Wine Country Life Vacation Homes

ART NITE ~ STAY HEALDSBURG
2026-05-07 17:00 - 19:00 (America/New_York)
Art Nite

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Name: Art Nite

Date: May 7, 2026
Time: 5:00 PM – 7:00 PM PDT

Website: https://www.artnitehealdsburg.com/

Event Description:

Discover the Art. Savor the Flavor. Find Something Special.
ARTNITE Healdsburg is a new community event celebrating art and creativity with over 20 galleries participating.
DISCOVER THE ART
Visit our downtown galleries and collect your stamp.
SAVOR THE FLAVOR
Show your “artnite” passport at participating restaurants and wineries for a free treat, pour or special perk.
FIND SOMETHING SPECIAL
Shop the boutiques and retail stores along the way! Surprises await – shops may offer treats, delights, or a bit of magic!
WWW.ARTNITEHEALDSBURG.COM
Find the gallery map and a list of participating restaurants and wineries online. Pick up your ARTNITE passport available at any downtown gallery, and start your journey anywhere!
#artnitehealdsburg
From 5pm – 7pm every 1st Thursday of the month
Thank you to @stayhealsburg and @healdsburgchamber for sponsoring our event through their District Development Program. With the support of the hotel partners in Healdsburg, these annual sponsorships fund events that enhance the visitor experience when enjoying our wonderful town. To book your stay for this event, visit www.stayhealdsburg.com.

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Date/Time Information:

From 5pm – 7pm every 1st Thursday of the month

Fees/Admission:

Free event

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ART NITE ~ STAY HEALDSBURG
2026-05-07 17:00 - 19:00
Art Nite

Share:

Name: Art Nite

Date: May 7, 2026
Time: 5:00 PM – 7:00 PM PDT

Website: https://www.artnitehealdsburg.com/

Event Description:

Discover the Art. Savor the Flavor. Find Something Special.
ARTNITE Healdsburg is a new community event celebrating art and creativity with over 20 galleries participating.
DISCOVER THE ART
Visit our downtown galleries and collect your stamp.
SAVOR THE FLAVOR
Show your “artnite” passport at participating restaurants and wineries for a free treat, pour or special perk.
FIND SOMETHING SPECIAL
Shop the boutiques and retail stores along the way! Surprises await – shops may offer treats, delights, or a bit of magic!
WWW.ARTNITEHEALDSBURG.COM
Find the gallery map and a list of participating restaurants and wineries online. Pick up your ARTNITE passport available at any downtown gallery, and start your journey anywhere!
#artnitehealdsburg
From 5pm – 7pm every 1st Thursday of the month
Thank you to @stayhealsburg and @healdsburgchamber for sponsoring our event through their District Development Program. With the support of the hotel partners in Healdsburg, these annual sponsorships fund events that enhance the visitor experience when enjoying our wonderful town. To book your stay for this event, visit www.stayhealdsburg.com.

To Current Calendar

Date/Time Information:

From 5pm – 7pm every 1st Thursday of the month

Fees/Admission:

Free event

ART NITE ~ STAY HEALDSBURG
2026-05-07 17:00 - 19:00
Art Nite

Share:

Name: Art Nite

Date: May 7, 2026
Time: 5:00 PM – 7:00 PM PDT

Website: https://www.artnitehealdsburg.com/

Event Description:

Discover the Art. Savor the Flavor. Find Something Special.
ARTNITE Healdsburg is a new community event celebrating art and creativity with over 20 galleries participating.
DISCOVER THE ART
Visit our downtown galleries and collect your stamp.
SAVOR THE FLAVOR
Show your “artnite” passport at participating restaurants and wineries for a free treat, pour or special perk.
FIND SOMETHING SPECIAL
Shop the boutiques and retail stores along the way! Surprises await – shops may offer treats, delights, or a bit of magic!
WWW.ARTNITEHEALDSBURG.COM
Find the gallery map and a list of participating restaurants and wineries online. Pick up your ARTNITE passport available at any downtown gallery, and start your journey anywhere!
#artnitehealdsburg
From 5pm – 7pm every 1st Thursday of the month
Thank you to @stayhealsburg and @healdsburgchamber for sponsoring our event through their District Development Program. With the support of the hotel partners in Healdsburg, these annual sponsorships fund events that enhance the visitor experience when enjoying our wonderful town. To book your stay for this event, visit www.stayhealdsburg.com.

