Evanston’s holiday season has a fairly settled rhythm. It opens with a shopping weekend in late November, moves to a tree lighting in the first days of December, and fills in with neighborhood walks, concerts and charity drives until the new year. Most of the downtown programming is organized by Downtown Evanston, the business district’s promotion group. The dates below are the 2026 schedule as Downtown Evanston has posted it.
Small Business Saturday, Nov. 28
Downtown Evanston’s Small Business Saturday runs from 11 a.m. to 5 p.m. on Nov. 28. Shoppers can pick up a Holiday Shopping Passport; spending $100 or more at participating businesses earns a $20 Evanston gift card. A free trolley runs between downtown and the Main-Dempster Mile, which makes it easy to take in both districts in one afternoon. In 2025 the same trolley ran from 11 a.m. to 3 p.m., so hours can shift from year to year.
Other business districts, including Central Street, run their own promotions through the season.
Holiday Light Celebration, Dec. 5
The main downtown event is the tree lighting at Fountain Square, on Davis Street between Orrington and Sherman avenues. This year it is set for Saturday, Dec. 5, from 4:30 to 7 p.m. The Evanston Children’s Choir performs first, the tree is lit at 5 p.m., and more music follows. From 5:30 to 7 p.m., free photos with Santa and Mrs. Claus are offered in the Crystal Ballroom at The Merion, 1615 Chicago Ave., with hot cocoa and treats.
The event has gone by other names. Newspaper coverage from 2012 and 2013 called it the Holiday Bash. Fountain Square has also hosted a menorah lighting; in 2024 that took place on Dec. 26.
Warm Bevvy Walk, Dec. 10
On Thursday, Dec. 10, from 4 to 7 p.m., downtown businesses take part in a self-guided Warm Bevvy Walk, with warm drinks and shopping or dining specials. This year’s beneficiary is the PTA Equity Project.
Parking and the wider calendar
The city has offered free or reduced parking downtown during past holiday seasons. In 2024, a city bulletin described up to two hours of free parking daily from Nov. 27 through Jan. 1. Terms change each year, so check the city’s parking page for the current offer before relying on it.
Beyond downtown, the season brings holiday concerts, theater productions and food and toy drives. Seasonal roundups from the Daily Northwestern and the Evanstonian track the full calendar as dates are announced, and the North Shore visitors bureau keeps a running list of holiday events across the region.
Sources: Downtown Evanston’s holiday page, Chicago’s North Shore Convention and Visitors Bureau, City of Evanston bulletins.