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Featured Upcoming Events

All Upcoming Events

Healdsburg Farmers Market

April 15-December 23, 2023

Saturday’s April 15 – December 23, 2023 8:30 – Noon West Plaza Parking Lot (one block off the Plaza) Tuesday’s May 16 – September 26, 2023 9AM – 12:30PM On the Plaza Downtown Founded in 1978, the Healdsburg Certified Farmers’

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Summer Concert Series at Orsi Family Vineyards

September 23, 2023

Soak up the sunshine during an afternoon of wine, food, and music at Orsi Family Vineyards in Healdsburg for our much-loved Music in the Vineyards concert series – this month’s show features a spectacular performance by Fleetwood Mac tribute band,

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Fall Wine Trail

September 23, 2023

Get out and explore along the Wine Road, check out some new wineries, visit your long time favorites and stock up on some of your favorite wines for fall. Join over 30 wineries for a day of fall adventure. What

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Lancaster Estate Harvest Celebration

September 23, 2023

Join us to celebrate the 2023 harvest season, and unveiling of our new Guild Member House. Guests will enjoy a festive afternoon among the stunning fall vineyards of our 53-acre estate and wine cave, and delight in the tastes of

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Backyard Night at Medlock Ames

September 24, 2023

Join us for the final Backyard Night at Medlock Ames! Watch the sun go down while enjoying a relaxing evening of live music, wine, and food from Molti Amici at our Historic Healdsburg Tasting Room. Grab a bottle from our

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Happy Hour at Oakville Grocery/Wine Merchant

September 29, 2023

Join the team at Oakville Grocery & Wine Merchant for HAPPY HOUR! The iconic wine country institution serving the Healdsburg community for over 20 years. $6 Hen House IPA $6 Select wines by-the-glass $5 Slices of pizza

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Harvest Wellness Weekend at Montage Healdsburg

September 30-October 1, 2023

Harvest season is the culmination of a year’s worth of hard work in the vineyards, as well as our own dedication to personal development. Keeping wellness at the forefront, this is a time to come together and serve as a

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Vineyard to Spa at Montage Healdsburg

September 30-November 30, 2023

Experience an exclusive spa treatment at Montage Healdsburg highlighting grape skins and seeds harvested directly from our own resort vines. Blended with the finest mineral salts and essential oils infused with grapefruit and black pepper, the elements are full of

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Free Family Music Matinee with Healdsburg Jazz

September 30, 2023

Enjoy a FREE family matinee concert hosted by Healdsburg Jazz and tailored for young kids, teenagers, and families. Special guest artist Terrence Brewer and his quartet will perform a one-hour concert featuring original music, standards, and music by composer Vince Guaraldi, who composed the

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Prune Box Derby

October 1, 2023

Returning for the first time since 1937, Healdsburg Prune Box Derby is COMING BACK!!! An ancient Healdsburg tradition is being brought back to life this fall after 86 years! The Healdsburg Prune Box Derby is a FREE event, where community

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Summer Concert Series at Orsi Family Vineyards

October 7, 2023

Soak up the sunshine during an afternoon of wine, food, and music at Orsi Family Vineyards in Healdsburg for our much-loved Music in the Vineyards concert series – this month’s show features a spectacular performance by Journey tribute band, Journey

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Healdsburg African American History Walk

October 7, 2023

Join us for our Healdsburg African American History Walk on Saturday October 7, 2023 from 10-11:30am. Meet at the Healdsburg Museum (221 Matheson Street, Healdsburg). $20 per person. $10 for Museum members. Tickets are limited. RSVP to Holly at holly@healdsburgmuseum.org.

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4th Annual Harvest Party

October 8, 2023

Come join us for our 4th Annual Harvest Party! Enjoy wine, music, bocce ball, and all-around fun at Bricoleur Vineyards. Bottles of Wine will be available for purchase! Also, our Club Members will be able to pick up their Fall

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Winemaker Harvest Walk and Tasting at West Wines

October 8, 2023

Walk the beautiful upper vineyards at West Wines with views of the Dry Creek Valley just before harvest with winemaker Katarina Bonde. During this unique experience in a small group, we will pick cabernet sauvignon grape samples and field test

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Sonoma County Harvest Fair

October 14, 2023

The Harvest Fair Grand Tasting Event features the area’s best wine and food, along with beers and ciders, all produced in Sonoma County!  With over 100 wineries participating, even the most experienced connoisseur is sure to find a new favorite

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Healdsburg Crush: Pouring at the Plaza

October 15, 2023

Join us for the ONLY wine tasting event that takes place on the Healdsburg Plaza! Along with approximately 65 premium wineries, we invite you to come spend the day enjoying some of the best Pinot Noir, Chardonnay and Sparkling Wines

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Comstock Wines Fall Winemaker Dinner

