Last December, Richmond's two holiday traditions ran a week apart. On Saturday, December 6, 2025, the Village held its 55th annual Christmas of Yesteryear inside one building on Main Street, from 9 a.m. to 2 p.m. One week later, on December 13 and 14, the shops along the same street opened their doors for the Cocoa Walk Weekend. The Village newsletter listed them as two separate items on its calendar, and that matches how they work. One event is run by the Village and happens under one roof. The other is run by the merchants and spreads out across downtown.
Both are coming back in 2026 with changes. The Village plans to give its event a new name, and the merchant weekend's organizer is marking its 100th year in Richmond. If you live nearby and want to plan December around Main Street, here's how the two weekends differ.
Two hosts, two formats
| Village holiday event | Cocoa Walk Weekend | |
|---|---|---|
| Who runs it | Village of Richmond | Downtown merchants, organized by Anderson's Candy Shop |
| 2025 date | Saturday, Dec. 6 | Saturday–Sunday, Dec. 13–14 |
| 2026 date | Not yet posted | Saturday–Sunday, Dec. 12–13 |
| Where | The District, 10308 Main St. | Shop to shop, starting at Anderson's, 10301 N Main St. |
| Hours | 9 a.m.–2 p.m. in 2025 | 10 a.m.–3 p.m. both days |
| Cost to join | Free activities; cocoa bar donations encouraged | $2 Cocoa Card, cash |
The Village's 2025 program and this year's Cocoa Walk listing both include Santa and cocoa, so the two events are easy to mix up. What really separates them is where the day happens. One keeps families inside a single venue for a morning. The other sends people in and out of storefronts for two afternoons.
The Village's day, and its new name
Christmas of Yesteryear has been held at The District for at least three years running. In 2023 it was the 53rd annual and ran 9 a.m. to 3 p.m. In 2024 it was December 7, 9 a.m. to 2 p.m. The 2025 lineup, published in the Village's Winter 2025 newsletter, was built for kids and fit into a single morning:
- The St. Joseph's Cookie Walk
- A cocoa bar, with donations encouraged for the Richmond Food Pantry
- Free visits and photos with Santa from 10 a.m. to 1 p.m., plus a holiday bag of goodies for each child
- Free face painting and Christmas ornament making
- A craft sponsored by the Nippersink Library
- Holiday balloon creations from 10 a.m. to noon
- Magic Dave from 11 a.m. to noon
- Local Girl Scout troops caroling downtown from 10 a.m. to noon
The name is what changes next. The Village's FY26–27 approved budget lists "Rebrand Christmas of Yesteryear to Merry Main Street" as one of its objectives. The budget states the goal. It doesn't give a date, a venue, or a program. As of late October, the Fall 2026 newsletter calendar only runs through October, and the Village's newsletter page doesn't list a Winter 2026 edition yet. The Winter 2025 issue was posted in October 2025 and laid out the full December lineup, so the Winter 2026 issue is the place to watch for Merry Main Street details.
The new name does say something. "Christmas of Yesteryear" pointed back in time. "Merry Main Street" names the place. A street-centered name fits the work the Village did downtown in 2025. In that year's newsletter, Village President Toni Wardanian pointed residents to new decorative lighting on West Broadway and updated furniture in Stevens Park, and mentioned "a fun surprise planned for holiday decorating." How the renamed event will use that street is still unknown. That will be clear once the Village posts the 2026 program.
The merchants' weekend, and how the card works
The Cocoa Walk follows its own logic. Anderson's Candy Shop organizes it, according to the event listing on AllEvents. The shop's own 2026 events page lists it for December 12 and 13, 10 a.m. to 3 p.m. Here's how it works:
- Start at Anderson's Candy Shop, 10301 N Main St., and buy a Cocoa Card for $2. Bring cash.
- Follow the map printed on the card from stop to stop.
- Get your card validated at each stop on the trail.
- Each stop gives you a free cocoa to drink there or take home, plus a bonus treat, craft, or sale. The listing says to "think 20% OFF deals."
- If you don't finish on Saturday, the same card works on Sunday.
The listing also promises free visits with Santa on both days, carolers walking around downtown, and, new for this year's listing, live reindeer on Saturday sponsored by Richmond Township. In 2025 the reindeer were at the Richmond Township Building, which Anderson's described as "just two miles from downtown." The 2026 listing doesn't say where the reindeer will be, so check before you plan a Saturday route around them. One quirk: the listing's date header shows the event ending at 3:00 a.m. Sunday. The description says 10 a.m. to 3 p.m. each day, and that's the schedule to go by.
The 2026 participant list and trail map haven't been posted yet. The map comes printed on the card, so you'll get it when you buy one at Anderson's.
The card is a small price to pay, but it does a specific job. Every stop is a business, and every validation gets someone through a door they might have walked past. Anderson's put it plainly in a November 2025 post on its website: events like the Cocoa Walk "are also super important to the success of many small businesses across Richmond. Events like these help keep the doors open and the lights on." The 2025 walk was also a fundraiser for the local food pantry. The 2026 listing doesn't name a beneficiary, so it isn't settled yet whether that will repeat.
A centennial year for the shop at the start of the trail
The weekend begins at Anderson's, and 2026 is a big year there. In June, Shaw Local's Northwest Herald reported that the family business was marking 100 years in Richmond. The story also noted that the Andersons opened their first shop in Chicago in 1919 before moving to Richmond. The celebration lined up with the Village's revived Round-Up festival on June 27 and 28.
The shop runs on a seasonal calendar of its own. It hosted Richmond's Family Fall Fest on October 17 and 18. Its contact page lists fall hours of 9 a.m. to 5 p.m. Tuesday through Saturday and 10 a.m. to 4 p.m. Sunday and Monday. The Cocoa Walk's 10 a.m. start fits inside both of those schedules, so you can pick up a card as soon as the walk opens on either day.
Planning a day downtown around either weekend
Both events draw a crowd onto a downtown that has two kinds of parking. The Village's Winter 2025 newsletter mapped about 263 unrestricted spaces and about 81 spaces in new 2-hour zones. A morning at The District fits easily in two hours. A full Cocoa Walk with lunch and a Santa line may not, so an unrestricted space is the safer choice for that weekend. The newsletter map splits the spaces north and south of the Route 12 bridge. Check it before you arrive.
If you want lunch or more shopping between stamps, these Main Street area businesses appear in the Village's current directories:
- Richmond Café, 10321 N Main St.
- Magpie Market, 10320 N Main St.
- Harper G! Mercantile, 5601 Broadway Rd.
- Oldies & Goodies, 9908 Main St.
- The District, 10308 N Main St., home of the Village event in each of the last three years
These listings tell you who is downtown, not who will be on the 2026 cocoa trail. Your card's map will show that.
Here's how the two weekends played out in 2025. A family with small children could do the cookie walk, Santa photos, and an ornament craft at The District in one morning. Seven days later, the same family could come back with a $2 card and spend an afternoon going in and out of the shops. The Cocoa Walk is already on the calendar for December 12 and 13. Whether Merry Main Street keeps the early-December slot will be clear once the Village posts its winter schedule.
When I'm talking with Richmond homeowners, the conversation often turns to these traditions, the ones that bring people downtown every year. If you have questions about your home or the area this season, Bradley Fox is happy to talk it through over a cocoa on Main Street. Let's Connect.
