At 8 a.m. on Thanksgiving, runners will line up at 333 Center Street for the Healdsburg Turkey Trot. Twenty-three days later, on Saturday, December 19, the Healdsburg Certified Farmers' Market closes its season at 3 North Street. That evening the Marcus Shelby Orchestra plays Duke Ellington and Billy Strayhorn's Harlem Nutcracker Suite at the Raven Performing Arts Theater.
Everything else on downtown's holiday calendar this year falls between those two dates, with the busiest stretch in the first weekend of December.
Thanksgiving morning starts the count
The Healdsburg 5K Turkey Trot runs on Thursday, November 26. The start is at 8 a.m. from 333 Center Street. Adult registration costs $25 with a shirt and $20 without. Children under 12 pay $20 with a shirt and $15 without. Race-day registration opens 90 minutes before the start, so it begins at 6:30 a.m. for anyone who decides that morning.
The Rotary Club of Healdsburg Sunrise and Healdsburg Running Company present the race in partnership with the City. All proceeds go to Live Like Drew, the Drew Esquivel Scholarship Fund for Healdsburg High School scholar-athletes, and to other local nonprofits. The City's 2026 Master Calendar of Events lists the course on downtown streets.
Two days later, on Saturday, November 28, the farmers' market opens at 8:30 a.m. as usual. From that weekend through the season's last day there are four Saturday markets left: November 28 and December 5, 12 and 19.
The pavilion's first December
The market's location is new this year, and that changes the season's geography. The Foley Family Community Pavilion at 3 North Street held its official opening weekend on March 21 and 22, 2026, and that Saturday included a pop-up farmers' market. The regular Saturday market followed on April 11. According to the Healdsburg Farmers' Market, it runs 8:30 a.m. to noon at the pavilion, a short walk from the Plaza, through December 19. The City's master calendar counts 37 Saturday market days for the year.
This is the first holiday season with the market at the pavilion. The market's visit page lists a Fall/Holiday Craft Market running from October through December 2026 and says more demos and events are still being planned. Check that page for specific craft-market Saturdays. The one firm date is the close of the regular Saturday season on December 19.
The pavilion also hosted much of downtown's summer and fall calendar, including the Tuesday market, the Healdsburg Jazz gala and Howl-O-Ween. By December the Saturday morning market is its last recurring event of the year, and the holiday evenings move back to the Plaza.
December 4 through 6 is the crowded weekend
The first weekend of December holds more events than any other in the season.
Merry Healdsburg runs Friday, December 4, from 5 to 9 p.m. on the Plaza. Admission is free. The City's program gives a timeline:
- 5:00 to 5:30 p.m.: the Healdsburg Chorus performs
- 5:00 to 8:00 p.m.: horse-drawn carriage rides
- 5:00 to 9:00 p.m.: the Holiday Night Market, plus holiday crafts all evening
- By 6:00 p.m.: arrive for the tree-lighting ceremony
- After the lighting: photos with Santa
- 6:45 to 8:45 p.m.: a special musical performance
City of Healdsburg Community Services hosts the evening in partnership with the Healdsburg Chamber of Commerce. As of late October, the City had not named the 6:45 performer.
Three more events fall on the same night or the two days after it:
| Event | Date and time | Location | Admission |
|---|---|---|---|
| Mostly Kosher | Fri., Dec. 4, 7:30 p.m., doors 6:30 | Raven Performing Arts Theater | $29 general, $49 gold, $69 front of house |
| Holiday Artisan Market, first year | Sat. and Sun., Dec. 5 and 6, 11 a.m. to 5 p.m. | Appellation Healdsburg, 101 Dovetail Lane, indoors | Not listed |
| Healdsburg Museum Holiday Homes Tour | Sun., Dec. 6, 11 a.m. to 3 p.m. | Homes within walking distance of the Museum | $75, or $50 for Museum members |
Mostly Kosher's doors open at 6:30, while the night market is still running and the tree has just been lit. The Raven's events listing describes the band as "a global food-fight of Jazz, Latin, Rock, and Folk." The ticket prices in the table are listed with fees included. The same Friday, the Chamber lists Holiday After Hours at Rodney Strong from 5:30 to 7:30 p.m., at $30 general admission or $24 for club members. That puts at least three ticketed or scheduled options in the same evening window.
On Saturday, December 5, the farmers' market opens at 8:30 a.m. at the pavilion. Appellation's Holiday Artisan Market opens at 11, with local and visiting makers, which allows a morning at North Street followed by an afternoon at Dovetail Lane. On Sunday, the Healdsburg Museum's Holiday Homes Tour runs from 11 to 3, with every home on the tour within walking distance of the Museum.
For dinner near the Plaza that weekend, Baci Café and Wine Bar at 336 Healdsburg Avenue sits one block away. According to the Healdsburg Tribune, the café and wine bar has been taking reservations again since July 30.
The middle weekends are for choirs and Marcus Shelby
After December 6 the calendar slows down, and the same performers start to return. The Healdsburg Chorus, which opens Merry Healdsburg at 5 p.m., gives its own concerts, Winter Illuminations, at the Raven on Saturday and Sunday, December 12 and 13. Both shows start at 3 p.m. with doors at 2. General admission is $25 with no fees. The Raven's listing gives a program that runs "from Vivaldi and Lauridsen to Irving Berlin, John Williams, and beloved traditional carols," with communal singing.
Marcus Shelby appears twice in December. On Saturday, December 12, Healdsburg Jazz presents its Family Matinee Concert Series with the Marcus Shelby Quartet featuring Stella Heath at Healdsburg Community Church, from 11 a.m. to noon. That is two and a half hours after the farmers' market opens, and four hours before the Chorus's first Winter Illuminations show. A week later, on December 19, he leads his full orchestra at the Raven.
On Friday, December 18, the night before the finale, the Raven hosts the Christmas Jug Band and Shana Morrison. The poster bills it as "The Christmas Jug Band's 50th Sleighride." The show starts at 7:30 p.m. with doors at 6:30. Tickets are $29 general, $44 gold and $64 front of house, fees included. The band's lineup includes Greg Dewey, Tim Eschliman, Paul Rogers and Snakebite Jacobs.
December 19, morning and night
Saturday, December 19, holds both ends of the season:
- 8:30 a.m. to noon: the last Saturday market of the regular 2026 season at the Foley Family Community Pavilion, 3 North Street. The market's own pages do not yet list a schedule beyond that date.
- 6:00 p.m.: doors open at the Raven for Healdsburg Jazz's Harlem Nutcracker Suite.
- 7:00 p.m.: the Marcus Shelby Orchestra performs Ellington and Strayhorn's arrangement of the Nutcracker. Admission is $29 to $104, fees included.
The City's 2026 master calendar lists one more event after Merry Healdsburg, the Senior Appreciation Dinner at Villa Chanticleer on Sunday, December 6. No other permitted downtown event appears on it after the first week of December. From mid-December on, the season's last dates come from the Raven, Healdsburg Jazz and the market's final Saturday, and all three land on December 19.
If you are thinking about a place within walking distance of the Plaza and the pavilion on North Street, Graham Sarasy can walk you through the downtown blocks and what each one offers through the year. Request a confidential consultation.
