The North Bay's cheesemaking culture gets its own weekend: seminars and farm tours give way to a grand tasting and artisan marketplace in Petaluma, plus a cheese crawl through the makers at The Barlow in Sebastopol. Two decades in, and still the region's definitive curd-and-cracker pilgrimage.

Wine Road's most laid-back outing, timed to the start of barbecue season: twenty member wineries each pour the bottles they'd set beside whatever's on the grill — hot dogs and burgers, grilled salmon, chicken, summer vegetables — and weigh in on what to cook. One flat $50 ticket covers the whole day, with no per-winery fees and no reservations; you just show the pass on your phone at each stop. Capped at 200 tickets, so the pours and the conversation stay unhurried.

Sebastopol's love letter to the heirloom Gravenstein apple, spread across Ragle Ranch over the second weekend of August — orchard lore, craft and cider booths, live music, and farm-country food under the oaks. A West County tradition with deep roots.

Every other Wednesday, Sonoma County Vintners hands the wine wall at The Matheson over to a rotating cast of winemakers — a low-key, hour-long way to taste alongside the people who actually made the bottle, right in the heart of Healdsburg.

Sonoma County Vintners' roving tasting series — the expanded heir to Taste of Sonoma — touches down at a different standout winery each time, every stop pouring 20-plus producers around a theme or AVA and guided by sommelier Christopher Sawyer. Recent hosts include Bricoleur Vineyards; it's a curated, seasonal way to range across Sonoma without committing to a single appellation.

Wine Road's marquee fall weekend, and the fullest expression of its drink-this-with-that ethos: each of fifty-plus member wineries plates a bite of a favorite recipe and pours the wine built to match it, then posts the recipe online so you can rebuild the pairing at home. Past crowd-pleasers run from Sunce and Mazzocco to Notre Vue and Alexander Valley Vineyards, spread across Alexander, Dry Creek and the Russian River Valley over two unhurried days. For 2026 the weekend trails a one-night 50th-anniversary Grand Tasting on Friday, November 6 — Wine Road's half-century victory lap. The full participating roster posts in mid-August.

A harvest-season benefit for the Boys & Girls Clubs of Sonoma-Marin, set in downtown Healdsburg when the cellars are humming: sixty-plus producers pour limited-production Pinot Noir and sparkling at tasting booths, with a VIP passport buying an extra hour of face time and a charity auction sending 100% of proceeds to the clubs. The pouring bench leans serious — Williams Selyem, Merry Edwards and the sparkling house Iron Horse among them. Confirm the 2026 date before you plan around it.

One of California's oldest wine festivals — 129 years and counting — built around the historic Sonoma Plaza: a Blessing of the Grapes, a grape stomp, and a Grand Tasting in the old Sonoma Barracks that gathers fifty-plus valley producers under one roof. It's small-town pageantry that predates the whole modern wine-country idea, anchored by Sonoma Valley stalwarts like Anaba and Kenwood Vineyards, with a harvest dinner out at Viansa. Proceeds support the valley's vintners-and-growers foundation.

The West Sonoma Coast Vintners' annual showcase gathers the 'true coast' cult — forty-odd small producers farming the fog belt from Annapolis to the Sebastopol Hills — into one Sebastopol room to pour the Pinot, Chardonnay and Syrah you'll otherwise only pry loose from a mailing list. A VIP library hour opens the evening ahead of the grand tasting, with coast staples like Hog Island oysters to slow you down. Expect the likes of Littorai, Peay, Hirsch, Flowers and Occidental — the Who's Who of cool-climate Sonoma, in the one place they all turn up at once.

Three days of wine country at its most joyful: dinners and tastings around Healdsburg and the Russian River Valley, anchored by the signature Twilight T-Dance at La Crema's estate — a celebration that doubles as a benefit for Face to Face, Sonoma County's HIV/AIDS services.

A trade-and-press deep dive into Russian River Valley Pinot Noir — seminars, tastings, and grower dinners built for the industry rather than the public. Listed here for the record; admission is by application.

