With fewer crowds, seasonal experiences, and endless romance, the winter season is an ideal time to explore charming Healdsburg. And there’s no better spot to enjoy all of the happenings than Healdsburg Inn on the Plaza. Overlooking the town’s historic central Plaza, this Four Sisters Inns boutique gem has the best location in town, steps from stylish shops, wine tasting rooms, and superb restaurants. Plus, the Alexander and Russian River Valleys are just a short drive away.

Healdsburg Inn on the Plaza guestroom.

For more than 40 years, Four Sisters Inns have invited guests to retreat, indulge, and relax in settings filled with comfort and charm. Offering gracious service and unique amenities, each is a haven for travelers seeking architecture, history, location, and character. 

At Healdsburg Inn on the Plaza, high-ceilinged rooms feature fireplaces, jetted spa tubs, plush bedding, and cozy robes. Stays include a bountiful breakfast buffet and afternoon wine with appetizers. Whether you seek a culinary walking tour, guided vineyard hike, or reservations at a must-try restaurant, the Inn’s complimentary concierge services will help you get the most out of your Healdsburg getaway. 

The New Year brings a wealth of activities and adventures to this increasingly vibrant pocket of Sonoma County. Here are a few of the best: 

Winter WINEland, January 14-15 

At Wine Road’s annual Winter WINEland meet winemakers from 70 wineries and taste limited-production wines and new releases from Alexander Valley Vineyards, Orsi Family Vineyards, Truett Hurst Winery and more. Tickets are available here for $95 per person for the weekend; $75 for Sunday only; and $10 for designated drivers.

Sip & Mandala Dot Painting at Comstock Wines: January 21

Comstock Wines invites you to sip, socialize, and create with a wine flight and a guided lesson painting lesson in Mandala dot paintings on recycled Comstock Wine bottles. $45 per person; reservations can be made here.

Comstock Winery

Dry Creek Vineyard Barrel Tasting: February 11

Deconstruct the rich history and techniques of old vine zinfandel at Dry Creek Vineyard’s barrel tasting event in their cellar room. Taste barrel samples of limited-production wines and enjoy delicious bites. Tickets are $40/pp; purchase here.

Blanc de Blancs & Oyster Pairing at Comstock Wines: February 11-12

Celebrate Valentine’s Day at Comstock Wines oyster and wine pairing created by Executive Ched Jude Affronti. Pairings include 2022 Blanc de Blancs with raw local oysters and 2015 Zinfandel with baked local oysters and barbecue sauce. $40/pp, reservations here.

Costeaux French Bakery

Olive You, Costeaux: February 14

Costeaux French Bakery kicks off its 100-year anniversary with a multi-course dinner showcasing local olives and oils, as well as a Q&A with Don Landis of Don’s Olives and Mary Louise Bucher of Dry Creek Olive Company.

Valentine’s Day Dinner at Dry Creek Kitchen: February 14

Love is on the menu at Charlie Palmer’s Dry Creek Kitchen, located inside Hotel Healdsburg. The  five-course, lovers-inspired dinner features Tsar Nicoulai Caviar panna cotta, warm leek and scallop shell, porcini garganelli pasta with winter truffle, a Liberty duck duo, black angus filet with foie gras and chocolates for dessert. $155/pp; add wine pairing for $90. Reservations here.

Valentine’s Sip ‘n Cycle Tour with Getaway Adventures, February 1-28

Travel through Healdsburg’s picturesque trails on a Getaway Adventures’ e-bike tour stop for wine tastings, and a picnic lunch from Oakville Grocery. $299 pp; more details here.

Dry Creek Peach Excursion: February 28 – March 14

Harmon Guest House partners with Dry Creek Peach to offer this fun excursion led by Dry Creek Peach owners Brian and Gayle Sullivan. Includes a tour of the farm, a tasting of fresh peach bellinis and one bottle of Alley Six Peach Brandy to take home. Guests may elevate their experience with a picnic lunch from Spoonbar. $230 for 2-4 guests. Reservations can be made by emailing [email protected].

Barrel Tasting Weekend, March 3-5

The annual Barrel Tasting Weekend hosted by Wine Road provides the opportunity to learn about the winemaking process directly from the vintners. Tickets  - on sale January 17 - are $85 for early bird weekend; $95 for weekend tickets; $75 for Sunday only; and $10 for designated drivers. More information here.

Alexander Valley Vineyards Wine Dinner, March 18

Family-owned Alexander Valley Vineyards celebrates the release of the CYRUS label with a wine dinner in its 25,000-square-foot underground wine cave. The candlelit dinner includes vintages of CYRUS paired with three courses by chef Tim Gleadall. Tickets are $17 for wine club members and $225 for non-wine club members. Purchase here.

Mushroom Foraging at Montage Healdsburg: Through March 31

Through the end of March, Montage Healdsburg guests can book the Mushroom Foray experience in partnership with Adventure IO. The two-hour experience includes a guided forage and hike, a foraging pocketbook, one bottle of wine, mushroom-themed snacks, and a gift bag. $699; book here.

Portalupi Caviar & Wine Tasting

Caviar & Wine Pairings at Portalupi Wine: Ongoing

Portalupi Wine’s new pairing offers world-renowned caviar from chef Thomas Keller and Shaoching Bishop’s Regiis Ova, paired with Portalupi 2021 Arrossire di Barbera, Methode Champenoise. $64 for 15 grams and $105 for 30 grams; or Portalupi 2020 Barbera, with flavors of dark plum, licorice and fig, priced at $54 for 15 grams and $88 for 30 grams. Book here.