Wine Country Life Vacation Homes

NET ST0P C0MEDY @ CRAFTW0RK HEALDSBURG - STAY HEALDSBURG
2025-11-21 19:00 - 21:00 (America/New_York)
Next Stop Comedy @ CraftWork Healdsburg
November 21, 2025 @ 7:00 pm – 9:00 pm
CraftWork Healdsburg

Next Stop Comedy @ CraftWork Healdsburg
Next Stop Comedy is coming to CraftWork Healdsburg!
Get ready for an unforgettable night of laughter as top comedians from across the country bring their best sets straight to your neighborhood. Each show features a brand-new lineup, so no two nights are ever the same. Whether you’re planning a fun date night, catching up with friends, or just in need of some serious laughs, Next Stop Comedy delivers high-energy performances, great vibes, and a night you won’t want to miss.
Join us at CraftWork Healdsburg for comedy, community, and plenty of reasons to smile. Wine will be available for purchase throughout the evening, and there’s no drink minimum.
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NEXT ST0P C0MEDY @ CRAFTW0RK HEALDSBURG ~ STAY HEALDSBURG
2025-11-21 19:00 - 21:00

NEXT ST0P C0MEDY @ CRAFTEW0RK HEALDSBURG ~ STAY HEALDSBURG
2025-11-21 19:00 - 21:00

THANKSGIVING IN HEALDSBURG WITH AUTH0R SARA CALV0SA 0LS0N ~ STAY HEALDSBURG
2025-11-21 19:00 - 21:00
Thanksgiving in Healdsburg with Author Sara Calvosa Olson
November 21, 2025 @ 7:00 pm
The 222

Award-winning Karuk author and food writer Sara Calvosa Olson presents her cookbook Chími Nu’am: Native California Foodways for the Contemporary Kitchen—and for this special event she brings her insights to Wine Country. Olson explores the indigenous food systems of California, re-imagining ancestral ingredients and cooking techniques for modern home cooks. Her journey weaves together narrative, heritage, and practice, with stories of acorn preparation, traditional proteins, wild forage, and mindful sourcing. The evening will include samples of select dishes, making it a sensory as well as an intellectual experience.
With a nod to the holiday season, Thanksgiving in Healdsburg is more than a talk—it’s an invitation to appreciate the land, celebrate heritage, and enjoy food in community. Reserving early is strongly encouraged.
Thanksgiving in Healdsburg Author Event Details

Tickets: $20 general admission (available online)
Run time: Approximately 120 minutes (no intermission)
222 Healdsburg is ground-level and ADA-accessible; parking available nearby.
Sampling of native foods included
Wine and beverages available for purchase—arrive early to get settled.

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TINSLEY ELLIS - THE ''NAKED TRUTH'' T0UR! - STAY HEALDSBURG
2025-11-21 19:30 - 22:00
Tinsley Ellis – The “Naked Truth” Tour!
November 21, 2025 @ 7:30 pm – 10:00 pm
The Raven Performing Arts Theater

Tinsley Ellis – The “Naked Truth” Tour! at The Raven Theater
According to Atlanta-based blues guitarist, singer and songwriter Tinsley Ellis, his new, first-ever solo acoustic album, Naked Truth, is both “a departure and an arrival.” Ellis has been recording and travelling the world for over four decades, delivering his feral, guitar-fueled, original electric blues-rock to ever-growing audiences at concert halls, festivals, and clubs. Naked Truth is steeped in the folk blues traditions of Muddy Waters, Skip James, Son House, Robert Johnson and even Leo Kottke. To the casual fan, this might seem to be a new direction, but for Ellis, it’s an extension of his music, as he taps into the raw essence of the blues. “This is a record I’ve always wanted to make, and one that my longtime fans have been asking for,” he says, noting he’s included an acoustic mini-set in his concert performances for years. In the last 12 months, Ellis has already performed over 100 solo shows, many as co-bills with his Alligator label-mate Marcia Ball. “I’m having so much fun playing these shows,” he says.
Friday, November 21st. 7:30PM – 10:00PM.
Admission: $29 – $39 (includes fees).
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TINSLEY ELLIS - THE ''NAKED TRUTH'' T0UR! ~ STAY HEALDSBURG
2025-11-21 19:30 - 22:00

