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Honing in on Happiness in Healdsburg

In the heart of Sonoma’s picturesque wine country, charming Healdsburg and surrounds has plenty to offer wine lovers, foodies, and those seeking a delightful urban escape. Its grassy central town square and Mayberry-like downtown contains art galleries, specialty shops, restaurants, and tasting rooms, while top-notch vineyards nearby offer memorable oenological experiences coupled with dining extravaganzas designed to make one’s tastebuds weep with joy.

Those who have visited Healdsburg know that it has created something unique. One that few towns of its size – population 13,000 – have been able to accomplish: maintaining its alluring small-town vibe and natural beauty while nurturing and engaging its inherent appeal to sophisticated travelers.

The Bed

Hanging my hat at The Madrona Hotel was akin to stepping back into a marvelous bygone era. Originally built in 1881 by the Paxton family as a grand estate, its renovations were lovingly completed three years ago. About a mile from downtown Healdsburg and perched atop a winding verdant driveway, The Madrona’s main manor comes into view. Here there are eight rooms, a salon, parlor, both with fireplaces and fine objets d’art. Off to the side, its light-filled Hannah’s Bar is where talented mixologists ply their trade – try the Guava Sour, you can thank me later – and where hot continental breakfasts are served. The main restaurant on the manor’s opposite end has both indoor and al fresco dining.

Across the way, the carriage house has another nine rooms and spread on the property amid orange trees and a lovely pool are six bungalows and an owner’s loft. San Francisco’s Dolby Chadwick Gallery has placed numerous intriguing pieces of art throughout the property, most of which are available for purchase.

Staying in room M2, it boasted 15-foot ceilings, an antique-tiled gas fireplace with a period wood mantle, a large gray velvet, tufted sofa and Carrera marble topped coffee table. Fresh, pungent oranges from the property’s orchard were on a cutting board making me smile. 

The king-sized bed had high-count cotton sheets, and a padded headboard. Mornings were pleasurable as the bar area had a Nespresso machine and a thoughtfully stocked refrigerator. Small glass decanters containing half-and-half and almond milk, as well as whole lemon and tangerine to complement its good collection of spirits, including Botanist dry gin and Madre Mezcal, all made the difference between a good stay and a great one. Enjoying a morning coffee or afternoon cocktail on my room’s massive outdoor patio overlooking nearby vineyards was priceless. 

The large bathroom had marvelous, heated black-and-white tiled floors and dreamy cotton Kassatex NY robes. The two-person shower had both a European handheld and standard shower head with environmentally friendly Flamingo Estate amenities.  Simply put, The Madrona is one of those rare properties where geography, architectural design, art and thoughtful, hospitable staff are combined, creating a true gem.

Meals and Grapes

An easy 10-minute drive from the Charles M. Shultz Sonoma County Airport decorated with the comic’s iconic Peanuts mosaics, sculptures and graphic artwork, is The Montage Hotel that opened in early 2021. Set on 258 acres, Montage’s Hazel Hill restaurant overlooks some of its 15-acres under vine and is a relaxing lunch spot to commence one’s withdrawal from city life. Hazelnuts are planted here, along with both black and white truffle spores, and several bee hives. You may also see Beau, the adorable Italian truffle hunting pooch on property. Or if visiting in the fall, Montage’s gang of goats who are duly employed as sure-footed gardening governors.

In downtown Healdsburg, The Matheson restaurant has a decorative, yet functioning wine wall; perfect for commitment phobic guests to sample and enjoy several wines. Lucky for me, I was able to fully embrace my inner oenological commitment aversion as I was joined for dinner by Copain Wine’s affable winemaker Ryan Zepaltas who arrived bearing a cache of his Chardonnays, Pinot Noirs, and a Cabernet Franc.

The milk bread croutons gracing Chef Dustin Valette’s Ceasar salad alone is worth a trip to The Matheson. The Wagyu flat iron will make clear that becoming a vegan isn’t an option, while the chocolate pavé is proof that Chocoholics should consider forming their own political party. Copain’s wines delightfully complimented the meal, and standouts were its aromatic, dry white 2023 Daybreak, its fruit forward, bright 2021 Sealift Pinot Noir, and its rustic, peppery 2021Taylor Peak Cabernet Franc. I was thrilled to learn that this fall, Copain will be releasing a sparkling wine from its 2018 vintage.

