Sonoma County’s Healdsburg nestles in a curve of the Russian River in a northern section of the county. Founded in 1857, Healdsburg boasts a central plaza that offers a shady respite during the day’s heat and lighted paths at night.

We arrived at the Charles Schultz Airport in Santa Rosa and, taking a Lyft to the car rental company in downtown Santa Rosa, picked up our vehicle. Thirty minutes later, we moved into our room at the Dry Creek Inn for the first three days of a 10-day trip. It gave us the best possible spot to access the nearby towns of Sebastopol and Geyserville.

Downtown Healdsburg

Healdsburg’s downtown district is a collection of art galleries, shops, restaurants, tasting rooms, and the marvelous Costeaux French Bakery. The bakery has anchored the town square for 102 years and opens for breakfast and lunch Wednesdays through Sundays. Costeaux has a mind-boggling array of baked treats to tempt even the most adamant “I don’t eat breakfast”-er.

Costeaux Bakery prides itself on its bread. Bakers shape breads by hand, allowing them to ferment for up to two days. Then, the loaves are baked in a hearth oven imported from Italy. The bread makes the sandwich, and Costeaux serves many made-to-order items, like Monte Cristo and Pain Perdu, a mouth-watering concoction on the bakery’s famous cinnamon walnut bread, topped with seasonal fruit, whipped mascarpone, and Vermont maple syrup. They have other items to delight your taste buds, such as Deep Dish Quiche, Farro Salad, and Pomme Frites.

And then there are the cookies. Oh, my goodness! The bakery cases overflowed with cookies that called my name. The pastry chefs make French Macarons daily—these have been named the best cookie at the Sonoma County Harvest Fair. I had a couple, and let me tell you, those judges were right.

Healdsburg Plaza

The historic plaza in Healdsburg was established in the mid-1800s, by Harmon Heald. Heald was an Ohio native who came west during the gold rush. Summer months find the plaza filled with food vendors and music events.

As you stroll the streets of Healdsburg, you find tasting rooms tucked into tiny spaces betwixt and between restaurants and shops. Noble Folk Ice Cream and Pie Bar called to us as we searched the plaza for dinner. Could you resist mango sorbet topped with a mango macaron? You know what they say: Life’s short; eat dessert first.

We wandered into Stressed Vines on the way to dinner, mainly because a cute dog was looking at us over the counter. But, then we decided we could have two desserts first (you do realize what that spells backwards, don’t you?) Only opened since mid-July, the shop specializes in stocking small production wines from Sonoma and Napa County’s best vineyards, and pouring them by the glass. We enjoyed the 2021 Reynoso Vineyards Cabernet Sauvignon from the Alexander Valley.

Just down the block is the first tasting room we visited in Sonoma County (and even California). With that distinction, Spicy Vines had to live up to some high expectations.

Wine Country Surrounds Healdsburg

Healdsburg sits at the crossroads of three AVAs (American Viticultural Area)—the Alexander Valley, Dry Creek Valley, and Russian River Valley. With three AVAs to draw from, we were expecting wonderful things. Sonoma County did not disappoint.

Spicy Vines

A visit to the Spicy Vines tasting room in Healdsburg is unforgettable. Our tasting room host, Declan Hackett, has a love for community theater that shines; his personality is as big as the flavorful wines! He is at home behind the bar of the lounge-like tasting room, which is comfortably fitted with couches, tables, art, and live music on Saturdays,

Declan’s dad, Doug Hackett is the talented winemaker. With a background of nearly 30 years in Sonoma and Mendocino County vineyards, he joined wife Crystalyn at Spicy Vines. She founded the winery in 2011, inspired by her love of old-world wines, especially a spiced wine from ancient Roman and Egyptian civilizations. The two and their family are producing wines from some of the finest vineyards in the area.

Some of the wines are named for family members, and Declan’s Delight Pinot Noir, was a true delight! It earned a smiley face AND a star on my tasting sheet…and a special place in my shopping bag! He had some great quotable comments, too. This guy can keep a party going!

