Winter might just be the most underrated time to experience Wine Country. The crowds have thinned, the air carries a peaceful hush post-harvest, and holiday fun brings a festive feeling throughout the region. This time of year, Sonoma comes alive with joyful celebrations, cozy wine tastings, and an abundance of seasonal charm.

Whether you’re planning a winter getaway or enjoying the holidays close to home, these annual Sonoma County events offer the perfect blend of wine, food, and merriment.

For a full list of what’s coming up this season, visit our Holiday Event page.

Lighting of the Sonoma Plaza

November 22, 2025
Cost: Free

The Sonoma Plaza in the town of Sonoma is a national historic monument, an eight-acre park with stately trees and quiet, pedestrian pathways. From November 22 until the end of the year, these trees will be filled with more than a quarter-million lights (not to mention winter wonderland cheer) to usher in the holiday season. Come out for the Lighting of the Sonoma Plaza on November 22 in particular, as there will be a tree lighting ceremony, musical and dance performers, plus plenty of local food, wine, hot cider, hot chocolate, and sweet treats.

Visit: Sonoma Plaza – 453 1st Street East, Sonoma, CA 95476
Contact: (707) 938-3681

Santa Rosa Turkey Trot

November 27, 2025, 8:30 AM
Cost: $46.58, $17.43 for children under 5

Before some typical Thanksgiving gluttony, work up an appetite with friends and family at the Santa Rosa Turkey Trot. You can walk or run the 5k, depending on how speedy you want to be—the most important thing is that you gather your loved ones and get moving. Prizes will be awarded to the top three male and female finishers, and also given for great turkey costumes, so trot festive! In addition to getting your blood flowing (and working off some of those pumpkin pie calories), know that your entry is going to a good cause. Event benefits will go to local charities, so you’ll be spreading that holiday cheer while getting in a bit of exercise.

Visit: Old Courthouse Square – 50 Old Courthouse Square, Santa Rosa, CA 95404

Cirque de Bohème

Select dates November 28 through December 28, 2025, 2:00 and 4:00 PM
Cost: $45 for adults, $38 for kids 15 and younger

No need to go to Paris, or even Las Vegas, to see the spectacle that is a Cirque show. At Cirque de Bohème in Sonoma, you’ll find gravity-defying acrobatics, impressive balancing acts, and entertaining mimes in this performance inspired by the French circus tradition of the 1920s—think Moulin Rouge, but with a holiday twist. This fantastical event is sure to transport you to a magical world filled with enchantment, adventure, and wonder.

Visit: Cornerstone Sonoma – 23570 Arnold Drive, Sonoma, CA 95476 
Contact: (707) 933-3010

Winter Lights

November 28 – December 31, 2025
Cost: Free, ticket pricing varies for ice skating

Head to Santa Rosa this holiday season when Winter Lights descends upon downtown’s Courthouse Square. Kicking off with a Tree Lighting Ceremony on November 28 from 4 – 7 PM, complete with live entertainment, holiday drinks and treats, and photo ops with Santa, the fun continues with Skating on the Square, featuring kids’ skate clinics with Snoopy, and even a New Year’s Eve Skating Show to close out the holiday season. Adding to the festivities is the Handmade Holiday Crafts Fair from December 6 – 7, as well as restaurants offering holiday specials, and more.

Visit: 90 Old Courthouse Square, Santa Rosa, CA 95404
Contact: (707) 543-3200

Merry Healdsburg Tree Lighting

Healdsburg Plaza
Dec 5, 2025, 5:00 PM – 9:00 PM

The charming town of Healdsburg is bringing the merry vibes this season when its downtown plaza transforms into a winter wonderland fit for the whole family. The Merry Healdsburg Tree Lighting kicks off with, you guessed it, a tree lighting ceremony at 6:00 PM, followed by plenty of ways to get into the holiday spirit—think family activities, carolers, live music, hot chocolate, carriage rides, and a visit from Santa, naturally.

Visit: Healdsburg Avenue and Matheson Street, Healdsburg, CA 95448
Contact: (707) 431-2852

Christmas at Jordan

December 6, 2025, 1:00 – 4:00 PM
Cost: $175

Jordan Winery turns up the holiday magic with sparkling décor, live music, and an afternoon of exceptional wine and food pairings during their Christmas at Jordan event. Guests can sample oysters, caviar, and artisan cheese alongside pours of Jordan’s Chardonnay and Cabernet Sauvignon, then explore rare magnums and festive surprises. Bring an unwrapped toy or gift card for Toys for Tots and celebrate the season in true Wine Country style.

Visit: Jordan Winery – 1474 Alexander Valley Road, Healdsburg, CA 95448
Contact: (707) 431-5250

Winter Wineland

January 17 – 18, 2026, 11:00 AM – 4:00 PM
Cost: $95

Sometimes, with all the feastly holiday events in months past, life feels a little flat on the other side of the new year. Kick the celebration back into gear with the annual Winter WINEland in Northern Sonoma County. All participating wineries will highlight a vintage, varietal, or vertical tasting for the weekend, so it’ll be a great time to meet winemakers, taste limited production wines, new releases or library wines, and restock your wine cellar.

Visit: Various Wineries in Northern Sonoma County