Healdsburg, California • Sonoma Wine Country
Things to Do in May 2026
in Healdsburg, CA
Farmers markets, wine festivals, live music, parades, and community events all month long.
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May is one of the most magical months in Healdsburg. The vines are leafing out, the plaza fills with the aroma of fresh produce, and the calendar bursts with festivals, outdoor concerts, and community traditions. From the nationally recognized Healdsburg Wine & Food Experience to the beloved Future Farmers Twilight Parade, there is no shortage of reasons to visit or explore your own backyard.
Below is every confirmed May 2026 event we’ve gathered from the City of Healdsburg, local wineries, event organizers, and community groups — listed in chronological order so you can plan your month with ease.
May 2026 Events
Healdsburg Jazz Annual Gala
The Healdsburg Jazz Festival kicks off the season with its annual fundraising gala at the Foley Family Community Pavilion. An elegant evening celebrating one of Northern California’s most acclaimed jazz organizations — featuring live music, fine wine, and community support for jazz education programs.
healdsburgjazz.org →Saturday Healdsburg Certified Farmers’ Market
Running every Saturday from April through December, this beloved weekly market features fresh-picked produce, flowers, cheese, honey, wild fish, artisan bread, handmade crafts, and live music. One of the original 22 certified farmers’ markets in California, founded in 1978. Runs 8:30 am to noon at the Foley Family Community Pavilion.
healdsburgfarmersmarket.org →SMART Healdsburg Extension Ribbon Cutting Celebration
The Sonoma-Marin Area Rail Transit (SMART) celebrates a major milestone in its extension of the regional rail line northward to Healdsburg. The $269M project — which will add roughly nine miles of new track from Windsor — marks a historic reconnection of Healdsburg to regional rail for the first time since 1958. Celebrate this community achievement at the Foley Family Community Pavilion.
sonomamarintrain.org →Run for Funds — Healdsburg Junior High
Lace up your sneakers and support Healdsburg Junior High students in this community fun run and fundraiser along downtown Healdsburg sidewalks. A great opportunity to cheer on local youth and contribute to school programs while enjoying the town’s beautiful streets.
City of Healdsburg Calendar →Tuesday Healdsburg Certified Farmers’ Market Opens
The beloved Tuesday market at the Foley Family Community Pavilion returns for the season starting May 12. Shop for seasonal fruits and vegetables, flowers, cheeses, honey, olive oil, wild fish, and handmade crafts every Tuesday through September 29. A perfect mid-week outing in the heart of wine country.
healdsburgfarmersmarket.org →Healdsburg Wine & Food Experience 2026
The premier food and wine celebration of Sonoma County returns for its 5th year, showcasing the region’s farmers, growers, winemakers, and chefs alongside globally recognized wines. Four days of tastings, seminars, chef dinners, and special events across Healdsburg. Highlights include the Grand Tasting on Saturday with 150+ wines and bites by nationally acclaimed chefs, a VIP Platinum Dinner at MacMurray Estate, and the Sunday Wine-Down Pool Party at Appellation Healdsburg.
healdsburgwineandfood.com →Outdoor Concert at Rodney Strong Vineyards: Grace Bowers
Wine country’s must-see concert of 2026. Breakout guitar sensation Grace Bowers — the 19-year-old award-winning guitarist who performed at the Grammys alongside Coldplay — headlines the iconic Rodney Strong Concert Green. Opening is country singer-songwriter Hannah Ellis, whose song “Wine Country” is a perfect match for the setting. Doors open 5:30 PM. A portion of proceeds supports Farm to Pantry. Part of the Healdsburg Wine & Food Experience.
rodneystrong.com/events →Healdsburg Wine & Food Experience: Grand Tasting
The centerpiece of the Healdsburg Wine & Food Experience. Over 150 wines, beers, and spirits from local and world-renowned artisans, paired with exceptional bites from acclaimed chefs including Food Network stars. VIP early entry begins at 11:00 AM; general admission at noon. Held at West Plaza Parking Lot and West Plaza Park in the heart of Healdsburg.
healdsburgwineandfood.com/events →Healdsburg Future Farmers Country Fair
One of Healdsburg’s oldest and most beloved community traditions. The fair runs Thursday through Sunday at Recreation Park, featuring a circus, carnival games, food, agricultural exhibits, livestock, and FFA and 4-H youth showcasing their animals and projects all year in the making. The livestock auction takes place Saturday at 2:00 PM. Bring the whole family for this cherished annual celebration of the agricultural spirit that defines Healdsburg.
healdsburgfair.org →Twilight Parade — Healdsburg Future Farmers Country Fair
The Thursday before Memorial Day means one thing in Healdsburg: the Twilight Parade. This beloved annual procession winds through downtown with colorful floats, spirited community groups, marching bands, and festive performers. The route begins near St. John the Baptist Catholic Church on East and Matheson St., continuing through Center St. and Piper St. before ending at Recreation Park — where the Country Fair officially kicks off immediately after.
City of Healdsburg →E-Waste & Mattress Collection
Bring your old electronics and mattresses to the Abel De Luna Community Center for responsible recycling and disposal. This free community event, organized by Conservation Corps North Bay, keeps hazardous materials out of landfills and provides an easy drop-off option for Healdsburg residents.
City of Healdsburg Calendar →Tuesdays in the Plaza — Summer Concert Series Opens
Healdsburg’s beloved free outdoor concert series returns to the Plaza, running every Tuesday evening from May 26 through August 25. Grab a blanket, bring a picnic, and enjoy live music under the open skies in the heart of Healdsburg. A signature summer tradition for families, couples, and locals alike — completely free to attend.
healdsburg.gov Special Events →Sundays in the Plaza — Summer Series Opens
A companion to Tuesdays in the Plaza, this Sunday evening concert series kicks off May 31 and runs through August 9. Spend a perfect Sonoma County Sunday evening on the Healdsburg Plaza with live music, family-friendly vibes, and the warm glow of wine country summer. Free to the public.
healdsburg.gov Special Events →Always in May
Healdsburg Tasting Rooms — Open Daily
May is prime tasting season in Healdsburg. Dozens of world-class tasting rooms line the Plaza and surrounding areas, including Rodney Strong Vineyards, Jordan Winery, J Vineyards, Aperture Cellars, Ferrari-Carano, Dry Creek Vineyard, Stonestreet, Kendall-Jackson, MacRostie, and many more. Most require reservations. The Healdsburg Chamber of Commerce maintains a current directory.
Healdsburg Chamber — Wineries →Healdsburg Parks, Trails & River Recreation
May is ideal for exploring Healdsburg’s outdoor assets before summer heat arrives. Paddle or float the Russian River from Healdsburg Veterans Memorial Beach, hike the trails at Riverfront Regional Park, or explore the SMART Pathway multi-use trail corridor. Lake Sonoma — just 11 miles away — offers fishing, boating, and camping with stunning views of oak-dotted hills.
Sonoma County Tourism — Healdsburg →