“Sex and candy in a bottle” is how Declan described the Zinfandel made from the oldest producing Croatian vines in Russian River. That is probably the best possible description of that wine.

Describing Ellie Rosé, Declan declares, “It tastes like you’re floating down the Russian River, while sucking on a blue raspberry Jolly Rancher.” (I told you he has a flair.)

Longboard Vineyards

Longboard Vineyard is owned and operated by Oded, an Israeli surfer who came to California for the surfing and wine school degrees from the University of California at Davis and never left. Diesel usually accompanies the winemaker/owner, following close on his heels. The décor at Longboard is, true to its name, colorful long surfboards.

Jody stayed busy with several tables of wine lovers tasting Longboard’s specialties. We tasted and enjoyed many lovely wines, from sparkling to white to pink. Then, we moved on to wines inspired by the regions of Burgundy, Bordeaux, and Rhone. I like a winemaker who loves it all.

Oded grows 40% of his grapes on 7 acres. The tasting room has a tempting list of bites available. I still regret not having room for the Braised Short Rib & Fig Sonoma Hand Pie. Oded says his wines are “thoughtfully balanced for free spirits.” Sounds a lot like surfing.

Dutton Estate Winery

The Wine and Halloween Candy Tasting at Dutton Estate Winery made us feel extra special! We had a personalized tasting list with our names and the date at the top to accompany our tiny “coffin” filled with candies. We started with their Blushing Sisters Rosé of Pinot Noir paired with a Watermelon Sour. I know that sounds strange, but it hit a delightful balance between sweet and sour…and who doesn’t love watermelon?

Next came My Father’s Vineyard Syrah alongside a Peppermint Patty. The dark fruits of the syrah complimented the coolness of the candy and added a layer of coffee to its dark chocolate coating.

Dutton Chardonnay washed down a piece of Mango Licorice, while the Thomas Road Vineyard Pinot Noir was served with a dark chocolate peanut butter cup. Can you spell d-i-v-i-n-e? But my favorite, saved for last, was the Manzana Vineyard Pinot Noir melded with a Raspberry Dark Chocolate drop. We left Dutton’s swearing there would be no dessert after dinner that night. (Do you lie to yourself about food, too?)

Alexander Valley Vineyards

One morning is a good start for a visit to the family-owned Alexander Valley Vineyards. The vineyard property has an incredible history, offering vineyard hikes, cave tours, and tastings. There is so much to do at Alexander Valley that one morning quickly becomes an entire day of walking, exploring, and tasting.

Alexander Valley Vineyards hides Sonoma’s largest underground wine cave. Book a cave tour and taste wine straight from the barrel. The vineyard also holds cookie and wine tastings and the opportunity to sample local artisan cheeses paired with wines. You can hike, take in the views, and then enjoy lunch on a covered porch.

Pedro made the adventure fun. He poured our first glass of wine in the tasting room as he loaded bottles into his insulated shoulder bag and began telling the vineyard’s story. The vineyard is on property once owned by valley founder Cyrus Alexander.

We tasted wines in the vines and learned valley history. We sipped Gewűrz, Chardonnay, a red blend, and Cabernet Sauvignon. Saving the highlight for our peek into the adobe home he built, we toasted the valley founder with his namesake wine, Cyrus, a luscious blend of Cabernet Sauvignon, Merlot, and Cabernet Franc, with just enough Malbec and Petite Verdot added to pique our taste buds.

A Place Filled With History and Heart

Cyrus Alexander built his adobe home in this valley before 1845. The adobe structure was restored in 1965 and is still used for special winery events. His second home was destroyed by the 1906 earthquake and replaced with the Victorian house that still stands. Only two families, the Alexanders and the Wetzels, have occupied the land and the home.

The Alexander Valley Schoolhouse, built in 1868, was half a mile away. Preservation efforts saw the school moved to a hill overlooking the vineyards and restored in the early 1970s. The schoolhouse appears on the Alexander School Reserve wine label.

