Red Wing's 25th Holiday Stroll Opens a Downtown Winter That Runs Until February
November 5, 2026
November 5, 2026
The Red Wing Holiday Stroll runs for 12 hours, from Breakfast with Santa at 9 a.m. to the last parade float. The decorations planned for its 25th edition are meant to stay up for about 11 weeks.
This year the Stroll is on Friday, Nov. 27, the day after Thanksgiving. Its theme, posted on the Holiday Stroll site, is "The one where the Holiday Stroll turns 25." Organizers say they're bringing back traditions from the early years. Two of the biggest changes reach well past that Friday night, though. The first pub crawl runs five days, and the new snowflakes on downtown light poles are scheduled to be lit at the Stroll and left up into February. For people who live here, the anniversary Stroll is the start of downtown's winter season.
Since 2008, 88 illuminated snowflakes have hung on downtown Red Wing's light poles. The Republican Eagle reported in March that after nearly two decades of snow, wind and rain, Red Wing Downtown Main Street wanted to replace them.
The work is split. The city installs, stores and maintains the snowflakes, and Downtown Main Street raises the money to buy them. New ones cost $32,000. The Downtown Philanthropic Collaborative matched community donations dollar for dollar, so the local share came to $16,000. The campaign page puts the purchase at 80 new snowflakes at $400 apiece. The collaborative is made up of four local foundations: the Albrecht-Poss Family Foundation, the Jones Family Foundation, the Red Wing Area Fund and the Wings Foundation.
The Great Snowflake Refresh page on GiveMN shows $16,099 raised from 111 people against the $16,000 goal, and an update there says the goal was met. City of Red Wing Planning Manager Steve Kohn called the arrangement a "unified effort to beautify downtown," according to the Republican Eagle.
The plan announced in March has the new snowflakes debuting at the 25th Stroll and lighting up on Nov. 27. As in past years, they're meant to stay up until mid-February. That timeline was part of the design from the beginning. Shannan Harris, a former Downtown Main Street board member who helped coordinate the first set in 2008, told the Republican Eagle that the board liked that the decorations
"didn't just say 'holiday' or 'Christmas.'"
According to the paper, the idea was to keep downtown festive all winter long. So the decorations lit at a Christmas parade are still up around Valentine's Day.
The Stroll started in 2001, when a group of Red Wingers decided to hold a small holiday gathering downtown. Today Red Wing Downtown Main Street plans it with volunteers, businesses and sponsors. For the 25th, the organizers chose a Friends-themed holiday and, on the Stroll's home page, promised traditions "that will bring you back to the good 'ol days when the Stroll was first started."
The chili feed is the one the Republican Eagle named outright as a returning tradition. Here are the details from the Stroll's activities page and brochure:
"While supplies last" and a 4 p.m. start mean the chili is meant for the early evening crowd, when the outdoor activities get going. The parade comes later.
The Visit Red Wing listing calls the Pub Crawl new this year. It also runs longer than the Stroll itself, from Wednesday, Nov. 25, through Sunday, Nov. 29. Thanksgiving falls in the middle, and the Stroll comes the day after. A $10 passport bundle includes a passport, a koozie, a scratch-off and a button.
Eight places are on the pub crawl page:
The page lists dates but not each venue's hours, so check with a stop before planning around it. Since the crawl runs five days, a passport can be worked through on the Wednesday before Thanksgiving or on Saturday afternoon, when downtown is quieter than on Stroll night.
The Stroll day starts small, gets busy by late afternoon, and ends with the parade. The table follows the 2026 activities page, which also has the brochure for download.
| Time | What | Where |
|---|---|---|
| 9 a.m.–noon | Breakfast with Santa | Elks Lodge |
| 1:30 p.m. | Movie: Dr. Seuss' How the Grinch Stole Christmas | Sheldon Theatre |
| 3:30–6:30 p.m. | Pictures with Santa | Sheldon Theatre |
| 4 p.m. | Story Time with Royal Ambassadors | Listed on the activities page |
| 4–7 p.m. | Horse-drawn wagon rides | John Rich Park |
| 4–7 p.m. | Wild Pyle Acres Petting Zoo | Bush St. |
| 4–7 p.m. | Kids' cookie decorating | Hanisch Bakery and Coffee Shop |
| 4–7 p.m. | S'mores and hot cider | The Depot |
| 4–7 p.m. | Holiday fun with Red Wing Arts | Clay & Creative Center |
| 4–7 p.m. | Sheldon Brass Band | In front of the Sheldon Theatre |
| 4–7 p.m. | Puppy Kisses & Snuggles | Shear Collective |
| 4–8 p.m. | Santa's mailbox | Wonder & Worn |
| 4–8 p.m. | Hot cocoa station from Merchants Bank | 3rd St. |
| 4–8 p.m. | Christmas tree lot | Jordan Court |
| 4–8 p.m. | Live DJ | Corner of Bush St. and 3rd St. |
| 5 p.m. | Tree lighting ceremony | Courtyard at the Sheldon |
| 5–6 p.m. | Carol sing | Christ Church |
| 5:30–7:30 p.m. | Musical performances and holiday treats | Eagle Brook Church |
| 7:30 p.m. | Lighted parade | Downtown |
The same page lists a few more 4 p.m. activities on Bush St. and 3rd St.: the Polar Express, food trucks, and yard games. Vintage snowmobiles will be on display from 4 to 8 p.m.
The St. James Hotel runs its own schedule starting at 4 p.m. Model trains from the Gandy Dancers, face painting and caricatures are on the mezzanine. The Festival of Wreaths and the gingerbread contest are in the Laurentine Room. Caroling and cocktails move between the Courtyard and Tasting Room and The Port and Scarlet Kitchen & Bar. The Port and Scarlet Kitchen are also pub crawl stops, so a passport stamp fits easily into an evening at the hotel.
For a keepsake, the 2026 collectible ornaments are limited-quantity winners of an artwork contest. The ornament page lists Phileo Style and Mandy's Coffee & Cafe as the places to buy them. Because there are only so many, it makes sense to pick one up during Thanksgiving week rather than waiting until Stroll night.
If the snowflakes go up on schedule, they'll still be lit for the rest of downtown's December calendar.
Downtown Main Street's Late Night Thursdays calendar has Music in the Depot on Thursday, Nov. 5, and again Dec. 3. A Holiday Open House at participating businesses follows on Thursday, Dec. 10, from 4 to 7 p.m. The same page lists Josefina's Bistro as coming soon.
The Sheldon Theatre's 2026–27 season fills the gaps between Thursdays:
Put together, the Sheldon courtyard tree lighting on Nov. 27, the Holiday Open House on Dec. 10 and The New Standards on Dec. 20 make a downtown season built around Bush St., 3rd St. and the Sheldon. The snowflakes paid for by those 111 donors are scheduled to stay up until mid-February, well after the last holiday show.
If you want to talk about Red Wing or anywhere else along the river this winter, Tom Bullington Homes is glad to help over a cup of cocoa at the Stroll or a call afterward. Let's Connect.
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