Top 10 Healdsburg Outdoor Wine Tastings with Fabulous Food Pairings

Eating and drinking is always on the agenda in Healdsburg, a vine-carpeted corner of Sonoma County where three wine regions intersect with a charming town square filled with shops, restaurants and tasting rooms. Since the pandemic, several Healdsburg wineries have embraced alfresco entertaining to offer even more fabulous food pairings, served on Instagram-worthy patios. Here is our Top 10 list of the best Healdsburg outdoor wine tasting experiences with food.

This list focuses on the best Healdsburg wineries with outdoor wine tastings that include serious food pairings in Northern Sonoma County, organized by wine region: Alexander Valley, Dry Creek Valley and Russian River Valley. There are many local wineries with lovely settings for outdoor wine tasting, but if they don’t serve substantial food—i.e. more than a cheese plate and popcorn—they didn’t make the cut.

Virtually all wineries with food pairings require reservations, so visit the websites to book as far in advance as possible. Outdoor wine tastings with food are usually offered on select days, as chefs needs their weekends off too, even if those come mid-week.

Alexander Valley: Healdsburg Outdoor Wine Tastings

Savor French-Inspired Food & Wine on one of Jordan Winery’s Patios

The roots in culinary hospitality run deep at Jordan. For more than 40 years, the Jordans have been pairing their elegant wines with exquisite food pairings at the French-inspired chateau, and their commitment to outdoor entertaining grown even stronger in recent years. Jordan now offers three outdoor wine tasting experiences with food pairings on the winery’s patios. The new  Chef’s Terrace Tasting ($110), hosted Thursday-Monday from mid-June through mid-September on the chateau’s oak-shaded terrace, features a seated tasting menu by longtime Michelin-star winner Chef Jesse Mallgren, as well as freshly baked bread from the terrace’s wood-fired oven. Guests can also partake in the award-winning Estate Tour & Tasting ($160), a three-hour culinary excursion across the 1,200-acre ranch, which includes breakfast on the Bacchus courtyard patio, before a garden walk and vegetarian-driven food pairings served at a stone patio alongside Jordan’s large lake. The journey concludes with a seated food and wine pairing in an indoor-outdoor glass pavilion at Vista Point, Jordan’s highest hilltop, with tableside presentations by the chef. On Friday nights in August, Chef Mallgren is hosting Jordan’s first Parisian Pop-Up Dinner series ($350), a progressive experience with enchanting wine and food pairings that begins in the Bacchus Courtyard before moving to the chateau terraces. “The experiences are all very different, so it’s fun for me as a chef to utilize ingredients from different parts of the property in the menu,” Mallgren says. “The best part is having the direct interaction with our guests and seeing their reactions to each pairing.”

Get Your Michelin Fix with Boxed Lunch at Medlock Ames

If you haven’t been able to score a table at three Michelin star SingleThread for any number of reasons, Medlock Ames now offers an outdoor food and wine pairing that gets your taste buds one step closer to the holy grail of Healdsburg restaurants. The Wine Pairing Lunch with SingleThread ($175) features a bento box filled with tasty, garden-centric bites from the restaurant to pair with Medlock Ames’ small-batch, organically farmed wines from Bell Mountain Vineyard—served in the gardens at their century-old, restored tasting room that once housed the historic Alexander Valley general store.

Robert Young Scion Experience on the Winery Patio

Perched on a knoll with stunning vineyard views, Robert Young’s newish Scion House boasts a lovely back patio for outdoor wine tasting just 15 minutes from downtown Healdsburg. The Scion Experience ($70) lets guests explore estate, single-block reserve wines paired with local bites. Seating can be requested on the shade patio overlooking Alexander Valley or inside the modern-farmhouse tasting room. “We love to welcome guests and share our family’s 165-year history on our ranch in Alexander Valley,” says Robert Young, fifth-generation family member and tasting room manager.

Dry Creek Valley: Healdsburg Outdoor Wine Tastings

Gourmet Pizza & Coastal Wines on the Patio at Reeve

Tucked away on an oak-shrouded benchland, Reeve’s hacienda tasting room opens to a lovely stone patio filled with pots of succulents that overlooks a vineyard. Two wine tasting flights are offered (Wayfare $50 and Kismet $75), and both include a gourmet pizza from their wood-fired oven. Additional pizzas can be purchased for $25, and trust us—you’ll order at least one more. Reeve is known for making wines from coastal vineyards, so chardonnay and pinot noir dominate this outdoor wine tasting, but there’s still plenty of diversity in the wines.

