that brings families into a shopping district. The City describes it as visits to participating businesses for warm cocoa and holiday cookies, with full details posted on the City's crawl page.

The street is small enough to walk in the hour and a half. The City's Ravinia District directory lists a short run of storefronts:

• Field Violin Workshop at 451 Roger Williams
• Yana's Speakeasy at 465
• Vintage Rescue at 473
• Astra Coffee Roasters at 477
• Abigail's American Bistro at 493
• Happi Sushi at 515 to 517
• Fluffy Bunny at 545
• Steep Ravine Brewing Company at 582
• BWB Shakes at 586
• Piero's Pizza at 647

Braeside Market at 55 St. Johns Ave. and The Chunky Scone at 733 St. Johns Ave. are also in the district.

The crawl also covers the stretch where the district's next food openings are planned. Patch reported in October that the City announced three new concepts for Roger Williams Avenue. Bean Bar and MEZE are planned for 565 Roger Williams in spring or summer 2027, and EATACO is planned for 597 Roger Williams in winter 2027. Both addresses are a short walk from Jens Jensen Park.

By mid-December, the calendar moves into the ravines

On the next two Saturdays, the Park District takes the season outdoors to the trails and the lake, and the format changes again. These events are smaller, all-ages programs where every adult and child registers ahead of time.

Saturday, Dec. 12: Winter Solstice Lantern Walk, 4:30 to 6:30 p.m., $16. The program is listed under Heller Nature Center, 2821 Ridge Road, but its description puts the first hour at Sunset Woods. From 4:30 to 5:30, participants gather natural materials and make nature lanterns. From 5:30 to 6:30, the group walks through the park, stopping for songs, poems and stories from winter traditions around the world, and the evening ends with a warm drink. The Park District invites families to bring a favorite poem or song from their own traditions. Children under 2 are free and don't need to register. Everyone else registers, and children need a paid, registered adult with them. Check the gathering point in your registration confirmation or with Heller at 847.433.6901.

Saturday, Dec. 19: Holiday Nights & Campfire Light, 6 to 7:15 p.m., $16. This program takes the season down to Rosewood Beach, 883 Sheridan Road. The Park District describes making nature ornaments, walking a luminary trail through the ravine and drinking hot cocoa around a campfire if the weather allows. Every child and adult has to preregister.

Dec. 19 through Jan. 4: The Great Ornament Hunt at Heller Nature Center, free. On the same Saturday as the Rosewood evening, Heller starts a self-guided hunt for ornaments hidden in trees along its trails. It runs during trail hours through Jan. 4, 2027. No time slot is needed, so it works well for the quiet days between the holidays or for an afternoon with visiting family.

The progression shows on the map. The season opens in a plaza with a garage underneath and ends at a beach ravine and a nature center's tree line. The amenities change with it, from free cocoa from a stage to cocoa at a campfire if the weather cooperates.

The ice moves the same way

Skating follows a similar pattern. The most predictable option is indoors and the most weather-dependent is outdoors.

Centennial Ice Arena, 3100 Trail Way, has public skating on a season that runs from Aug. 22, 2026, to Jan. 10, 2027. Visit Lake County lists admission at $7, or $11 with skate rental, and a listed window of 11 a.m. to 1 p.m.

The next option opens the day after Thanksgiving, across the town line. Through a partnership with the Glencoe Park District, Highland Park residents can buy Glencoe Weinberg Family Recreation Center skating season passes at the resident rate of $71, or a five-visit guest punch pass for $50. The Weinberg Center at 305 Randolph St. in Glencoe has two lighted, outdoor refrigerated rinks, scheduled to run Nov. 27, 2026, through Feb. 28, 2027, weather permitting.

The free rink at Sunset Woods Park, 1801 Sunset Road, has no opening date. The Park District's outdoor skating page explains why. Staff start flooding only after five consecutive days averaging 20 degrees Fahrenheit or colder and after the ground has frozen five to six inches deep. Spraying and freezing the base and finish layers then takes four more 24-hour days. Once the ice is ready, it's open 9 a.m. to 9 p.m. daily under the park's existing lights. There's no supervision or skate rental, and the ice may close for snow removal or unsafe conditions.

So even after the first stretch of hard cold, Sunset Woods needs at least nine days before anyone skates there. The refrigerated rinks in Glencoe and the indoor arena on Trail Way don't depend on that forecast. Families who want ice for the December school break may want to buy a Weinberg pass in late November and count Sunset Woods as a bonus if it opens.

From Port Clinton Square on Nov. 21 to the last ornament at Heller on Jan. 4, the 2026 calendar covers almost every part of Highland Park. If one of these Saturdays has you thinking about which part of town fits your next chapter, HL2R Group can show you what homes near Central Avenue, the Ravinia District or the lakefront ravines are worth right now. Get your home valuation, and we'll put a current number on your place before the new year.