Members of the Alexander and Wetzel families rest in peace in a private hillside cemetery. Cyrus Alexander called the land it overlooks the “brightest and best in the world.”

Francis Ford Coppola Winery

The Francis Ford Coppola Winery is a must-see winery located in a building filled with movie memorabilia. You can enjoy food and wine (over 40 wines are produced on-site from sustainably grown grapes). Rustic, a restaurant with indoor and terrace seating, is detailed below. As a bonus, if you have good timing, there is music, dancing, and various performances on winery grounds. You’re even encouraged to dip into one of the two fabulous swimming pools.

Visitors can enjoy the Wine & Cheese Experience on the shaded patio. Generous pours of wine accent tastes of treats like Marin French Cheese Company’s Petite Crème and Fig & Olive Spread, which paired perfectly with the 2021 Eleanor. Eleanor, a bold red wine, is named to honor Coppola’s wife of fifty years. It blends near-equal parts of Cabernet Sauvignon, Syrah, and Petite Sirah. The meat-lover in me wanted to hoard this glass for a rare filet mignon.

Pech Merle Winery

We found the Pech Merle Winery tasting room in the heart of downtown Geyserville. A ski lift was installed in the tasting room for Wine Road’s annual Winter WINELand event and was an outstanding hit with visitors; it’s been there ever since (making this officially the cutest tasting room ever.) Another unique feature of the Pech Merle tasting room is Yappy Hour, where you can enjoy Pups & Pinot.

Pech Merle (pesh-mel) translates to “cave under the hill.” It is family-owned and operated, and its nine varietals have amassed two hundred medals. Jenna poured wines ranging from a Brut Rosé de Syrah to Lake County Sauvignon Blanc, Russian River Chardonnay, Alexander Valley Cabernet Franc, and the Linea, a dreamy Cabernet. Linea combines the best cabernet sauvignons from Alexander and Knights Valley AVAs. The charcuterie platter had cured meats, local veggies, and local and imported cheeses, so there was something to pair with each wine.

Trattore Farms and Winery

Perched 400 feet above the Dry Creek Valley, on the highest ridge, the forty-acre Trattore Farms and Winery grows grapes and olive trees! Go in for a tasting, a class, a concert, or a glass—it’s up to you to decide what will make your visit perfect. You can go just for the view.

The winery has a variety of tastings and tours, so you can learn some history and get the inside scoop on sustainable farm programs. You can also visit the wine cellar and the olive mill, then finish off your tour by tasting their products in the tasting room while you admire the farm’s tractor.

Our wine and oil tastings on the terrace were delicious and fun—more like a party on a gorgeous fall day. The Mourvèdre was one of the first vines planted on the estate, and it ripens slowly, meaning it is the last grape harvested. The final product we tasted had hints of cinnamon, clove, cocoa, and a light violet finish—yum—what’s not to love?

The climate of this farm is similar to France’s Côtes du Rhône region, so growing Grenache, Syrah, Mourvèdre, Viognier, and Cinsault makes sense. They also grow Dry Creek Valley’s best-known (and maybe best-loved) grape, the Zinfandel.

Joe, Trattore’s General Manager, shared insider information about farming techniques. One that stood out and makes so much sense is the old-world technique called “field-blending.” That means the selected varietal rows are held until the aggregate ripeness is perfect. Then, harvested grapes are combined in the field and sent to fermentation.

Olive Oil Tasting

Yes, olive oil tastings are a “thing,” and we tried it all. There are traditional olive oils and co-milled olive oils, which blend the farm’s olives with other local products. Some oils are co-milled with Meyer Lemons, Persian Limes, Valencia Oranges, Basil leaves, or fresh Jalapeños.

The mild olive oil produced at the farm is a three-orchard blend of Spanish and Italian olives. The Healdsburg Blend is a medium-weight oil made mostly of Italian Tuscan olives, with some Spanish Arbequina olives added.

The medium Spanish Table Oil is a mixture of Mission, Manzanilla, and Arbequina green olives with a slightly peppery finish. The farm also produces vinegars, and their pomegranate vinegar with fig balsamic will wake up any salad.