The Press Democrat's one-day grand tasting at Santa Rosa's Luther Burbank Center, built on a clever conceit: nearly a hundred gold-medal winners from the North Coast Wine Challenge poured alongside dishes from twenty-odd Wine Country chefs, with live music to keep it moving. It's an easy, all-under-one-roof sampler of the wider region — and a benefit for Sonoma Family Meal, the chef-and-farmer network that feeds neighbors through hard times.

Now in its fifth year, this four-day, town-wide affair pours global bottles alongside Sonoma's own and turns Healdsburg into one long tasting: a Welcome Celebration at Appellation Healdsburg, the Saturday Vintners Plaza Grand Tasting with 150-plus producers and a roster of national chefs, plus a Big Bottle Party at The Matheson and a sommelier-showdown dinner at Dry Creek Kitchen. Estate events fan out to Chalk Hill, Kendall-Jackson and Stonestreet, with a closing pizza-and-Pinot blowout in the Russian River Valley. Big-name chefs, deep cellars, and Healdsburg at its most polished.

The county vintners' annual barrel auction, where trade buyers bid on one-of-a-kind futures lots — an industry-and-media event rather than a public one. Listed for the record; attendance is invitation-only.

The Alexander Valley Winegrowers tore up the old ticketed-weekend model for 2026: all April, the valley's wineries simply open their doors for complimentary, no-appointment tastings (plus 10% off if you take a bottle home) — a 'Back to Our Roots' reset that drops the biggest barrier to wandering one of Sonoma's warmest, most Cabernet-friendly valleys. Show up at Alexander Valley Vineyards, J. Rickards or ACTA and taste for free; serious students can book the Wine 101 session or the all-women winemaker class at Silver Oak. The month's marquee sit-down is a four-family wine-paired dinner at The Matheson on April 18.

Dry Creek Valley's beloved spring passport, and in 2026 its 35th: one wristband, a long weekend, and fifty-plus family wineries each pairing their pours with a local-chef bite, live music, and the kind of unhurried hospitality the valley is built on. Zinfandel and old-vine Cabernet anchor the lineup — think Dry Creek Vineyard, Pedroncelli, Quivira and the bubbles of Breathless — with a Friday Twilight Welcome Party and a Saturday Toast & Taste anchored at Bacchus Landing. Proceeds feed the Dry Creek Valley Scholarship, and if you can't make the weekend, the new 'Twice as Nice' two-for-one tastings stretch from early April into June. Book early; it sells out.

Chef Charlie Palmer's cult two-day blowout hits its 19th year in 2026 with a new home — Appellation Healdsburg, his just-opened flagship resort — after two decades anchored at Hotel Healdsburg and Dry Creek Kitchen. The format holds: Friday's Taste of Pigs & Pinot turns sixty hand-picked Pinots loose in the blind-judged Pinot Cup, with pork in every conceivable form from Palmer and a bench of Sonoma kitchens including SingleThread, The Matheson and Diavola. This year's twists: an all-father-and-son chef lineup and the event's first all-female Gala winemaker roster, with Sonoma names like Blue Farm and Merry Edwards pouring. Proceeds fund the Palmer Family Education Foundation; tickets are gold dust.

Wine Road's spring rite: tasting wines still aging in the barrel, straight from the cellar, and reserving futures before they're ever bottled. A behind-the-scenes weekend across Alexander, Dry Creek, and the Russian River Valley that's pulled people up Highway 101 for decades.

A late-winter, countywide showcase now in its 17th year: from Petaluma to Cloverdale, more than a hundred restaurants put on three-course prix-fixe menus in the $30–60 range, making it the easiest week of the year to finally book the place you've been meaning to try. The 2026 edition leans hard into a 'Sonoma County Grown' theme spotlighting kitchens that source inside county lines — among them Stockhome, John Ash & Co. and Iron & Vine. No tickets, no passes; just reserve and go.

A month-long winter passport to the Sonoma Valley: from mid-February to mid-March, more than fifty wineries, tasting rooms and even restaurants pour a flat fifteen-dollar taste — no crowds, no fuss, the valley at its rain-green, off-season best. Just tell your host you're there for Sonoma Sips. The program now spills into the dining room too, with valley winemakers pouring alongside kitchens like Swiss Hotel and Sonoma Grille, and a capstone Winemaker's Pour in mid-March.

