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THE YALE WHIFFENP00FS AT THE RAVEN THEATER ~ STAY HEALDSBURG
2025-10-19 19:00 - 22:00 (America/New_York)
The Yale Whiffenpoofs at The Raven Theater
October 19, 2025 @ 7:00 pm – 10:00 pm
The Raven Performing Arts Theater

The Yale Whiffenpoofs at The Raven Theater
America’s oldest collegiate a cappella group, the Yale Whiffenpoofs are coming to the Raven, featuring Healdsburgian Tabatha Mireya Stewart!
Every year, 14 Yale seniors are selected to be in the Whiffenpoofs, the world’s oldest and best-known collegiate a cappella group. Founded in 1909, the “Whiffs” began as a senior quartet that met for weekly concerts at Mory’s Temple Bar, the famous Yale tavern. They were all-male until 2019, but the group now includes female students as well. Over the years, the Whiffs have appeared all over the world. See them on October 19th!
Sunday, October 19th. 7:00PM – 10:00PM.
Gold: Center section front rows: $44
General Admission: $29
Student: $14
Prices include all fees.
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CHRISTY LYNN RIBB0N CUTTING ~ STAY HEALDSBURG
2025-10-22 10:00 - 10:30
Christy Lynn Ribbon Cutting
October 22, 2025 @ 10:00 am – 10:30 am
Christy Lynn

You’re invited to celebrate the ribbon cutting of Christy Lynn’s first California boutique, located in the heart of downtown Healdsburg on Wednesday, October 22nd.

Be among the first to experience the timeless elegance and romantic craftsmanship of Christy Lynn. Following the ribbon-cutting ceremony, enjoy shopping, light refreshments, and an exclusive look at the Fall collection inside the stunning new boutique.

Come celebrate this exciting new chapter in Healdsburg’s luxury fashion scene!

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SCREAM ~ STAY HEALDSBURG
2025-10-23 19:00 - 21:30
Wednesday, October 23 & Thursday, October 24

Scream

1996 | USA | 1hr 52min | Rated NR

A year after the murder of her mother, a teenage girl is terrorized by a masked killer who targets her and her friends by using scary movies as part of a deadly game. Directed by Wes Craven. Written by Kevin Williamson. With David Arquette, Neve Campbell, Courtney Cox, Rose McGowan, Matthew Lillard, and Drew Barrymore.

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IC0N C0NCERTS PRESENTS ~ STEVE TREVIN0: THE G00D LIFE T0UR - STAY HEALDSBURG
2025-10-24 20:00 - 22:00
ICON Concerts Presents
Steve Trevino: The Good Life Tour

Rescheduled Date: Friday, October 24, 2025
The previous performance date was Saturday, February 22, 2025

8:00 pm

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Comedian Steve Treviño is “America’s Favorite Husband.” He can “speak wife fluently,” never calls “the guys” for help on a home project and knows better than to “make his own decisions,” since decision-making is a privilege reserved solely for his wife, Renae. Treviño’s relatable approach to comedy affirms his status as one of the country’s fastest-rising comics. He has been viewed over 223 million times online, sold out shows coast to coast, amassed more than 2 million total social media followers, and headlined specials for Amazon, Netflix, Showtime, and more.
Treviño’s first Showtime special, Grandpa Joe’s Son, staked out a spot on the Nielsen Top 20. He also funded, produced, and shot his 2014 runaway Netflix hit, Relatable. To promote the special, he uploaded a clip titled, When Your Wife Comes Home from Shopping, which generated 56 million views on Facebook. It paved the way for popular clips, such as When You Ask Your Wife if She Wants McDonald’s (21 million views) and When Going to Vegas With Your Wife Goes Wrong (4 million views).
In 2020, Treviño and Renae unveiled a joint, weekly podcast entitled, Steve Treviño and Captain Evil, that has generated over 1.5 million views/streams and is now in Season 3. He also filmed his fourth self-produced comedy special, My Life in Quarantine, which was picked up by Amazon Prime. His self-produced fifth special, I Speak Wife, independently released on Friday, October 21, for free viewing exclusively for his global audience on YouTube.
Ages 12 & Up

IC0N C0NCERTS PRESENTS: STEVE TREVINO: THE G00D LIFE T0UR - STAY HEALDSBURG
2025-10-24 20:00 - 22:00
ICON Concerts Presents
Steve Treviño: The Good Life Tour

Rescheduled Date: Friday, October 24, 2025
The previous performance date was Saturday, February 22, 2025

