At 4 p.m. on three Thursdays in December, luminaries will line Main Street in downtown Stillwater. Shops along the street plan their own specials and events for those evenings. Each of those Thursdays is also the first night of one of Community Thread's Hometown for the Holidays weekends, two days before that weekend's Saturday crowd shows up.
Alongside its four weekends, the 2026 schedule includes three Luminary Thursdays, themed holiday karaoke on Tuesdays, and a Thursday-morning 5K on Thanksgiving. You can do much of the season on weeknights and skip the busiest hours.
The Courthouse Weekend Comes Before Any of It
The season's first downtown event happens this coming weekend, before the Hometown for the Holidays program begins. Washington County's Christmas at the Courthouse runs Saturday, November 21, from 10 a.m. to 4 p.m., and Sunday, November 22, from 11 a.m. to 3 p.m., at the Washington County Historic Courthouse, the oldest courthouse in Minnesota.
According to the Discover Stillwater event listing, 30 local vendors will sell handmade art, pottery and leather goods, and the Eggroll Queen food truck will be serving. Kids can do a Christmas scavenger hunt through the building and win candy canes. Santa will be there from 1 to 4 p.m. on Saturday and noon to 2 p.m. on Sunday, with coloring sheets and a mailbox for letters. Admission is free. Donations go to restoring the courthouse.
The listing says the event usually draws 1,500 to 3,000 visitors over the weekend. Sunday is shorter at four hours and has the later start.
Every Event Weekend Opens on a Thursday
Community Thread's program runs four weekends and raises money for its Holiday Hope program. Participating downtown businesses collect new, unwrapped toys on the event days. Each December weekend begins on a Thursday, and the luminaries mark that first night.
| Weekend | Thursday opener | Saturday anchor |
|---|---|---|
| Small Business Weekend, Nov. 27–29 | Nov. 26, 8:30 a.m., Fox Trot 5K with Wild River Running | Small Business Saturday, Elf Takeover noon to 5 p.m., Santa 2 to 4 p.m. |
| Twinkle Weekend, Dec. 3–6 | Dec. 3, 4 p.m., first Luminary Thursday | Chestnut Plaza tree lighting, 4:30 to 6:30 p.m. |
| Candy Town Weekend, Dec. 10–13 | Dec. 10, 4 p.m., second Luminary Thursday | Gingerbread House Contest at Darn Knit Anyway's Makers' Lounge |
| Paws & Claus Weekend, Dec. 17–20 | Dec. 17, 4 p.m., final Luminary Thursday | Pet Parade & Costume Contest, noon |
On a Thursday you get the decorated storefronts and the luminaries without the Saturday program. The Great Gingerbread Man Hunt works the same way. Hidden gingerbread ornaments go up in shops around town on Monday, November 30, and stay up through Sunday, December 20. You pick up a stamp card at any participating business and turn in your finished sheet at River Bank Gift & Decor. With a three-week window, a Thursday evening covers the hunt as well as a Saturday afternoon does.
Tuesday Is the Low-Cost Night Downtown
The Tuesday half of the calendar is at Ziggy's on Main, which hosts holiday karaoke on Tuesdays in December. Each night has a theme:
- December 1: White Out
- December 8: Holiday Characters
- December 15: Holiday PJs
- December 22: Ugly Sweater
Tuesday also matters for parking. In June, the Pioneer Press reported that downtown has paid parking from 10 a.m. to 10 p.m. all year at $1 per hour, and that city-owned lots are free on Tuesdays. On Main Street between Mulberry and Nelson streets, the paper said, parking is a free 90-minute quick zone.
Parking rules have been under discussion this year. The same Pioneer Press story said enforcement picked up in early April and that residents and downtown workers brought complaints to the Downtown Parking Commission. In July, the paper reported that the city was adding 15 free 15-minute quick-stop spaces, mostly on Main Street, plus a 30-minute loading space near Stillwater Mills. The city calendar shows the commission meeting on November 19 and again on December 17, the night of the final Luminary Thursday.
Under the structure the paper described, an evening of karaoke on a Tuesday costs nothing to park in a city lot. The same evening on a Friday is metered until 10 p.m.
The Saturdays That Run on a Clock
The midweek dates work as a calendar because the Saturdays are packed into short windows. Twinkle Weekend's tree lighting on December 5 is the most tightly timed event of the season:
- 4:30 p.m.: The ceremony opens at Chestnut Plaza with Elsa and Olaf, Victorian carolers, and free twinkle lights for kids.
- 5:00 p.m.: Santa arrives on a fire truck.
- 5:30 p.m.: The Chestnut Plaza Christmas tree is lit, followed by fireworks over the river.
Families bringing a new, unwrapped toy for Holiday Hope can also get a photo with Santa.
Candy Town's Saturday, December 12, centers on the Makers' Lounge at Darn Knit Anyway. Visitors can see and vote on the Gingerbread House Contest and decorate cookies there, and Santa is scheduled to make a surprise visit. He also walks downtown from noon to 2 p.m.
Paws & Claus Weekend has the fullest Saturday on the calendar. At noon on December 19, the Pet Parade & Costume Contest starts at LORA Event Center and follows Santa down Main Street. Every participant gets a swag bag for both pet and owner, and the grand prize is a night at Lora Hotel. Victorian carolers sing around downtown from 3 to 5 p.m. At 7 p.m., St. Croix Valley Opera presents Home for the Holidays at Trinity Lutheran Church with Aria Nouveau, the classical crossover duo of soprano Laura Auer and tenor Jay Dref. On Sunday, December 20, the last day of the program, LORA Event Center hosts puppy yoga with French Bulldogs.
The first weekend's Saturday is spread over the whole afternoon. On November 28, elves are out from noon to 5 p.m. with games, gift card giveaways and free Shop Small gift bags. Santa walks downtown from 2 to 4 p.m., and Victorian carolers sing from 3 to 5 p.m. On Sunday, November 29, carolers are back on Main Street from 1 to 3 p.m., and Santa returns from 2 to 4 p.m.
After December 20, the Season Moves to a Parking Lot
The Hometown for the Holidays program ends Sunday, December 20. The next morning, the city calendar lists an outdoor ice rink opening in Parking Lot 4 at 101 Water Street South, just outside Water Street Inn. The city's listing runs from December 21, 2026, through March 22, 2027. When no organized event has the ice, public skating is free. Questions about the rink go to Water Street Inn.
That puts free downtown skating on the calendar for about three months after the last luminary goes out, a longer run than the whole holiday program.
Main Street also has a new name to watch at 324 S. Main St., the former Tilted Tiki space. In July, the Pioneer Press reported that Dave Dahl's Tornado Room Bar & Grill was planned there as a sports and live-music bar with a patio on Main Street. The partners are Dave Dahl, Ziggy's founder Paul Barber, and restaurant veteran Dave Eichten. Barber told the paper that a tornado siren would set off five minutes of half-price drinks. Updates on the opening are posted at tornadoroomstillwater.com.
If the holidays have you thinking about where in Stillwater you want to spend more of your weeknights, or about the house that makes that walk to Main Street possible, Smitten Real Estate Group would be glad to talk it through over coffee downtown. Let's Connect.