HARVEST CELEBRATI0N & H0LIDAY 0PEN H0USE AT BRICK & M0RTAR ~ STAY HEALDSBURG
2025-11-22 14:00 - 17:00
Harvest Celebration & Holiday Open House at Brick & Mortar
November 22, 2025 @ 2:00 pm – 5:00 pm
Brick & Mortar Wines

Raise a glass with Brick & Mortar Wines at a festive Harvest Celebration on November 22, from 2 to 5 p.m. The winery swings open its doors for an afternoon of discovery, featuring four fellow boutique producers who also craft their wines at the Brick & Mortar facility. Guests can taste an array of small-lot releases, chat with the winemakers and founders, and pick up bottles perfect for upcoming holiday gatherings. Complimentary for Brick & Mortar list members and friends, this laid-back celebration blends great wine, good company, and true Wine Country camaraderie.
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DJANG0 FESTIVAL ALLSTARS ~ STAY HEALDSBURG
2025-11-22 19:00 - 21:30
Django Festival Allstars
November 22, 2025 @ 7:00 pm – 9:30 pm
The Raven Performing Arts Theater

Django’s unmistakable cool and jumpin’ joie de vivre have made him an icon for an unlikely range of luminaries from Carlos Santana to Eric Clapton, guitar greats! Jimi Hendrix named his “big band of gypsies” in tribute, and Willie Nelson adopted his influence in “country-swing.”
The Django Festival Allstars have grown into a brilliantly cohesive group of star musicians who’ve taken America by storm, performing at top concert halls and festivals to standing ovations. They’ve appeared at SFJazz, Kennedy Center, Dizzy’s and Rose Hall, Jazz@Lincoln Center, Keystone Korner, Hollywood Bowl, Montreal Jazz Festival and Arts Centers, Kimmel, Strathmore, and many more, including Carnegie Hall and Birdland (for 25 years).
The music speaks of Paris in the 20s and 30s when “gitane” music filled the air, in the cafés, the streets, in the countryside, a romantic Paris with lovers, campfires, a time of Montmartre, la belle époque, le Boudon café, café au lait, luscious pastry, and a great glass of wine. Django was “king’.” He teamed with Jazz Violinist Stephane Grappelli and made musical history.
The Django Festival Allstars bring this music to today… combining known standards and original music…intoxicating!! They swing like crazy and will break your heart with a ballad. Their special guests have been Randy Brecker, Joe Lovano, Regina Carter, Cyrille Aimee, Ken Peplowski, Madeleine Peyroux, Sefon Harris, James Carter, to name a few.
Saturday, November 22nd, 7PM.
Admission: $28 – $103.
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THE STRAY CATS - STAY HEALDSBURG
2025-11-22 20:00 - 22:00
The Stray Cats

Saturday, November 22, 2025

8:00 pm

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The Stray Cats, the band that put Rockabilly music back on the record charts in the early ’80s, scored several big hits on both sides of the Atlantic. All thanks to genuine musical chops that evoke the best players of rockabilly’s original heyday and a striking visual 1950’s style made contemporary with exaggerated pompadours and colorful tattoos.

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.