8:00 pm

BUY TICKETS

Comedian Steve Treviño is “America’s Favorite Husband.” He can “speak wife fluently,” never calls “the guys” for help on a home project and knows better than to “make his own decisions,” since decision-making is a privilege reserved solely for his wife, Renae. Treviño’s relatable approach to comedy affirms his status as one of the country’s fastest-rising comics. He has been viewed over 223 million times online, sold out shows coast to coast, amassed more than 2 million total social media followers, and headlined specials for Amazon, Netflix, Showtime, and more.
Treviño’s first Showtime special, Grandpa Joe’s Son, staked out a spot on the Nielsen Top 20. He also funded, produced, and shot his 2014 runaway Netflix hit, Relatable. To promote the special, he uploaded a clip titled, When Your Wife Comes Home from Shopping, which generated 56 million views on Facebook. It paved the way for popular clips, such as When You Ask Your Wife if She Wants McDonald’s (21 million views) and When Going to Vegas With Your Wife Goes Wrong (4 million views).
In 2020, Treviño and Renae unveiled a joint, weekly podcast entitled, Steve Treviño and Captain Evil, that has generated over 1.5 million views/streams and is now in Season 3. He also filmed his fourth self-produced comedy special, My Life in Quarantine, which was picked up by Amazon Prime. His self-produced fifth special, I Speak Wife, independently released on Friday, October 21, for free viewing exclusively for his global audience on YouTube.
Ages 12 & Up

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.

THE SWEET TASTE 0F THE HARVEST: FALL F00DS W0RKSH0P - STAY EALDSBURG
2025-10-25 14:00 - 16:00
Sweet Taste of the Harvest: Fall Foods Workshop
October 25, 2025 @ 2:00 pm – 4:00 pm

Sweet Taste of the Harvest: Fall Foods Workshop
On Saturday, October 25, from 2 to 4 p.m., h2hotel invites guests to celebrate the bounty of Sonoma’s fall harvest with its Sweet Taste of the Harvest: Fall Foods Workshop. Led by Lisal Moran of Parker Hill Provisions, participants will craft three seasonal treats – Fall Fruit Zeppole, Cabernet Granita, and Spiced Pumpkin Butter – while learning tips on preserving fall produce, pairing ingredients with seasonal flair, and adding a touch of gourmet to their pantry staples.
Guests will take home their jar of spiced pumpkin butter, a packet of recipes, and new culinary know-how to bring the taste of Sonoma’s harvest into their own kitchens. Local wine and non-alcoholic beverages will be served to complement the experience.
Tickets are $150 per person and can be purchased via Eventbrite.
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SWEET TASTE 0F THE HARVEST: FALL F00DS W0RKSH0P ~ STAY HEALDSBURG
2025-10-25 14:00 - 16:00

GRAND 0PENING BL0CK PARTY! - STAY HEALDSBURG
2025-10-25 14:00 - 17:00
Saturday, October 25, 2:00 – 5:00 pm
Grand Opening Block Party!

Calling our friends and neighbors!
Please join us to celebrate the Grand Opening of True West Cinemas with a festive and free block party. Catch curated short film programs, and enjoy popcorn, concessions samples, live music, and more. Free and open to the community.
After the party, join us in the cinemas to enjoy a free screening of Coco.
5:30 p.m. — Coco, in Spanish language
8:00 p.m. — Coco, with Spanish subtitles

Reserve Free Tickets for Coco

GRAND 0PENING BL0CK PARTY! ~ STAY HEALDSBURG
2025-10-25 14:00 - 17:00
Buy Tickets Now

Saturday, October 25, 2:00 – 5:00 pm
Grand Opening Block Party!

Please join us to celebrate the Grand Opening of True West Cinemas with a festive and free block party. Catch curated short film programs, and enjoy free popcorn, concessions samples, games, and more. Free and open to the community.
After the party, join us in the cinemas for a free screening of Coco. Standby tickets may be available at the door.
5:30 p.m. — Coco, in Spanish
8:00 p.m. — Coco, with Spanish subtitles

Reserve Free Tickets for Coco

THE UNI EXPERIENCE ~ STAY HEALDSBURG
2025-10-25 15:00 - 17:00
The UNI Experience
October 25, 2025 @ 3:00 pm – 5:00 pm
Truett Hurst Tasting Barn

Want to save the environment, just by eating the problem?
On October 25th, learn about the environmental impact of Sea Urchins directly from expert divers, all while enjoying them as a fresh-caught delicacy with fantastic wine.
Join us for a truly adventurous, delicious, and educational evening led by professional Urchin divers Gary and Tom Trumper. The father-son duo will be presenting UNI served several ways, educating attendees about their work in urchin research. Enjoy curated wine selections that pair delightfully with the presentation.
Special guest Dave Rudie, Chairman of the board of the California Sea Urchin Commission, will present educational information about Urchins as invasive species and the benefits of removing them from ecosystems.
This event takes place at our tasting room at 428 Hudson Street.
$30 general admission
$15 for Truett Hurst & VML members
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This event is 21+. While we love your furry friends, please leave dogs at home for this event.
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C0C0 ~ STAY HEALDSBURG
2025-10-25 17:00 - 20:00
Saturday, October 25

Coco

2017 | USA | 1hr 45min | Rated PG
Free Screenings – True West Cinemas

Despite his family’s baffling generations-old ban on music, Miguel dreams of becoming an accomplished musician like his idol, Ernesto de la Cruz. Desperate to prove his talent, Miguel finds himself in the stunning and colorful Land of the Dead following a mysterious chain of events. Along the way, he meets charming trickster Hector, and together, they set off on an extraordinary journey to unlock the real story behind Miguel’s family history. Free tickets required. With Anthony Gonzalez, Gael García Bernal, Benjamin Bratt, Alanna Ubach, and Renée Victor.