To Current Calendar

Date/Time Information:

From 5pm – 7pm every 1st Thursday of the month

Fees/Admission:

Free event

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CREATIVE CANVAS: GUIDED PAINTING - THURSDAY EVENINGS ~ STAY HEALDSBURG
2026-05-07 18:00 - 20:00
Creative Canvas: Guided Painting – Thursday Evenings

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Name: Creative Canvas: Guided Painting – Thursday Evenings

Date: May 7, 2026
Time: 6:00 PM – 8:00 PM PDT

Website: http://www.heartizens.org

Event Description:

Get ready for a fun and creative evening at Creative Canvas with Mona! In this adults-only, step-by-step painting class, Mona will guide you through creating a beautiful masterpiece—no experience required! Whether you’re a seasoned artist or picking up a brush for the first time, this class is designed to be fun, easygoing, and inspiring.
Feel free to bring your favorite beverage, whether it’s wine, soda, or tea, and enjoy the evening with friends as you paint, sip, and relax. It’s a perfect way to unwind and unleash your inner artist!

CREATIVE CANVAS: GUIDED PAINTING - THURSDAY AFTERNOONS ~ STAY HEALDSBURG
2026-05-07 18:00 - 20:00
Creative Canvas: Guided Painting – Thursday Evenings

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Name: Creative Canvas: Guided Painting – Thursday Evenings

Date: May 7, 2026
Time: 6:00 PM – 8:00 PM PDT

Website: http://www.heartizens.org

Event Description:

Get ready for a fun and creative evening at Creative Canvas with Mona! In this adults-only, step-by-step painting class, Mona will guide you through creating a beautiful masterpiece—no experience required! Whether you’re a seasoned artist or picking up a brush for the first time, this class is designed to be fun, easygoing, and inspiring.
Feel free to bring your favorite beverage, whether it’s wine, soda, or tea, and enjoy the evening with friends as you paint, sip, and relax. It’s a perfect way to unwind and unleash your inner artist!

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Location:

Heartizens
444 Moore Lane
Healdsburg, Ca 95448

Date/Time Information:

Thursdays Starting November 21st
6pm – 8pm

Contact Information:

Jen Utsch
Send an Email

Fees/Admission:

$15 Pre-Register or $20 Drop-In

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CREATIVE CANVAS: GUIDED PAINTING - THURSDAY EVENINGS ~ STAY HEALDSBURG
2026-05-07 18:00 - 20:00

L0NGB0ARD VINEYARDS WINE, DINE & DANCE WITH JUNK IN THE TRUNK & AD0B0S N' M0RE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00
Longboard Vineyards Wine, Dine & Dance with Junk in the Trunk & Adobos N’ More

May 8, 2026

5:00 pm

– 7:00 pm

Longboard Vineyards

May08

Friday Night Music, Wine & Dine at Longboard Vineyards
Featuring Junk in the Trunk & Adobos n’ More
Join us for a fun, high-energy Friday night at Longboard Vineyards in our Barrel Room, located in downtown Healdsburg, featuring live music, award-winning wine, and bold, comforting cuisine. Our Music, Wine & Dine Night pairs the lively sounds of Junk in the Trunk with delicious Filipino dishes from Adobos n’ More.
Junk in the Trunk brings an upbeat mix of familiar favorites and danceable tunes, creating the perfect soundtrack for a relaxed and social evening surrounded by barrels and warm winery ambiance. Enjoy Longboard’s wines by the glass or bottle while Adobos n’ More serves classic Filipino comfort food, lumpia, chicken and pork bowls, Soups, known for rich, savory flavors and home-style cooking.
Friday | 5:00 PM – 7:00 PMFree entry
Please note:This is an over-21 event inside the Barrel Room.Under-21 guests and leashed pets are welcome on the patio only.
Come grab a seat early and enjoy a classic Sonoma County night of great music, great wine, and great food.
Wine available for purchaseLive music by Junk in the TrunkFood by Adobos n’ More (Filipino cuisine)Location: Longboard Vineyards Barrel RoomAddress: 5 Fitch Street, Healdsburg, CA 95448

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LONGBOARD VINEYARDS WINE, DAINCE & DANCE WITH JUNK IN THE TRUNK & AD0B0'S N' M0RE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