La Prenda Wines

La Prenda Wines has a tasting room where they share La Prenda and 95476 wines (95467 is the Sonoma Valley zip code.) They had a delightful list of small bites, but coming in between lunch and dinner, we only drooled over offerings. They have Crème de Fromage (from the Epicurean Connection, where we learned to make cheese) served with grapefruit rosemary jam and a traditional Italian-style salame plate with black truffle and spices. On the next visit, we’ll arrive hungry.

With Janet’s expert guidance, we tried the 95467 label’s 2021 Pétillant-Naturel, a blend of Chardonnay and Pinot Noir. Then we moved on to a Chardonnay, a red blend, and a Cabernet Sauvignon. There was also a Pinot Noir, which had a surprising cap gun odor and was one of my favorite tastes, with its slightly smoky lingering aftertaste.

La Prenda owners say Sonoma County’s Mediterranean-like climate provides just the right amount of heat and cold, without extremes on either end, that create the conditions to grow the perfect grape.

DaVero Farms & Winery

Dereck took charge of us at DaVero Farms & Winery, leading us on a Discover the Farm tour before we settled in for the highlight of the visit—the tasting. The tour led us along picturesque paths in the farm-to-table garden, allowing for a few extra tastes, like the ripe figs. We also visited the lazy pigs, which are very popular with visitors.

The Dry Creek Valley farm boasts over 14 varieties of Italian grapes, which produce a bounty of wines. One of my favorites was Trovato, which has a big nose but is a light wine from family vineyards in Mendocino. We paired it with farm cheese and plum jam.

Another wine we all agreed on was Impossible, a blend of Montepulciano, Sagrantino, and Nebbiolo, all grown in the Dry Creek Valley and served with goat and sheep milk cheese.

Leo Steen Winery

Eclectic winemaker Leo Hansen was born and raised in Denmark. He is the son of a chef, so food and wine have always been a passionate part of his life. You may find him hanging around The Drink, chatting with customers, but he’s hard at work behind the scenes most days. On Friday, there is a Happy Hour from 4-6 pm.

Leo Steen Wines specializes in making natural wines from organic vineyards found along the coastline of California. Those we tasted included his new creation, 2022 Bubbles of Steen, a sparkling Chenin Blanc that put happy smiles on our faces. Then we moved on to the 2023 Rosé of Grenache and the 2023 “The Steen” Chenin Blanc.

Next, we enjoyed the Casa Verde Red, a Grenache, and, saving the best for last, we savored a Russian River Valley 2021 Pinot Noir.

Williamson Wines

In the middle of downtown Healdsburg, Williamson Wines offers seasonal tapa creations of Chef Colin Curtis paired with winemaker Bill Williamson’s best natural wines. The wine and food pairing we had at Bill’s Cellar was the Icon Tasting.

Russell served us an array of culinary delights and poured the ideal wine with each course. He described each dish, and he had the answers as we peppered him with questions. First, we noshed on a Coconut Thai Green Shrimp Curry, washing it down with Gertie Gewűrztraminer. We devoured several other courses, including a Jerk Salmon Taco with a pink rosé. We finished the day with Red Velvet Crumble Cheesecake and Arouse Melangé, a Bordeaux blend.

You can ask for a Bordeaux, Rhone, or Reserve Tasting if you are most interested in specific varietals.

Stubbs Winery

Now, I don’t want to mislead you since Stubbs Winery is in Marin County. Still, it is only thirty minutes from Healdsburg, near Petaluma. We worked the route into our travel plans one afternoon and were glad we did.

The small family ranch and vineyard are hidden between steep hills, offering a breathtaking view at sunset. Stubbs uses organic and sustainable farming methods. The winery collects rainwater in a reservoir for watering. Many world-class California restaurants serve Stubbs wines, and the winery will happily ship wines to your door.

Stubbs Winery creates estate-grown Chardonnay and Pinot Noir wines that delightfully blend the grapes of coastal California with Burgundian qualities. The owners were traveling in Europe but graciously arranged for their friend Becky to meet us for a late afternoon tasting.