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ENCANT0 ~ STAY HEALDSBURG
2025-10-25 18:30 - 21:00
Saturday, October 25

Encanto

2021 | USA | 1h 42m | Rated PG
Free Outdoor Screening – Cloverdale City Park
Presented in partnership with Cloverdale Youth Soccer

An extraordinary family, the Madrigals, live hidden in the mountains of Colombia, in a magical house called an Encanto. The magic of Encanto has blessed every child in the family with a unique gift – every child except one, Mirabel. With Stephanie Beatriz, María Cecilia Botero, and John Leguizamo.

KATHLEEN MADIGAN: THE DAY DRINKING T0UR - STAY HEALDSBURG
2025-10-25 19:30 - 21:30
Kathleen Madigan: The Day Drinking Tour

October 25, 2025
Revised Show Time of 7:30 pm

Comedian Kathleen Madigan’s 33-year comedy career is showing no signs of slowing down from The Potluck Party Tour in 2024 and The Day Drinking Tour in 2025. As a premiere stand-up comedian, Madigan sells out marquee theaters across the country and is one of the few female comedians to tour over 250 days a year. Madigan has squeezed in more than 40 appearances on daytime and late-night talk shows and has had comedy specials premiere on Netflix, Comedy Central, MAX and Amazon Prime Video. She has also appeared on Jerry Seinfeld’s popular Netflix series, Comedians in Cars Getting Coffee, and hosts her popular weekly podcast, Madigan’s Pubcast, which currently has over 10.7 million downloads on all streaming outlets.

KATHLEEN MADIGAN THE DAY DRINKING T0UR - STAY HEALDSBURG
2025-10-25 19:30 - 21:30
Kathleen Madigan
The Day Drinking Tour

Saturday, October 25, 2025

7:30 pm

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Comedian Kathleen Madigan’s 33-year comedy career is showing no signs of slowing down, from The Potluck Party Tour in 2024 and The Day Drinking Tour in 2025. As a premiere stand-up comedian, Madigan sells out marquee theaters across the country and is one of the few female comedians to tour over 250 days a year. Madigan has squeezed in more than 40 appearances on daytime and late-night talk shows and has had comedy specials premiere on Netflix, Comedy Central, MAX and Amazon Prime Video. She has also appeared on Jerry Seinfeld’s popular Netflix series, Comedians in Cars Getting Coffee, and hosts her popular weekly podcast, Madigan’s Pubcast, which currently has over 10.7 million downloads on all streaming outlets.

KATHLEEN MADIGAN THE DAY DRINKING T0UR - STAY HEALDSBURG
2025-10-25 19:30 - 21:30
Kathleen Madigan
The Day Drinking Tour

Saturday, October 25, 2025

7:30 pm

BUY TICKETS

Comedian Kathleen Madigan’s 33-year comedy career is showing no signs of slowing down, from The Potluck Party Tour in 2024 and The Day Drinking Tour in 2025. As a premiere stand-up comedian, Madigan sells out marquee theaters across the country and is one of the few female comedians to tour over 250 days a year. Madigan has squeezed in more than 40 appearances on daytime and late-night talk shows and has had comedy specials premiere on Netflix, Comedy Central, MAX and Amazon Prime Video. She has also appeared on Jerry Seinfeld’s popular Netflix series, Comedians in Cars Getting Coffee, and hosts her popular weekly podcast, Madigan’s Pubcast, which currently has over 10.7 million downloads on all streaming outlets.

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.

DIA DE MUERT0S - STAY HEALDSBURG
2025-10-26 12:00 - 18:00
Dia De Muertos
October 26, 2025 @ 12:00 pm – 6:00 pm
Healdsburg Plaza

Dia De Muertos
Saturday, October 26 | Healdsburg Plaza
Presented by Corazón Healdsburg in partnership with the City of Healdsburg
Join us for a vibrant and heartfelt celebration of Día de Muertos at the Healdsburg Plaza on Saturday, October 26. Hosted annually by Corazón Healdsburg in collaboration with the City of Healdsburg, this cherished community event honors the rich traditions of this beloved holiday, where families come together to remember and celebrate the lives of loved ones who have passed.
The event features a stunning, marigold-adorned community altar where guests are invited to leave photos or mementos in tribute. The day will be filled with live music performances, a classic car show, food vendors, face painting, games and crafts for children, and interactive cultural activities that celebrate heritage and community.
With over 5,000 attendees each year, the Día de Muertos celebration is one of Healdsburg’s most beloved cultural gatherings—offering a beautiful space for remembrance, joy, and connection.
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DIA DE MUERT0S ~ HEALDSBURG PLAZA - STAY HEALDSBURG
2025-10-26 12:00 - 18:00

DIA DE MUERT0S - HEALDSBURG PLAZA - STAY HEALDSBURG
2025-10-26 12:00 - 18:00
