Celebrate November and December in Sonoma Wine Country
Holidays in Healdsburg: Events, Dining & Winter Getaways
The holidays are a wonderful time to visit Healdsburg, California. From festive celebrations and seasonal wine tastings to holiday shopping around Healdsburg Plaza, November and December bring plenty of reasons to plan a Sonoma Wine Country getaway.
Explore local holiday events, discover restaurants serving Sonoma County flavors, and browse charming boutiques and farmers markets for one-of-a-kind gifts. Make The Lodge at Healdsburg your home base for a relaxing holiday escape.
Explore Holiday Events & Experiences in Healdsburg
Wine Road's Wine & Food Affair
Date: November 7-8, 2026 | 11:00 AM-4:00 PM
Location: Participating wineries throughout Alexander Valley, Dry Creek Valley, and Russian River Valley
Experience a weekend of exceptional Sonoma County wines paired with delicious bites at more than 50 participating wineries. Explore Northern Sonoma County's wine regions at your own pace while discovering new favorites.
Heritage Healdsburg: Past & Present
Date: November 12, 2026 | 6:00-9:00 PM
Location: Villa Chanticleer, 900 Chanticleer Way, Healdsburg, CA
Celebrate Healdsburg's rich history and vibrant community at Heritage Healdsburg: Past & Present. Hosted by the Healdsburg Chamber of Commerce, this special evening features local business awards, food, drinks, and a celebration of the people and traditions that have shaped Healdsburg over the years.
Windsor Winter Wine Walk
Date: November 19, 2026
Location: Windsor Town Green, Windsor, CA
Enjoy an evening of wine tasting, local food, and shopping during this seasonal event in nearby Windsor. Stroll through participating businesses while sampling wines from more than 25 wineries.
Healdsburg Turkey Trot
Date: November 26, 2026 | 8:00 AM
Location: 333 Center Street, Healdsburg, CA
Start Thanksgiving morning with the annual Healdsburg Turkey Trot, a festive 5K run and walk through downtown. This community tradition welcomes runners, walkers, and families while supporting a local student scholarship.
Merry Healdsburg Tree Lighting & Holiday Night Market
Date: December 4, 2026 | 5:00-9:00 PM
Location: Healdsburg Plaza, Healdsburg, CA
Celebrate the start of the holiday season as Healdsburg Plaza comes alive with festive lights, live music, carriage rides, a holiday night market, and complimentary photos with Santa. A beloved tradition for visitors and locals alike.
Holiday Wine Trail & Market
Date: December 5, 2026
Location: Participating wineries across Northern Sonoma County
Experience a festive day of wine tasting and holiday shopping along the Wine Road. Visit participating wineries, discover locally produced wines, and find gifts for the wine lovers on your list.
Healdsburg Chorus: Winter Illuminations
Date: December 12-13, 2026
Location: Raven Performing Arts Theater, Healdsburg, CA
Enjoy an uplifting holiday concert featuring seasonal favorites, traditional carols, and choral performances. A wonderful way to spend a December afternoon or evening in Healdsburg.
Christmas Jug Band & Shana Morrison
Date: December 18, 2026
Location: Raven Performing Arts Theater, Healdsburg, CA
Add a little music and laughter to your holiday getaway with a lively seasonal performance featuring the Christmas Jug Band and Shana Morrison.
Alexander's Café & Wine Bar
Location: The Lodge at Healdsburg, 1261 Grove Street
Start your morning with freshly brewed coffee, breakfast sandwiches, and pastries, or unwind in the evening with Sonoma County wines and locally inspired small bites without leaving the hotel.
Dry Creek Kitchen
Location: 317 Healdsburg Avenue, Healdsburg
Enjoy an elegant Wine Country dinner featuring seasonal California cuisine and an impressive selection of Sonoma County wines. An inviting choice for a special holiday evening.
Website: Dry Creek Kitchen
The Matheson
Location: 106 Matheson Street, Healdsburg
Celebrate the season with contemporary California cuisine, locally sourced ingredients, and an extensive wine selection at this downtown restaurant near Healdsburg Plaza.
Website: The Matheson
Bravas Bar de Tapas
Location: 420 Center Street, Healdsburg
Gather with friends and family over Spanish-inspired tapas, shareable plates, and handcrafted cocktails in a lively downtown setting.
Website: Stark Restaurants
Healdsburg Farmers Market
Dates: Saturdays through December 19, 2026 | 8:30 AM-12:00 PM
Location: Foley Family Community Pavilion, 3 North Street, Healdsburg
Shop locally grown seasonal produce, fresh flowers, artisan foods, and handcrafted goods at this popular downtown farmers market. It's an ideal stop for experiencing the flavors and traditions of Sonoma County.
Healdsburg Holiday Craft Market
Dates: Select Saturdays in November and December 2026 | 8:30 AM-12:00 PM
Location: Foley Family Community Pavilion, 3 North Street, Healdsburg
Discover unique holiday gifts created by local artists and makers, including handcrafted items and seasonal treasures. Browse the craft market alongside the weekly farmers market for a festive morning of shopping.
Healdsburg Plaza Holiday Shopping
Dates: Throughout November and December
Location: Healdsburg Plaza, Downtown Healdsburg
Explore locally owned boutiques, art galleries, specialty shops, and tasting rooms surrounding Healdsburg Plaza. Find one-of-a-kind gifts, Sonoma County wines, and locally inspired treasures while enjoying the festive downtown atmosphere.
Plaza Gourmet
Location: 108 Matheson Street, Healdsburg
Discover kitchenware, culinary accessories, and Wine Country-inspired gifts at this specialty shop overlooking Healdsburg Plaza. A great stop for holiday shoppers who love cooking and entertaining.
Forager | a modern mercantile
Location: 310 Center Street, Healdsburg
Browse thoughtfully selected home goods, accessories, and distinctive gifts at this modern mercantile in downtown Healdsburg.
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