Make plans now to kick off your holidays in the heart of California's wine country.

Written by Elliott Greene

'Twas the First of December

in Healdsburg, C-A.

All the citizens were stirring

for the holiday kickoff this day.

The vendors were staged

round the square with care

Knowing that soon, customers (and St. Nicholas)

soon would be there.

A steady drizzle couldn't dampen the cheer,

as a countdown progressed and the tree lights appeared

While carolers' dulcet tones tickled the ears,

the clip-clop of hooves announced that Santa was near.

The children's eyes widened as the sleigh came into sight,

capping off what ended up being a very good night.

Charming any time of year, the heart of historic Healdsburg—established in the mid-1800s by Ohio native and gold prospector Harmon Heald—is its square. An impressive array of top-notch restaurants, up-scale lodging, tasting rooms, boutiques, and art and jewelry galleries pack the streets facing the central plaza. During the holidays, the scene is made even more magical via Merry Healdsburg Tree Lighting, hosted by the Healdsburg Chamber of Commerce and Stay Healdsburg (stayhealdsburg.com). Lucky guests in rooms at the front of the 56-room Hotel Healdsburg (hotelhealdsburg.com), located on the western edge of the square, have a prime view of the massive Christmas tree and can enjoy its twinkling lights throughout the season from their Juliette balcony.

This December will mark the fourth-annual Merry Healdsburg event, which includes a Holiday Market, carriage rides, live music, and photos with Santa. The Christmas cheer continues the day after the tree lighting with a Holiday Sip & Shop, during which nearly two dozen participating local shops offer ticket holders extended hours and tastings of the area's award-winning wines. A Holiday Tea at Charlie Palmer's Dry Creek Kitchen in Hotel Healdsburg (drycreekkitchen.com) offers the opportunity to enjoy a festive afternoon out with friends and family of all ages. The elegant afternoon unfolds with piano accompaniment, custom-blend teas, and picture-perfect sweet and savory bites. I don't know what magical spell was cast or bribes made, but we were absolutely enrapt by the number of children in their Sunday best acting their best, which added another level of enchantment.

Healdsburg is perfectly positioned amid the Dry Creek, Russian River, and Alexander Valley AVAs, and the area around the square is home to more than two dozen tasting rooms. Opened last summer, the elegant tasting room of Ernest Vineyards (ernestvineyards.com), designed by LA-based interior designer Matt O'Dorisio, is a fitting pairing for tasting their site-specific wines. Co-founder Erin Brooks and winemaker Joseph Ryan put a premium on vine health, employing organic and regenerative farming methods on their 35 acres of vineyards spread across several distinct cool-climate sites on the Sonoma Coast. Brooks, a Texas native, exited a fast-lane career in tech for a bumpier but far more scenic backroad adventure as a self-taught vintner. Her analytic and technical skills have not fallen by the wayside, as her company boasts one of Wine Country's most sophisticated production facilities, which she makes available to fellow small producers.

A voracious reader with a nearly insatiable quest for intel on topics in which she's interested, Brooks said that she went from a wine consumer to an enthusiast and now a zealot. She began by tasting lots and lots of wine up and down the Sonoma Coast to define her palette, cold-calling growers, imploring them to sell her grapes, and seeking mentorships from respected vintners and winemakers. While she always felt confident that the "dominoes would eventually fall into place," Brooks says the training wheels didn't come off until she met Ryan. "We just feathered together like two siblings." Ryan, an Iowa native and fellow chardonnay champion, worked in Burgundy and Sonoma County. He executes Brooks' vision for "Burgundian-style wines offering bright acid, low alcohol, minimal oak, and balanced flavor."

When we weren't sipping or shopping—French textiles at Maison Smith (maisonsmith.us), unique men's and women's clothing and accessories at Susan Graf Limited (susangraf.com), beautiful tableware from Forager (foragerhealdsburg.com), and all the pretty things for home and her at Anthem (anthemsf.online), we were eating, a lot. Food always tastes fresher to me in California. We had no regrets about making quick work of warm Belfiore burrata and fluffy-crust pizza drizzled with truffle oil at the lively PizZando (pizzandohealdsburg.com), located near the entrance of Hotel Healdsburg.

My better half, a committed carnivore, was skeptical about dinner at a one-hundred-percent plant-based restaurant. By the end of our meal at Little Saint (littlesainthealdsburg.com), he didn't miss meat for a moment. Designed as a community gathering place and creative haven, the sprawling two-story establishment encompasses a restaurant, coffee bar, wine lounge, cocktail bar, gourmet grab-and-go, and music venue outfitted in bohemian-luxe style.

We were thrilled to see that the carrot tahini, cultured carrot spread with tomato chutney, and green lentil hummus we enjoyed as part of a tasting at nearby Marine Layer Wines several years earlier were among the available starters. Just as good as we remembered, we begged the chef to release a cookbook so we could recreate them at home, along with our entrees: a vegan winter squash lasagna with cashew ricotta and a Maitake mushroom au poivre with brandy cream.

Little Saint's inventive and impressive cocktail menu offers a respite for wine-weary imbibers. At the same time, their conscientious wine list highlights winemakers who are aligned with their business ethos of treading lightly on the earth.

Nirvana for oenophiles, the wine wall at The Matheson offers 88 wines by the dram or glass. While it's obviously heavy on Russian River Valley offerings, there are also popular European classics and several under-the-radar surprises for adventurous imbibers. Similar to Little Saint, the three-story building is home to distinct concepts. Under the leadership of chef/owner Dustin Valette, ambitiousness doesn't hamper ambiance or experience as we enjoyed a delightful seasonally focused dinner in the bustling space, packed to the gills with beautiful people.

A fun spot for breakfast or lunch, don't miss what is likely the largest assemblage of nutcrackers you're sure to spy in one place at Costeaux French Bakery (costeaux.com). From November through mid-January, the century-old institution displays whimsical wooden characters of all sizes, which Will Seppi, the current president and CEO of the bakery, refers to as their "Nutcracker Orphanage."

We capped our Healdsburg holiday a short drive from the square at The Montage (montage.com/Healdsburg), a 258-acre retreat where the 130 modern bungalow-style guestrooms are surrounded by steeply sloped vine-covered hills and stately moss-covered California oak trees. The Montage's sprawling spa boasts one of my favorite fitness studios with a stunning view of their adults-only zero-edge outdoor pool (for a fun off-property workout, book an E-Bike and grab a winery map from Gateway Adventures— getawayadventures.com—to embark on self-guided tour of the area). The refined setting at Hazel Hill, the resort's all-day dining destination, mirrors the terroir-to-table cuisine, quintessentially California with a touch of je ne sais quois.

Elegantly outfitted for the season, the indulgent escape offers tree and menorah lighting ceremonies and other special activities, including a wreath-making workshop. While the décor at The Montage isn't at all saccharine, its daily afternoon hot chocolate station, with a dizzying array of confectionery accouterments, would definitely satiate even Santa's sweet tooth.

Ho Ho Healdsburg