If you are looking for things to do in Healdsburg in winter, the five weeks between Thanksgiving and New Year's are a good place to start. Harvest is over, tasting rooms are quieter, and the town puts real effort into the season: a Thanksgiving morning 5K, a tree lighting and night market on the Plaza, and winery holiday events throughout Sonoma County. Our team lives and works here, and below are the 2026 dates we have confirmed, plus the homes we recommend for a cold-weather stay.
Top photo courtesy of Sonoma County Tourism
Sonoma County Thanksgiving Weekend: Healdsburg Turkey Trot and More
Healdsburg Turkey Trot 2026: Thursday, November 26
The Healdsburg 5K Turkey Trot starts at 8:00 a.m. on Thanksgiving morning at 333 Center Street, in front of Healdsburg Running Company, and finishes in the same spot. It is a fun run and walk, so strollers and slower paces are common. Registration is $25 for adults ($20 without a shirt) and $20 for kids under 12 ($15 without a shirt). Proceeds support the Drew Esquivel Memorial Scholarship for Healdsburg High student-athletes, and the race is run with the Rotary Club of Healdsburg Sunrise and the Healdsburg High Interact Club.
If you stay within walking distance of the Plaza, you can walk to the start and be back in time to get the turkey in the oven.
Holiday Celebration and Marketplace at Dry Creek Vineyard: Saturday, November 28
On Small Business Saturday, Dry Creek Vineyard hosts its long-running Holiday Celebration and Marketplace from noon to 4:00 p.m., with limited-release wines, carolers, seasonal bites and local artisan vendors. It is a 21-and-over event, and children and pets are not allowed.
Geyserville Lighted Tractor Parade: Saturday, November 28
That evening, the Geyserville Tractor Parade runs from 6:00 to 8:00 p.m. Tractors start at 6:15 p.m. at the north end of town and make one pass down Geyserville Avenue. Highway 128 and Geyserville Avenue close to traffic from 6:00 to 8:00 p.m. Restaurants stay open, so reserve ahead, and tasting rooms are open by appointment. Geyserville is a short drive north of Healdsburg, so the parade pairs well with an afternoon at Dry Creek Vineyard.
Holiday shopping downtown
Garrett Ace Hardware and The Gift Horse run a holiday pop-up tent from November 1 through January 5, open 7:00 a.m. to 7:00 p.m., which makes an easy stop between Plaza shops and tasting rooms.
Photo courtesy of Sonoma County Tourism
Healdsburg Tree Lighting 2026 and Early December
Merry Healdsburg: Friday, December 4, 5:00 to 9:00 p.m.
Merry Healdsburg is the City of Healdsburg's signature holiday event, held on the Plaza and surrounding streets. The city lists a tree lighting countdown, free photos with Santa, a holiday night market with local vendors, live holiday music, free carriage rides through downtown and children's crafts. The city also notes a possible snow flurry on the Plaza, if conditions allow.
Parking near the Plaza fills early on tree lighting night. If your rental is a short walk away, you can skip the car entirely and head back for dinner when the crowd thins.
ARTNITE Healdsburg: Thursday, December 3
Stay Healdsburg lists ARTNITE, the town's first-Thursday art walk, on December 3, the night before the tree lighting. It is a good reason to arrive a day early.
More Things to Do in Healdsburg in Winter: Winery Holiday Events
Winter is one of the better times to taste in Sonoma County wine country. Appointments are easier to get, and winemakers often have more time to talk. Two confirmed December events:
- DeLoach Vineyards Holiday Open House, Saturday, December 5. Savory bites, DeLoach wines and music at the Santa Rosa winery. Bring a new, unwrapped toy for Toys for Tots. Times have not been posted yet, and the member allocation is listed as sold out, so check the page before you go.
- Exploration of Caviar at J Vineyards & Winery, Sunday, December 6. A seated session on caviar sourcing and pairings with J's sparkling wines, $275 per person ($250 for club members). Bookings are open.
Every stay with us includes complimentary tastings at our partner wineries, worth up to nearly $2,000 depending on the home. Reservations are required, the guest of record attends, and we send winery contact details once your booking is confirmed. For restaurants and other local favorites, see our Sonoma County local recommendations.
Where to Stay: Winter-Ready Homes Throughout Sonoma County
Walk to the Plaza for the tree lighting and Turkey Trot
- Healdsburg Plaza Gem: two blocks from the Plaza, 2 bedrooms, sleeps 6. A new hot tub with heating included and a fire pit for evenings after the night market.
- Heavenly Hideaway: two blocks from the Plaza on a quiet alley, 2 bedrooms, sleeps 4. An indoor gas fireplace, a private backyard, and small dogs are welcome (pet fee applies).
- Fitch St Escape: two blocks from the Plaza, 2 bedrooms, sleeps 4. A gas fireplace inside and a fire table on the back patio.
- Plaza Street Bungalow: a short stroll to the Plaza, 2 bedrooms, sleeps 4, with a fireplace in the living room.
Hot tubs and fireplaces outside town
- Eastside Eden: about 10 minutes from the Plaza, 3 bedrooms, sleeps 6. An indoor fireplace, a hot tub and a fire pit.
- The Ridge at Mill Creek: 10 minutes from downtown Healdsburg, 4 bedrooms, sleeps 10. Gas fireplaces in the main house and the detached cabin, a hot tub, a fire pit and valley views from the deck. A good fit for families gathering for Thanksgiving.
- Calistoga Cottage: 3 bedrooms, sleeps 7, with an indoor fireplace and a hot tub.
- Calistoga Vista: 3 bedrooms, sleeps 8, with a wood-burning stove, a hot tub and vineyard and Mt. St. Helena views.
Browse all hot tub homes, homes perfect for groups, or current specials. Open dates are on our availability calendar, and you can book direct at liennacollective.com.
Frequently Asked Questions
When is the Healdsburg tree lighting in 2026?
Merry Healdsburg is Friday, December 4, 2026, from 5:00 to 9:00 p.m. on the Healdsburg Plaza, according to the City of Healdsburg.
What time does the Healdsburg Turkey Trot start?
The 5K starts at 8:00 a.m. on Thanksgiving Day, Thursday, November 26, 2026, at 333 Center Street. Register online in advance.
Is winter a good time to visit Sonoma County wine country?
Yes, if you like quieter tasting rooms and holiday events. Many wineries run holiday open houses in late November and December, and appointments are easier to book than during harvest.
Where should I stay in Healdsburg for the holidays?
For the tree lighting and Turkey Trot, a home within walking distance of the Plaza saves you from parking. Healdsburg Plaza Gem, Heavenly Hideaway and Fitch St Escape are each two blocks away. Questions? Contact our team.
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