LONGBOARD VINEYARDSWINE, DINE & DANCE WITH THE JUNK IN THE TRUNK & AD0BOS N' M0RE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

LONGBOARD VINEYARDS, WINE DINE & DANCE WITH JUNK IN THE TRUNK & AD0B0S N' M0RE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

LONGBOARD VINEYARDS WINE, DINE & DANCE WITH JUNK IN THE TRUNK & AD0B0S N' M0RE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

LONGBOARD WINE, DINE & DANCE WITH THE JUNK IN THE TRUNK & AD0B0S N' M0RE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

LONGBOARD VINEYARDS WINE, DINE & DANCE WITH THE JUNK IN THE TRUNK & ADOBOS N' MORE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

LONGBOARD VINEYARDS WINE, DINE & DANCE WITH JUNK IN THE TRUNK & ADOBOS N' MORE ~ STAY HEALDSBURG
2026-05-08 17:00 - 19:00

DAVID SEDARIS ~ STAY HEALDSBURG
2026-05-08 20:00 - 22:00
David Sedaris

Friday, May 8, 2026

8:00 pm

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🔑 Featuring a pre‑show Club for membership levels $500+. Click here for info.

David Sedaris is one of America’s pre-eminent humor writers. He is a master of satire and one of today’s most observant writers.
Beloved for his personal essays and short stories, David Sedaris is the author of the New York Times bestsellers Barrel Fever, Holidays on Ice, Naked, Me Talk Pretty One Day, Dress Your Family in Corduroy and Denim, When You Are Engulfed in Flames, Let’s Explore Diabetes with Owls, and Calypso. His book, The Best of Me, collects 42 previously published stories and essays. Sedaris also wrote Squirrel Seeks Chipmunk: A Modest Bestiary, a collection of fables with illustrations by Ian Falconer. He is the editor of Children Playing Before a Statue of Hercules: An Anthology of Outstanding Stories. His pieces regularly appear in The New Yorker and have twice been included in “The Best American Essays.”

THIRD PARTY RESELLERS
Don’t get taken by deceptive online resellers who use bots to buy tickets and then mark up their prices. The only safe way to protect your purchase and guarantee the best seats at the lowest cost is to work directly with us: through our website, by phone, or at our box office in Santa Rosa. Plus, we’re not bots. Our friendly team members are easily accessible by phone or at the box office to provide customer support.

MOM & ME FLORAL TEA ~ STAY HEALDSBURG
2026-05-09 11:30 - 13:30
May 9, 2026

Mom & Me Floral Tea

Visit Website

info@bohomanor.com

Delicate, whimsical, and full of heart, Mom & Me Floral Tea is a charming celebration of motherhood and togetherness. Designed for mothers and children, this daytime event transforms Boho Manor into a storybook tea garden filled with florals, pastel décor, and vintage-inspired details.
Guests enjoy a traditional tea service with delicate pastries, finger sandwiches, and sweet treats, all beautifully presented. Little ones delight in the magic of the setting while moms savor a moment of connection and calm. A picture-perfect experience that becomes a treasured memory.

Event Time

11:30 am – 1:30 pm

Boho Manor
20822 River Blvd.
Monte Rio, CA 95462
Get Directions

B0BBY RUSH & N0RTH MISSISSIPPI ALLSTARS ~ STAY HEALDSBURG
2026-05-09 20:00 - 22:00
Bobby Rush & North Mississippi Allstars

Saturday, May 9, 2026

8:00 pm

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Modern Mississippi Hill Country band North Mississippi Allstars and blues legend Bobby Rush are co-headlining this unique event, with each artist performing separately before joining together to honor their Mississippi blues roots.
North Mississippi Allstars was started by brothers Luther and Cody Dickinson in 1996 as a loose collective of musicians from their North Mississippi home. They were inspired by their father Jim Dickinson as well as neighbors and musical elders of their community, including RL Burnside, Junior Kimbrough, Otha Turner, and Fred McDowell. They have multiple Grammy® nominations for their acclaimed experimental albums, and the latest album, Still Shakin’, is out now.
The 91-year-old Bobby Rush is a three-time Grammy Award® winner for “Best Traditional Blues Album” for Porcupine Meat, Rawer than Raw, and 2024’s All My Love for You. He is also a 16-time Blues Music Awards winner (with 56 career nominations) and has been inducted into the Blues Hall of Fame, Mississippi Musicians Hall of Fame and Rhythm & Blues Hall of Fame.