LIVE NATI0N PRESENTS - NATE JACKS0N - BIG D0G - STAY HEALDSBURG
2025-11-23 20:00 - 22:00
Live Nation Presents
Nate Jackson: BIG DOG

Sunday, November 23, 2025

8:00 pm

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Nate Jackson’s popularity has exploded with one of the fastest growing fan bases through viral content. His remarkable engagement on TikTok has earned more than 3 million followers and more than 500 million views globally. Jackson is a comedian, actor, writer, and digital creator who sells out comedy clubs and theatres across America.
Age Limit 16+

VIP 1: GUARANTEED ROAST ZONE – ONLY

Best 4 seats front and center
Include a guarantee to be roasted

VIP 2: ROAST ZONE

Best seats closest to stage

ADD-ON: MEET & GREET TO VIP PACKAGE – Limited Quantity Available

Pre-show Meet & Greet with Nate Jackson

LIVE NATI0N PRESENTS: NATE JACKS0N: BIG D0G - STAY HEALDSBURG
2025-11-23 20:00 - 22:00
Live Nation Presents
Nate Jackson: BIG DOG

Sunday, November 23, 2025

8:00 pm

BUY TICKETS

Nate Jackson’s popularity has exploded with one of the fastest growing fan bases through viral content. His remarkable engagement on TikTok has earned more than 3 million followers and more than 500 million views globally. Jackson is a comedian, actor, writer, and digital creator who sells out comedy clubs and theatres across America.
Age Limit 16+

VIP 1: GUARANTEED ROAST ZONE – ONLY

Best 4 seats front and center
Include a guarantee to be roasted

VIP 2: ROAST ZONE

Best seats closest to stage

ADD-ON: MEET & GREET TO VIP PACKAGE – Limited Quantity Available

Pre-show Meet & Greet with Nate Jackson

All Meet and Greet packages are non-transferable; no name changes will be permitted. No refunds or exchanges; all sales are final.

Platinum Tickets are tickets that are dynamically priced up and down based on demand. Platinum Tickets are not part of VIP packages – they are tickets only.
Platinum Seating provides fans with direct access to securing some of the best seats in the venue at market value. The market value for Platinum Seating is subject to change based on the overall demand and popularity for the event. Platinum Seating allows fans to purchase tickets in a safe and secure environment without running the risk of purchasing tickets that may be considered lost, stolen, or counterfeit.

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.

LIVE NATI0N PRESENTS NATE JACKS0N: BIG D0G - STAY HEALDSBURG
2025-11-23 20:00 - 22:00

HEALDSBURG TURKEY TR0T - STAY HEALDSBURG
2025-11-27 08:00 - 09:30
Healdsburg Turkey Trot
November 27, 2025 @ 8:00 am – 9:30 am
Start and Finish at Healdsburg Running Company

What started as a humble fun run has evolved into an all-out Healdsburg tradition, raising funds for scholarships that help students overcome financial barriers and attend college. Presented by the Rotary Club of Healdsburg Sunrise and the Healdsburg Running Company, and in partnership with the City of Healdsburg, this community-driven event brings together locals and visitors, all rallying for a great cause—LIVE LIKE DREW. The Healdsburg Turkey Trot gives our students a real boost by recognizing and supporting Healdsburg’s high-achieving Scholar-Athletes. Together we help them move one step closer to their dreams.
Kicking off on Thanksgiving morning at 8:00, the Turkey Trot invites everyone – from competitive runners to families with strollers, and even furry friends – to join in on the 5K fun. Expect a lively crowd of 3,000 to 4,000 runners, walkers, and participants decked out in costumes, festive hats, and even turkey feathers. And our beloved City Council Member, David Hagele, will be spinning tunes from the DJ table, bringing a dance-party vibe to the start and finish lines!
“The Turkey Trot is more than a race; it’s a full-on community party,” said Skip Brand, Race Director. “From everyone singing the national anthem together to the costumes, live music, and dance breaks, this is a quintessential slice of Americana. It’s about celebrating, giving thanks, and having a blast together.”
The Healdsburg Turkey Trot remains one of the most accessible and inclusive events in the region, keeping costs affordable and offering free entries to those in need. This commitment to inclusion means everyone – locals, visitors, and participants from all over Sonoma County – can feel the warmth of Healdsburg’s community spirit.
Race participants will enjoy professionally timed results and commemorative shirts. Top runners can look forward to exciting prizes, including fresh-baked pies from Costeaux French Bakery. And everyone who joins can feel proud of giving back in a meaningful way.
Sponsors including Big John’s Market, Charlie Palmer Pigs ‘n Pinot, Stay Healdsburg, Rio Lindo Academy, Healthcare Foundation Northern Sonoma County, Preston Family Charitable Fund, and many other local businesses are instrumental in making this event possible. Thanks to their support, the Turkey Trot continues to raise crucial funds for scholarships and other essential community efforts such as Healdsburg High School Interact Club, Healdsburg High Greyhound Boosters, Farm to Fight Hunger, Reach for Home, and Healdsburg Sunrise Rotary Ideals Scholarships.
Ready to lace up and join the fun? Head to www.5ktrot.com to register and get all the event details. Whether you’re running, walking, or simply grooving to the music, join us Thanksgiving morning for a day full of heart, health and Healdsburg cheer.
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HEALDSBURG TURKEY TR0T ~ STAY HEALDSBURG
2025-11-27 08:00 - 09:30
Healdsburg Turkey Trot
November 27, 2025 @ 8:00 am – 9:30 am
Start and Finish at Healdsburg Running Company