Places to Eat in Healdsburg

To rewrite Julie Andrew’s classic song, “Scarlet sunsets o’er water and dinners on rooftops…these are a few of my favorite things!” Healdsburg has many places to eat, and a surprising number are on rooftops. Here are two favorite rooftops and other exceptional places that fed us in Healdsburg.

Roof 106 at The Matheson

The Matheson is a downtown farm-to-table restaurant with a rooftop cocktail lounge and outside dining areas among the treetops. There are fire pits for cool evenings. Concoctions at the gleaming copper bar include fruits, herbs, and flower blossoms to create memorable handcrafted cocktails. The Roof One-Oh-Spritz was as delicious as it was colorful—a blend of Aperol, Campari, Prosecco, rosé, and citrus hints.

The food at Roof 106 was memorable, too, particularly the Spicy Pork Belly Bites, served with butternut-lemon puree and pickled red cabbage. The Whole Burrata with Sourdough Flatbread arrived dusted with black truffles, porcini mushrooms, and candied hazelnuts drizzled with honey.

For those with heartier appetites or dining with friends, the Rooftop turns out a variety of pizzas from their wood-fired oven. A House Cured Pork Belly Pizza fit the bill for our hungry trio.

You would think all those foods would fill up anyone, but you’d be wrong. We still fit in a light, airy, lemony concoction heaped with whipped cream—split three ways.

Rustic — at Francis Ford Coppola Winery

Rustic has both indoor and patio seating. With a breathtaking view of the Alexander Valley from the terrace, where to sit was an easy decision. We arrived after a long morning of hiking the Alexander Valley hills and exploring wine storage caves outside Healdsburg. You know what that means: we arrived ravenous. The first thing our server, Rene, delivered to our table was a fully loaded cheese board with some cured meat, fruits, nuts, and crackers.

Knowing a full meal was coming, we tried not to fill up on cheese. *grin* A giant bowl filled with zucchini fries arrived. We dived in and wished for larger bellies. In preparation for the main courses, we shared fries with the tables near us (who were all drooling as they watched us eat).

Sharing two entrees, we had a perfectly cooked steak with creamed avocado and roasted peppers and a grilled salmon served over gnocchi.

We ended the meal with the day’s special apple version of a Stone Fruit Crostata. Rustic’s house-made vanilla gelato and a salted caramel sauce topped the warm, fall-flavored apple pie.

Campanella Kitchen

Tucked away in Sebastopol, only thirty minutes from the Dry Creek Inn, is a wonderful treat, Campanella Kitchen. We had a fantastic evening at Campanella, starting with a picture-perfect Signora Bianca cocktail of Meyer Lemon and Verbena Syrup.

The Little Gems salad with Arancini (beef ragu, peas, and mozzarella balls) came quickly; then we moved on to the Seafood Salad. The arancini were a delightful surprise, leaving me thinking that an entire bowl of them wouldn’t be too many. A plate piled high with pillow-soft potato gnocchi smothered with ragu bolognese, roasted tomatoes, and Parmigiano Reggiano arrived next.

Dessert is always nearly impossible to narrow down to one item, so we had the night’s special, an Apple Torte and their Rainbow Cookies. They were both delicious, but a spoon of salted caramel with a bite of apple was perfection.

Harmon Guest House Rooftop Restaurant

The Rooftop terrace lets you rise above it all and soak in the views of downtown Healdsburg, Fitch Mountain, and the surrounding Sonoma Hills. Portable heaters surround open-air dining tables, and there is a fire pit table. Servers are happy to wrap you in warm blankets as you sip a glass of wine and enjoy the sunset.

The Rooftop’s Bites menu was ideal for trying several items. A beach girl, I jumped on the chance to order local Marin Miyagi Oysters with Tomales Bay Mignonette. Rooftop Tacos, Banh Mi Sliders, and Truffle Fries completed our dinner order, and we ended our evening with Coconut Panna Cotta.