Relax with Several Outdoor Wine & Food Tasting Options at Comstock

After growing grapes in Dry Creek for a decade, the Comstock family decided to build their dream winery and start making their own wines in 2012. A decade later, the modern barn-style tasting room, which was built for entertaining, boasts spacious covered patios that overlook the vineyards and bocce ball courts. Chef Jude Affronti cooks up three different Healdsburg outdoor wine tasting experiences with food pairing: Wine & Mezze Platter Flight ($30), Wine & Grilled Cheese Flight ($75) and the Wine & Wood Fired Pairings Flight ($125).

Hilltop Wine Tasting with Italian Food Pairings at Trattore Farms

Owner Tim Bucher grew up on a dairy farm in Healdsburg and purchased his first vineyard when he was just 16 years old. After making wine and olive oil commercially for several years, he and his wife, Mary, unveiled their Italian farmhouse-style tasting room on a gorgeous hilltop in western Dry Creek Valley in 2015. Home to both Trattore Farms wines and Dry Creek Olive Company oil and vinegars, the tasting room offers an array of tastings daily ($20-$30), and views from the patio are worth a trip, even if you aren’t hungry. Pizzas ($20) from their wood-fired oven are served on Sundays from April through October, while guests can order seasonal paninis and charcuterie boards ($20-$35) year-round. Food pairings are offered to guests upon arrival, but if you are traveling with a group larger than six, you’ll need to make an advance reservation. Two additional wine and food pairings will be available to book directly on the website in the future, according to the owners. “While amazing on their own, our Rhône-style wines and artisan olive oils truly shine when paired with food,” says Mary Louise Bucher, co-owner, master miller and club manager. “We do our best to provide selections of pairings that truly highlight our olive oils and vinegars, and pair well with our wines for a complete culinary experience.”

Sip and Snack with Fontana Pergola at Ferrari-Carano

Known for their Italian-inspired villa and crowd-pleasing wines, Ferrari-Carano has combined all the best Cs in life with its new Fontana Pergola ($95) experience: charcuterie, cheese, caviar, chardonnay and cabernet. Hosted in an area of the estate never before open to the public, the Fontana Pergola tasting features five reserve wines (a pinot noir is included in the mix) with the option of adding a platter of charcuterie and cheese, or caviar and chips, to your reservation. The setting is replete with a grand fountain (fontana in Italian) and century-old olive trees. Ferrari-Carano’s sister winery, Chalk Hill, offers similar snack add-ons at its  Vineyard Overlook Experience over in the Chalk Hill appellation.

Russian River Valley: Healdsburg Outdoor Wine Tastings

Seasonal Bites Pair with Estate Wines in the Flowers Garden

One of the most memorable tasting room transformations in Healdsburg, House of Flowers debuted in the summer of 2019. The prolific gardens created by the previous owners were reimagined and expanded to include several cabanas and enchanting enclaves for seated tastings. Three tastings are hosted in one of the garden’s sitting areas or inside the airy, modern tasting room, including the Estate Vineyard Immersion ($125), which features seasonal bites by the estate chef paired with single-vineyard wines.

Pizzas Served from an Airstream and Pinzgauer Lunch at Thomas George

Located on the west end of Westside Road (aka the “Miracle Mile of Pinot Noir”), Thomas George is a family-owned and operated winery known for small-lot wines and its hillside wine caves. In recent years, owner Tom Baker has expanded his en-plein-air hospitality to include an Airstream converted to a mobile commercial kitchen, where the estate chef prepares food pairings for all of the  Winery Experiences. Outdoor wine tastings served with food at this rural Healdsburg producer include the Single Vineyard Outdoor Reserve Tasting ($60), which features pizza, and the Wine Safari ($250), which includes a vintage Pinzgauer tour and a four-course lunch.

Bricoleur Vineyards

This newish Russian River Valley estate, located just south of Healdsburg in rural Windsor, was founded by the Hansons, relatives of the legendary winemaker Pietro Carlo Rossi. They’ve built the barn-style tasting room with culinary-focused wine tastings in mind, and guests can watch the culinary staff in action in the open kitchen. The property is filled with patios, and guests can choose their own spot to sip and nosh with the Essentials Picnic ($75), which includes a red wagon to pull provisions if you choose a remote dining location. The Soaring Flight ($75), which features three food and wine pairings, is typically served on the shade patio overlooking their pond, while the Rooted Tasting ($125) with six wine and food pairings takes place indoors. Rosé in the Roses ($130), a family-style lunch paired with a magnum of rosé, is served under a pergola next to their bocce court. Several dinner parties are also hosted on set days on the winery patio, showcasing Bricoleur wines and fresh ingredients sourced sustainably and locally, some of it from their own garden

Explore our comprehensive list of Sonoma wineries with food, which includes indoor wine and food pairing experiences, as well as wineries in other parts of Sonoma County farther away from Healdsburg.