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Welcome to Healdsburg, a picturesque town just north of San Francisco, California, where the holiday season comes alive with a touch of magic. If you’re seeking the perfect winter getaway filled with festive charm, look no further than Merry Healdsburg Weekend. This enchanting event promises a delightful blend of holiday cheer, family activities, and the cozy ambiance of a winter wonderland right in downtown Healdsburg.

The festivities begin on Friday evening, December 1st, from 4 pm to 9:30 pm. Gather your loved ones and head to the Plaza for a heartwarming experience, including a tree lighting ceremony featuring a 45-ft decorated tree, a visit from Santa Claus, live music, a holiday night market, and much more.

All Weekend Long:

  • Holiday Sip & Shop Saturday, December 2 | 4 – 7 pm: Taste your way through more than 15 downtown Healdsburg stops, shop for the holidays, and savor award-winning wine. This year, food vendors offer delicious bites along the way, and you can play Healdsburg Holiday Bingo for a chance to win prizes.

  • Holiday Tea at Dry Creek Kitchen December 2-23, 2023 | Saturdays + Sundays | 1 – 2:30 pm: Enjoy a festive afternoon at Hotel Healdsburg with holiday decor, live piano music, custom blend teas, and classic cocktails. Indulge in house-made pastries, finger sandwiches, and holiday fare from Dry Creek Kitchen.

  • Healdsburg Jazz Holiday Swingin’ Dance Party & Concert Saturday, December 2 | 6 – 9 pm: Enjoy a special Holiday Swingin’ Dance Party & Concert featuring saxophonist Jules Broussard, vocalists Tiffany Austin and Derek Evans, and the Marcus Shelby Trio. Dance class, concert, and dance party from 6 pm onwards.

  • Breakfast with Santa at Costeaux French Bakery Every Saturday in December | 9 – 11 am: Children can meet Santa, share their wish lists, and take a digital photo at Costeaux French Bakery. Explore the Nutcracker collection and get help with holiday planning and catering.

  • AQUA NETT at Coyote Sonoma Saturday, December 2, 2023 | 8 – 11 pm: Join the Hair Force for an 80’s Party Rock night with Aqua Nett at Coyote Sonoma. Rock out to classics from Guns N’ Roses, Billy Idol, Def Leppard, Bon Jovi, Journey, and more.

  • Victorian Carolers Every Saturday in December | 3:30 – 5:30 pm: Healdsburg will have Victorian carolers roaming downtown to spread holiday cheer.

Where to Stay:

For your Merry Healdsburg adventure, consider Calderwood Inn or Grape Leaf Inn. The Calderwood Inn, a beautifully restored Victorian mansion, offers a charming ambiance, personalized service, delicious breakfast, and a prime location near Healdsburg’s Plaza.

Meanwhile, the Grape Leaf Inn, known for its luxurious boutique-style accommodations, provides a tranquil oasis with private gardens, evening wine and cheese receptions, and proximity to renowned wineries. Both inns offer warm hospitality and a cozy home base to enhance your Merry Healdsburg experience.


Day 1: Festive Delights and Family Fun

Begin your day with a scenic drive into town, immersing yourself in Healdsburg’s stunning surroundings. Your first stop should be Black Oak Coffee, a local favorite known for its signature drinks. Take a moment to savor the rich flavors and get energized for the day ahead.


Head over to Costeaux French Bakery, where you can indulge in their renowned pastries. Be sure to try their most famous item—it’s a delectable treat you won’t want to miss.

For lunch, make your way to Lo and Behold, where a delightful meal awaits. The stage is set for a memorable dining experience that will fuel your afternoon adventures, complete with an array of craft cocktails to elevate your dining experience.

As the sun sets and the town transforms into a winter wonderland, join the community at the tree-lighting ceremony. Capture the magic with photos alongside Santa, and savor hot chocolate and delectable desserts from local vendors. With plenty of family activities, this is a time to create special memories with your kids.

After a day of excitement, return to your cozy hotel room at Calderwood Inn or Grape Leaf Inn. Unwind and recharge for another day of festive fun.

Day 2: Exploring Healdsburg’s Charms

Embrace the leisurely pace of Healdsburg by starting your day with a tranquil walk through the Plaza. Take in the beauty of the town and its holiday decorations.

Explore the many local boutiques that adorn the Plaza. This is also an excellent opportunity to get a head start on your holiday shopping at the Holiday Sip & Shop. You’ll find unique items and gifts that make perfect souvenirs or presents for loved ones and maybe even a little treat for yourself. Don’t miss the Paul Mahder Gallery, where captivating artistry awaits.

Satisfy your appetite with a visit to Pizzando, a local favorite known for its delicious pizza. If your sweet tooth beckons, make a beeline for Noble Folk Ice Cream after lunch. Their delightful ice cream flavors are a must-try.

Healdsburg is renowned for its wineries and tasting rooms. Stop by one of the many tasting rooms on the Plaza for a delightful journey for your taste buds. Consider options such as LIOCO Wine Tasting Room, Thumbprint Cellars, Siduri Wine Bar & Tasting Lounge, Marine Layer Wines, and more.

No trip to Healdsburg is complete without a visit to Barndiva. End your night with a cozy evening next to a fire pit, sipping on a glass of local wine and savoring the magic of Healdsburg. Plan to stay happy this holiday season by booking your stay to Healdsburg today!