Highland Park's First December Weekend Runs Through the Ravinia District
November 5, 2026
November 5, 2026
On Saturday, December 5, Highland Park's busiest holiday stretch starts on Roger Williams Avenue. The Ravinia District Cookie & Cocoa Crawl begins at 11:30 a.m. at Jens Jensen Park. The Park District's Winter Wonderland covers the afternoon, and that night Ravinia's Dallas Brass concert is the fourth of five consecutive days of shows in Bennett Gordon Hall.
The crawl also passes a block that is changing. In the past four months, the City Council has approved or weighed grants for a diner, a café and lounge, and a taco spot along the same stretch of Roger Williams. The holiday crowd will walk past storefronts that are being rebuilt with public money.
Downtown Highland Park goes first. The City's 2026 Holiday Lighting is Saturday, November 21, from 4 to 6 p.m. in Port Clinton Square at 600 Central Ave. New this year are an America250 tree, Olaf joining Anna and Elsa, gelt from Dynasty Coins, Jewelry & Collectibles, and letter-writing to the North Pole hosted by Bright Bowls. One calendar listing gives a different time slot, so check the event page before you head out.
Parking options include the garage under Port Clinton Square, the two-level deck south of Central on First Street and St. Johns, and the lot at 525 Central Ave. The Highland Park Metra station on the UP-N line is a four-minute walk away.
That covers downtown's big night. Two weeks later, the season moves to the Ravinia District.
Three separate organizers have booked the same Saturday, and the times fit together with almost no gaps.
| Time | Event | Where | Cost |
|---|---|---|---|
| 11:30 a.m. to 1 p.m. | Ravinia District Cookie & Cocoa Crawl | Along Roger Williams Ave., hub at Jens Jensen Park, 540 Roger Williams | Free |
| 2 to 5 p.m. | Winter Wonderland | West Ridge Community Center, 636 Ridge Rd. | $15 resident, $17 non-resident, per child |
| 6 p.m. gates, 7:30 p.m. show | A Merry Christmas with Brass, featuring the Dallas Brass | Bennett Gordon Hall at Ravinia | $35 to $45 |
The crawl is presented by the City of Highland Park and the property owners of Ravinia District Special Service Area 17. Participating businesses serve cocoa and cookies. As of late October, the crawl page still said more details were coming.
Winter Wonderland includes elf training, a plush toy and a Hanukkah craft for each child, plus a one-on-one visit with Santa in his workshop with a family photo to take home. Registration is per child, and each child needs an adult with them. Families can arrive any time during their registration window, and the event ends at 5 p.m.
The concert at the end of that Saturday is one of five. Ravinia's Winter Weekend Series runs December 2 through 6 in Bennett Gordon Hall:
Gates open at 6 p.m. for the evening shows. Ravinia says its prices include fees and may change.
The series name has been used before. In December 2025, Ravinia billed a Take 6 concert on December 3, moved from October 24, as part of the Winter Weekend Series. This year the name covers five shows in a row, Wednesday through Sunday, with both Chanukah and Christmas programs. For anyone who lives near the park, that means four evenings and a Sunday matinee of concertgoers in early December, when the Pavilion lawn is usually empty.
The crawl stays on Roger Williams, so it passes the businesses that are already open. The City's Ravinia District directory lists these, among others:
None of these has been announced as a crawl stop yet. The list shows what is within walking distance of Jens Jensen Park between cocoa and Winter Wonderland. It also leaves out what's missing: there is no diner on the strip, and 565 Roger Williams has been empty for years.
Vintage Rescue moved one door down for a reason. The Record North Shore reported in August that owners Richard and Faye Rosenberg plan to open Faye's Diner at 473 Roger Williams Ave. in February 2027, after the City Council approved two grants on August 17. The diner will serve breakfast, lunch, dinner and desserts. Darcy Mosconi, owner of Sandy's Diner on Sheridan Road in Highwood, will run Faye's as well. The grants are a $150,000 food and beverage interior improvement grant and an exterior improvement grant of up to $12,773. Richard Rosenberg told The Record that Faye's Diner could not open without them, and he described the City as "helpful" and "generous." A City staff report quoted in the same story says the diner offers something "distinct" from the district's current business mix.
The bigger project is a few doors east. According to The Record's July report, Bean Bar is working toward opening at 565 Roger Williams by summer 2027. The City says the building has been vacant for at least a decade. Bean Bar was founded in Northbrook in 2025. It runs as a café and lounge with breakfast, lunch, coffee and baked goods, daytime co-working, and dinner and cocktails in the evening. Highland Park would be its second location.
The grant terms show how much the City wants this building filled. The exterior improvement program is a matching grant of $20,000 a year. City Manager Ghida Neukirch recommended combining five years of that money so Bean Bar could receive $100,000, since the owners are investing about $1.5 million in the property. In exchange, Bean Bar could not apply for the grant again for five years. The plans include a new patio with lounge seating and communal and café tables. Bean Bar's owners, Kadir and Serah Cicek, also own Eataco, which is planning a Ravinia location at 597 Roger Williams and asked for a $20,000 exterior grant.
This is the second try at 565. The Record reported that the Community Restaurant Group pitched a concept for the building in late 2024 and was awarded grant funds, but the project fell through before work began and the money was never paid out.
That gives the December 5 crawl a clear before-and-after. This year, people with cocoa in hand will walk past 473 under construction and 565 still empty. If Faye's opens in February and Bean Bar opens next summer as planned, the 2027 crawl could include a diner and a café patio on the same stretch of Roger Williams.
If you want to talk about what these changes on Roger Williams could mean for homes near the Ravinia station, or you're thinking about where your own household fits in Highland Park, Rhonda Hoff would be glad to start that conversation over cocoa this December. Let's Connect.
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