Another evening, I had dinner al fresco at The Madrona and admittedly, making a selection was challenging as Executive Chef Patrick Tafoya’s creative menu is a slightly jaded diner’s delight. Finally, I settled on the Madrona salad that was so fresh it was surely in the ground that morning. The grilled local black cod with caviar cream, fennel and kawa was satisfying and superb. While I had no room for dessert, my arm was naturally twisted and the chocolate whiskey cremeux was decadent.

The Finds

If ever there was a marriage made in wine heaven, it would have to be what became Vérité Wines and their marvelous Bordeaux blends. Established in 1998, it was the culmination of visionary Jess Jackson’s aspiration to create great wines, and his then budding friendship with French Vigneron Pierre Seillan and his utterly charming wife Monique. Though Seillan then spoke almost no English, an intense bond was born, and the rest is grape-loving history.

The result of this wedded bliss became the Vérité trifecta: the full-bodied La Joie, 84-percent Cabernet Sauvignon, the velvety La Muse, 90-percent Merlot, and the refined Le Désir, 83-percent Cabernet Franc, all of which arise from regional Vérité micro-crus and convey what Seillan calls, the “right of the soil.”

Last May the Vérité Estate’s new space opened about 20-minutes from downtown Healdsburg. It was worth the Covid-delay as the Estate is a beautiful, light-filled expanse reflecting European sensitivity coupled with California charm. As the new barrel chai has strategically placed windows near the arched ceiling, it too is light-filled and design dramatic. 

The Estate has several tasting experiences. The pièce de résistance is its Library Food & Wine Pairing Experience, where Chef de Cuisine Justin Wangler showcases his inspired culinary creativity taking into account seasonal and local sources. Delighting in delectable seafood bouillabaisse, perfect potato gnocci, tender strip steak, and a red wine poached pear with mascarpone so marvelous, I never noticed no chocolate was involved. Paired alongside six Vérité wines – picking a favorite was futile, they were all excellent – the experience induced bliss rendering it entirely possible that my next clan member will be named Pierre Justin.

With Hélène Seillan continuing her father’s vision, the future of Vérité is bright, paying homage to their shared passion while taking into account changes in climate, grapes, and the terroir the Seillans’ clearly love. 

In downtown Healdsburg, you’ll want to pop into the Hartford Family Winery tasting room. Founded in 1994 by former lawyers Don and Jenny Hartford, it has 125 Acres under vine, and is focused on single vineyard Pinot Noirs, Chardonnays, and Old Vine Zinfandel with extreme personalities. I enjoyed their 2022 Russian River Valley Chardonnay with its citrus leanings and higher acidity. The 2021Seascape Vineyard Pinot Noir was both earthy and berry forward.

Hartford noted that, “People graduate to Pinot Noirs. It’s not love at first sight. It’s a textural kind of romance with Pinots that are silky, satiny, and sexy.” I agree, becoming a Pinot fan somewhat later in life. Besides, Hartford should know all about love at first sight since he immediately fell in love with Jenny on their first day of law school many moons ago. 

Downtown Healdsburg’s Yasuko has Japanese textiles and unique vintage articles, while artist-owned Bradford Brenner Gallery has some excellent figurative and abstract pieces. For a taste of history, head to Healdsburg Museum. In a neoclassical revival building, its permanent collection has native American baskets, textiles, and military artifacts. And when ice cream calls, head to Noble Folk Ice Cream & Pie Bar for small batch staple flavors; chocolate anyone? Or creative flavors like Thai Tea.

The Lesson Learned

Local Healdsburg firm, Thurow Wealth Management, uses as its moniker, “To live a rich life, invest in memories.” With lovely accommodations, inspired chefs, and oenological magic made here daily by people clearly passionate about wine, a visit to Healdsburg is certainly a great place to start creating those unforgettable memories.

Julie L. Kessler is a journalist, attorney, and the author of the award-winning memoir: “Fifty-Fifty, The Clarity of Hindsight.” Her work has appeared in several major publications around the world, including The LA Times, The SF Examiner, The Asia Times, The Jerusalem Post, and The Honolulu Star-Advertiser, among many others. She can be reached at

Julie L. Kessler

Written by Julie L. Kessler

Julie L. Kessler is Money Inc's Senior Travel & Luxury Editor and writes for several major media outlets in the U.S. and overseas. She is also an attorney and legal columnist and the author of the award-winning book "Fifty-Fifty: The Clarity of Hindsight." She can be reached at

Read more posts by Julie L. Kessler

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