Riverside's Holiday Stroll Runs on Volunteers. This Winter, the Village Is Asking Who Will Carry the Rest.
November 12, 2026
November 12, 2026
Who actually puts on the Riverside Holiday Stroll? For most of its 50-plus years, the answer was a short one. The Riverside-Brookfield Landmark's 2025 preview of the Stroll quoted committee member Amy Regan saying Brian Brennan "single-handedly organized the Holiday Stroll for three decades." Last year the tree lighting was named the Brian Brennan Memorial Tree Lighting Ceremony in his honor.
That detail matters more this year than it did last December. Over the past two months, the people who run Riverside's calendar have been saying the same thing in public. There are fewer volunteers, the bank accounts are small, and the same local businesses keep getting asked for money. The Stroll on Friday, Dec. 4, is the one evening when nearly that whole network shows up on the same few blocks.
The Village of Riverside's event calendar lists the 2026 Holiday Stroll for Friday, Dec. 4, from 5:30 to 9 p.m. in downtown Riverside. The listing promises twinkling lights, carolers, hot cocoa and holiday music.
The regional Oak Park and Beyond holiday guide adds the anchors for this year:
That last stop starts before the Stroll does. The Riverside Arts Center's Members and Kids Show opens with a reception from 4:30 to 9 p.m. on Dec. 4. It brings together work by RAC members, children who took RAC classes during 2026, ceramics studio members, and staff and board. The show stays up through Jan. 2, 2027, so it's still there after the crowds have gone.
If you want a sense of how the evening usually spreads out, last year's program is a good guide. In 2025, Santa and Mrs. Claus arrived by fire truck at Centennial Park, at Longcommon Road and Forest Avenue, at 5:30 p.m., and the tree was lit at 6. Afterward the evening fanned out along three corridors: Longcommon and East Avenue, Riverside Road and Quincy Street, and both sides of Burlington Street. This year's specific stops may differ.
Read last year's lineup again and look at who was doing the hosting. The Village organizes the big moments, but most of the evening was put on by individual businesses and local groups.
In 2025, the fire pit and s'mores at Riverside Garage, 18 East Ave., were courtesy of Young Life and the Boy Scouts. The Riverside Masonic Lodge at 40 Forest Ave. set up a model train display with popcorn and hot chocolate. Girl Scouts ran a bake sale in front of Village Center. St. Paul VI Parish offered caroling and popcorn at 40 E. Burlington St. Riverside Parks and Recreation ran a holiday treat station at the Water Tower.
The Artisan Market in the train station worked the same way. In its second season last year, one of its vendors was the Riverside Junior Woman's Charity, selling Riverside apparel and throw pillows. Cathy Jean Maloney sold her book "Olmsted's Riverside: Stewardship Meets Innovation in a Landmark Village" at the same market.
Dozens of small hosts make up the Stroll, and for thirty years one person pulled them together.
In October, two of those groups said publicly that they're struggling.
On Oct. 15, Maggie White spoke at the Riverside village board meeting on behalf of Riverside Arts Weekend, the June art fair that has filled downtown since 2008. As the Riverside-Brookfield Landmark reported, she told trustees the group faces "ongoing challenges with fundraising, volunteer engagement and attendance that raise serious questions about our ability to sustain RAW in the years ahead."
RAW President Charlotte Zia told the Landmark that the work for each year's festival begins soon after the last one ends. That means November, December and January are when the fundraising happens and the artist applications get reviewed. "We haven't decided about 2027, but we have a very small bank account," she said. The group has launched a community survey asking residents how much the festival matters to them and whether they'd give time or money.
The other volunteer-run groups show how much a small team can do. Here is how the numbers compare:
| Group or event | What it took | What it produced |
|---|---|---|
| Hop Stop, Sept. 26, 2026, co-organized by Riverside Foods and the Olmsted Society | About 30 volunteers | About 700 attendees and more than $10,000 for the Society's workdays and conservation work |
| Riverside Junior Woman's Charity | $50 annual dues plus required service hours from each member | About $19,000 raised in its previous fundraising effort; $30,000 distributed at the end of the 2024-25 season |
| Riverside Arts Weekend | A small senior planning committee working most of the year | A downtown festival every June since 2008, with its 2027 edition undecided |
Thirty people produced a $10,000 afternoon. A dues-paying charity gave out more in one season than it raised in its previous fundraiser. With that few people involved, a handful of new volunteers would make a real difference, and losing a handful would too.
That October board meeting led to a proposal. As the Landmark reported, Trustee Alex Gallegos responded to RAW's comments by calling for a village-sponsored summit of nonprofit leaders. He's aiming for Jan. 25, 2027, though he said the date isn't final.
The groups he hopes will attend include the Riverside Junior Woman's Charity, the Knights of Columbus, the Lions Club he belongs to, and Riverside Arts Weekend. He also wants "pretty much anyone" who took part in the Sept. 6 community organization event at the Riverside Public Library.
His case for joining forces centered on local businesses:
"Our businesses keep getting hit over and over again for the same sponsorship questions. Our small businesses here in town are asked two or three times a week, at the very least, for donations, and that's asking a lot."
Gallegos also pointed to recent history. The Riverside chapters of the Jaycees and the Kiwanis Club no longer exist. The Riverside Chamber of Commerce was in danger of folding in 2022 before new officers brought it back.
The Chamber's recovery is the hopeful part of this story. On Oct. 15, the same night as the board meeting, the Chamber gave out its first Business of the Year award. The Landmark reported that it went to Riverside Foods, the grocery store at 48 E. Burlington St. Chamber President Arrick Pelton said the criteria were excellence, community and connection. He described the last one as a member who "supports other local businesses and organizations and helps strengthen our Riverside business community." A few weeks earlier, Riverside Foods had co-organized the Hop Stop with the Olmsted Society.
Co-owner Peter Boutsikakis told the Landmark the award "really felt like a vote of confidence," and he credited his staff and co-owner Anthony Garbis.
The Stroll asks very little of you. You show up, have some cocoa, and walk home. The groups behind it need more than that, and the next few months are when they plan. Here is how the calendar lines up:
"When you look back at the 150-plus years [since Riverside's establishment], our community has been made up of volunteers," Gallegos told the Landmark. On Dec. 4, many of those volunteers will be easy to find, handing out cocoa, staffing the Artisan Market tables, and keeping the fire going at Riverside Garage, if last year's lineup holds.
We love Riverside's traditions as much as anyone. If you want to talk about the village, its calendar, or the old homes along the Stroll route, Team Cynthia is happy to chat over cocoa or a phone call. Let's Find Your Perfect Home Together.
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