Wine Road opens the year with two days of library pours, futures, and winemaker face time across fifty-plus wineries — the off-season tasting weekend for people who'd rather have the tasting rooms (almost) to themselves.

Guerneville's summer-afternoon market is a proper river-town affair — a handful of local growers and makers setting up beside the Russian River Community Pantry, equal parts grocery run and neighborly catch-up before the evening fog rolls in.

An after-work market in the shade of Forestville's downtown park: late-afternoon produce, prepared food, and music timed so you can shop straight into dinner on a warm Russian River evening.

The far north end of the county throws the most unpretentious party around — a Friday street fair that gives way to a real headliner act on the Plaza, blues to bayou Americana, with a glass of Alexander Valley red in hand and not a velvet rope in sight.

On the Cloverdale Plaza at the county's northern edge, this market keeps things small and unhurried — seasonal produce, local honey and bread, and vendors who'll know your name by the second visit.

Leafy Walnut Park hosts Petaluma's afternoon market through the warm months — Sonoma-Marin produce, cheeses, and cut flowers a short stroll from the historic downtown.

Petaluma's east-side market runs year-round at Lucchesi Park — a dependable source for local produce, eggs, and bread whatever the season.

On summer Wednesdays, The Barlow's open-air market district throws a free concert among the tasting rooms, breweries, and food makers — Sebastopol's after-work answer to a beer garden with a band.

Every Wednesday evening through summer, Ives Park fills for Peacetown — a free community concert that's been a Sebastopol institution for years, with food, a beer garden, and a different band each week under the redwoods.

One of the West County's anchors: a year-round market on Sebastopol's downtown plaza, long on organic growers, artisan food, and the easygoing counterculture that flavors the whole town.

Through the summer, Old Courthouse Square becomes Santa Rosa's open-air pantry — rows of Sonoma County growers and food makers in the heart of the revived downtown.

A year-round neighborhood market at Farmers Lane Plaza, running midweek and weekends alike — straightforward, local, and reliable in every season.

The county's long-running 'Original' market gathers Sonoma growers at the Luther Burbank Center — a weekend institution, with a midweek edition through the growing season.

Summer Wednesdays, downtown Santa Rosa closes the streets around Old Courthouse Square for a full-on night market — food, live music, makers, and a few thousand neighbors making an evening of it.

Summer evenings on the Windsor Town Green, a market and a free concert run together into one long party — bring a blanket, graze the food trucks, and stay for the band.

Sunday mornings, the Windsor Town Green fills with Sonoma County growers and makers — a relaxed, family-paced market at the center of town.

Summer Sundays, Healdsburg's plaza hosts an easy afternoon of live music under the trees — pick up a wine-country picnic from the shops around the square and stake out a patch of grass.

Healdsburg's beloved summer concert series turns the plaza into a Tuesday-evening dance floor — a different band each week, families on blankets, and the whole town out as the light goes long.

Healdsburg's farmers' market is a serious one — a deep bench of Dry Creek and Alexander Valley growers, ranchers, and bakers, with a Saturday flagship and a midweek edition through the season.

Wednesday evenings, the Sonoma Botanical Garden stays open past closing for music in the amphitheatre, a glass poured by a rotating local vintner, and the long golden light over the valley. Bring a picnic; the dog's welcome too.

A small valley market under the oaks at the edge of Glen Ellen — neighborly, seasonal, and very much in the unhurried spirit of the Sonoma Valley back roads.

The Springs' own market brings fresh produce and a lively food scene to Boyes Hot Springs — a warm, working-neighborhood market that reflects the area's strong Latino community, just up the highway from the Sonoma Plaza.

Sonoma's year-round market at Arnold Field is a Friday-morning fixture — valley growers, ranchers, and bakers a few blocks off the historic Plaza, rain or shine.

The Plaza's warm-weather heartbeat: produce stalls and flower buckets ring the square while a live band plays the gazebo and locals spread blankets with a bottle of something local. The closest thing Sonoma has to a standing town reunion.