Catelli’s

A Geyserville restaurant, Catelli’s, is owned and operated by the third generation of this family. The chef, Domenica, is an area celebrity chef with a healthy food approach and the author of a cookbook, Mom-a-licious. We were thrilled to sample all her specialties.

Tiffany was our marvelous server, who ensured we had everything we could ask for and helped us make choices we were sure to love. Dining under the stars was a treat that we enjoyed on the checker-board patio.

I have never been able to pass up Burrata, so when I saw that one of the starters was Burrata & Prosciutto, I set my sights on that. The triple-cream mozzarella was served with prosciutto and grilled bread. My travel buddy homed in on the Kale Salad, loaded with oranges, pecans, parmesan cheese, and crushed croutons, drizzled with a local Dry Creek olive oil.

A margarita girl, I gathered all my bravery and ordered the Garden Jalapeno Margarita (they promised me it wasn’t too hot.) The drink was tequila infused with jalapeno, mixed with lime, agave, orange liqueur, and cilantro, in a chili salt-rimmed glass. Audrey was born in Tennessee, so the Tennessee Tart lit up her eyes: a mixture of bourbon, St. Germain, lemon juice, agave, and mint arrived to make her night. Then there were glasses of Marietta, an old vine red wine from Sonoma that was primarily Zinfandel and had a rich structure that paired perfectly with our entrees.

A glass of Silver Oak Cabernet stood up to our shared cheese, meat, and mushroom cream ravioli. We divided a plate of the chef’s famous 10-layer lasagna (including local ricotta, goat, and parmesan cheese.) The special of the day, Shishito Peppers with Aleppo and orange zest, drizzled with Nardello pepper aioli, rounded out our order.

It hardly seemed possible that there was room for dessert, but Tiffany described the Tiramitini as tiramisu in an espresso martini, and we were hooked. She was correct; it was delicious, but we were relieved we had only ordered one.

Where to Stay in Healdsburg

Dry Creek Inn is a convenient place to stay, providing easy access to the highway or the downtown area of Healdsburg. It has clean, quiet rooms, a beautiful pool, and a breakfast restaurant right out front. The renovated Tuscan-style Inn has an elevator and plenty of parking.

Next door is The Lodge at Healdsburg, an upscale hotel part of Hilton’s Tapestry Collection. The manager, Andrew, gave us the grand tour, so we know what we missed. The 60 king rooms are spacious, and each has a gas fireplace. They pour wine during happy hour in Alexander’s Café, also serving breakfast and bar bites.

Meeting and event rooms are available, as well as a covered patio. Outdoor spaces also have patio furnishings to make it easy to relax.

Harvest Fair

The regional Sonoma County Harvest Fair is the largest wine competition of its kind in the United States. Only local grapes from a Sonoma County AVA can be used in the wine to qualify for entry into the contest. Wine Road and the Harvest Fair worked together to allow us to explore even more local wines at the Harvest Fair. The Fair is held yearly in early October, and the date of October 11, 2025, has already been announced. The Sonoma County Fairgrounds’ Grace Pavilion in Santa Rosa, only fifteen miles from Healdsburg, hosts the event.

Select Sonoma County restaurants, caterers, and culinary newcomers serve their best wine-friendly bites at the one-night-only gala. It was the county’s wine event of the year, and everyone was in great spirits. *giggle*

The wineries that receive Gold, Double Gold, or Best of Class awards must pour their wines at the event so you truly taste the best of the best. Silver and Bronze winners or non-awarded wines may be poured, but it is not mandatory. It was exciting to meet so many winery owners, especially those we had visited and others on our itinerary for the coming week. Put next year’s Harvest Fair on your calendar; looking forward to something is always fun.

Plan Your Next Wine Country Trip

For more exciting trips, try some of my favorite wine-filled locations. Plan a trip to Corning and the Finger Lakes to visit as many wineries for tastings as possible, or take a road trip to North Carolina’s beautiful Yadkin Valley Wineries, or visit more towns in Sonoma County.