Healdsburg Turkey Trot
What started as a humble fun run has evolved into an all-out Healdsburg tradition, raising funds for scholarships that help students overcome financial barriers and attend college. Presented by the Rotary Club of Healdsburg Sunrise and the Healdsburg Running Company, and in partnership with the City of Healdsburg, this community-driven event brings together locals and visitors, all rallying for a great cause—LIVE LIKE DREW. The Healdsburg Turkey Trot gives our students a real boost by recognizing and supporting Healdsburg’s high-achieving Scholar-Athletes. Together we help them move one step closer to their dreams.
Kicking off on Thanksgiving morning at 8:00, the Turkey Trot invites everyone – from competitive runners to families with strollers, and even furry friends – to join in on the 5K fun. Expect a lively crowd of 3,000 to 4,000 runners, walkers, and participants decked out in costumes, festive hats, and even turkey feathers. And our beloved City Council Member, David Hagele, will be spinning tunes from the DJ table, bringing a dance-party vibe to the start and finish lines!
“The Turkey Trot is more than a race; it’s a full-on community party,” said Skip Brand, Race Director. “From everyone singing the national anthem together to the costumes, live music, and dance breaks, this is a quintessential slice of Americana. It’s about celebrating, giving thanks, and having a blast together.”
The Healdsburg Turkey Trot remains one of the most accessible and inclusive events in the region, keeping costs affordable and offering free entries to those in need. This commitment to inclusion means everyone – locals, visitors, and participants from all over Sonoma County – can feel the warmth of Healdsburg’s community spirit.
Race participants will enjoy professionally timed results and commemorative shirts. Top runners can look forward to exciting prizes, including fresh-baked pies from Costeaux French Bakery. And everyone who joins can feel proud of giving back in a meaningful way.
Sponsors including Big John’s Market, Charlie Palmer Pigs ‘n Pinot, Stay Healdsburg, Rio Lindo Academy, Healthcare Foundation Northern Sonoma County, Preston Family Charitable Fund, and many other local businesses are instrumental in making this event possible. Thanks to their support, the Turkey Trot continues to raise crucial funds for scholarships and other essential community efforts such as Healdsburg High School Interact Club, Healdsburg High Greyhound Boosters, Farm to Fight Hunger, Reach for Home, and Healdsburg Sunrise Rotary Ideals Scholarships.
Ready to lace up and join the fun? Head to www.5ktrot.com to register and get all the event details. Whether you’re running, walking, or simply grooving to the music, join us Thanksgiving morning for a day full of heart, health and Healdsburg cheer.
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