October 21, 2023

Comstock Wines Fall Winemaker Diner will roll out the red carpet for an unforgettable dining experience set in our Cabernet Vineyard. Join General Manager, Kelly Comstock and Winemaker, Chris Russi for a delicious four-course perfectly paired wine dinner from our

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Harvest of Hope 2023

October 22, 2023

Reach for Home works toward this goal every day with programs promoting self-sufficiency, independence and permanent housing. Harvest of Hope celebrates and supports this mission. As an attendee, you’ll enjoy stories of hope like this, delicious hors d’oeuvres, amazing wine and

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Locals Thursdays & Karaoke at Coyota Sonoma

October 26, 2023

JOIN US FOR ANOTHER LOCALS NIGHT at Coyote Sonoma! ENJOY SELECT $5 BEERS AND WINE. TAPROOM OPENS AT 4 PM. NO RESERVATIONS NEEDED – JUST COME ON IN! Karaoke begins at 7 PM on the indoor stage. Take center stage

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Día de los Muertos at Healdsburg Plaza

October 29, 2023

Live Music Día de Muertos features live music from various artists throughout the day at this annual celebration. Dance Performances Enjoy the traditional dance performances from Aztec dancers, folkloric dancers, and more throughout the day. Food Vendors Come hungry! Local

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Wine & Food Affair 2023

November 4-5, 2023

Join Wineroad for a weekend of wine and food pairing in the Alexander, Dry Creek and Russian River Valleys. FRIDAY a few wineries will be hosting Happy Hours or evening tasting, which will not be part of the weekend ticket.

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Rodney Strong Winery’s Fall Makers Market

November 18, 2023

No Admission Fee Join us for our third annual fall market on our expansive Concert Green! Support 20+ local artisans and start your holiday shopping while enjoying a glass of wine.  Treat yourself to some delicious bites available for purchase

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Fall Maker’s Market at Rodney Strong Vineyards

November 18, 2023

Join at Rodney Strong Winery for our third annual fall market on our expansive Concert Green! Support 20+ local artisans and start your holiday shopping while enjoying a glass of wine.  Treat yourself to some delicious bites available for purchase

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2023 Healdsburg Turkey Trot – Thanksgiving Day!

November 23, 2023

The annual 5K fun run/walk through the streets of Healdsburg promises a great time with our community – enjoy the morning in beautiful downtown Healdsburg as you work up an appetite for Thanksgiving Dinner!  The Rotary Club of Healdsburg Sunrise

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Tree Lighting at Montage Healdsburg

November 30, 2023

Experience the magic of the season at Montage Healdsburg‘s tree lighting. Join us for festive cheers and sparkling moments. Please meet in the lobby for this festive experience. Call (707) 209-1390 for Information

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Merry Healdsburg – Tree Lighting Celebration

December 1, 2023

Celebrate the holidays on the Plaza with the annual Merry Healdsburg Tree Lighting! Bring the whole family to enjoy a winter wonderland downtown with carriage rides, live holiday music, and much more! Tree Lighting Celebration The Tree Lighting Ceremony begins

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Winter Solstice at Montage Healdsburg

December 21, 2023

As the year draws to a close and the vines return to hibernation, spend the first day of winter in a restorative yoga experience at Montage Healdsburg. Participation is open to guests 16 and older. Please note reservations are required

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Christmas Eve Brunch at Montage Healdsburg

December 24, 2023

Cheers to the most wonderful time of the year at Montage Healdsburg. Toast under our Montage Mistletoe before celebrating in Hazel Hill with a Christmas Eve grand brunch buffet. $165 per adult | $65 per child Call (707) 354-6900 for

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Christmas Eve Dinner at Montage Healdsburg

December 24, 2023

Gather with loved ones, making seasonal spirits brighter in Hazel Hill. Montage Healdsburg invites you to a magical night at our annual Christmas Eve dinner featuring merry fixings of gourmet á la carte selections. Call (707) 354-6900 for Hazel Hill

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Christmas Day Feast at Montage Healdsburg

December 25, 2023

Make your day merry and bright with Montage Healdsburg’s annual Christmas Day celebration featuring an indulgent three-course prix fixe menu atTreat yourself to Beef Wellington, Suckling Pig, Maine Lobster and other delectable options. $175 per adult | $80 per child

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31st Annual Winter WINEland 2024

January 13-14, 2024

After the busy holiday season, now is the time to Restock your wine collection, join some wine clubs, and take the opportunity to taste wines you may have never even heard of before. Make it a weekend of discovery. Make

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Barrel Tasting 2024

March 2-3, 2024

The magic of Barrel Tasting is to get into the cellar and taste wines directly from the barrels.  Almost all of the wineries will be selling futures – so plan now to taste…then buy the future! Many of the wines

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