THIRD PARTY RESELLERS
Don’t get taken by deceptive online resellers who use bots to buy tickets and then mark up their prices. The only safe way to protect your purchase and guarantee the best seats at the lowest cost is to work directly with us: through our website, by phone, or at our box office in Santa Rosa. Plus, we’re not bots. Our friendly team members are easily accessible by phone or at the box office to provide customer support.

BOBBY RUSH & NORTH MISSISSIPPI ALLSTARS ~ STAY HEALDSBURG
2026-05-09 20:00 - 22:00
Bobby Rush & North Mississippi Allstars

Saturday, May 9, 2026

8:00 pm

BUY TICKETS

🔑 Featuring a pre‑show Club for membership levels $500+. Click here for info.

Modern Mississippi Hill Country band North Mississippi Allstars and blues legend Bobby Rush are co-headlining this unique event, with each artist performing separately before joining together to honor their Mississippi blues roots.
North Mississippi Allstars was started by brothers Luther and Cody Dickinson in 1996 as a loose collective of musicians from their North Mississippi home. They were inspired by their father Jim Dickinson as well as neighbors and musical elders of their community, including RL Burnside, Junior Kimbrough, Otha Turner, and Fred McDowell. They have multiple Grammy® nominations for their acclaimed experimental albums, and the latest album, Still Shakin’, is out now.
The 91-year-old Bobby Rush is a three-time Grammy Award® winner for “Best Traditional Blues Album” for Porcupine Meat, Rawer than Raw, and 2024’s All My Love for You. He is also a 16-time Blues Music Awards winner (with 56 career nominations) and has been inducted into the Blues Hall of Fame, Mississippi Musicians Hall of Fame and Rhythm & Blues Hall of Fame.

THIRD PARTY RESELLERS
Don’t get taken by deceptive online resellers who use bots to buy tickets and then mark up their prices. The only safe way to protect your purchase and guarantee the best seats at the lowest cost is to work directly with us: through our website, by phone, or at our box office in Santa Rosa. Plus, we’re not bots. Our friendly team members are easily accessible by phone or at the box office to provide customer support.

MOTHER'S DAY BRUNCH - ORSI FAMILY VINEYARDS ~ STAY HEALDSBURG
2026-05-10 11:00 - 13:00
Event
Mother’s Day Brunch

Orsi Family Vineyards · Healdsburg, CA

Join us for a relaxed, Italian-style brunch featuring four of our favorite pours—Sparkling Biancolella, Fiano, Nebbiolo, and Sangiovese.
Wine club members enjoy $15 off—call or email us to receive your code.
We look forward to welcoming you and your family for a lively afternoon of great wine, delicious bites, and live music!

Private Events
If you are interested in learning more about our offerings, please fill out the request form and we will contact you to discuss details.
Request information
More information

Orsi Family Vineyards
2306 Magnolia Drive
Healdsburg, CA 95448
Parking: On-site, street parking
+1 707-732-4660
http://www.orsifamilyvineyards.com

Event details

Sunday, May 10, 2026
11:00 AM – 1:00 PM
$85 per ticket

Orsi Family Vineyards
2306 Magnolia Drive
Healdsburg, CA 95448

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TACO TUESDAYS! ~ STAY HEALDSBURG
2026-05-12 16:00 - 18:00
Taco Tuesdays!

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Name: Taco Tuesdays!

Date: May 12, 2026
Time: 4:00 PM – 6:00 PM PDT

Event Description:

Taco Tuesday! Weekly Taco pop up with live music.

Event Media:

To Current Calendar

Location:

Dry Creek General Store
3495 Dry Creek Road, Healdsburg Ca

Date/Time Information:

4pm-6pm

Contact Information:

Send an Email

Fees/Admission:

Free

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TACO TUESDAYS! ~ STAY HEALDSBURG
2026-05-12 16:00 - 18:00
Taco Tuesdays!

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Name: Taco Tuesdays!

Date: May 12, 2026
Time: 4:00 PM – 6:00 PM PDT

Event Description:

Taco Tuesday! Weekly Taco pop up with live music.

Event Media:

To Current Calendar

Location:

Dry Creek General Store
3495 Dry Creek Road, Healdsburg Ca

Date/Time Information:

4pm-6pm

Contact Information:

Send an Email

Fees/Admission:

Free
