Events in Healdsburg, CA

Upcoming Events and Experiences

Shared by

joshh

Way Back Wednesday
SEP 3
WINDSOR BREWERY

Way Back Wednesday

700 Mitchell Lane, Windsor, CA
Thu, Sep 3, 2026

This caught my eye! Way Back Wednesday is back at the Windsor Brewery, and it's a fantastic opportunity for vintage car enthusiasts. From 5 to 7 PM, you can bring your vintage cars, trucks, and motorcycles to show off and enjoy a lively atmosphere filled with fellow car lovers. The event is free and perfect for the whole family, so gather everyone and see what unique vehicles are in your garage! Don't miss out on this retro-themed meetup where you can connect with others who share your passion for classic rides.

Weekly
Family Friendly
Outdoor Seating
Free
Available Wednesday →

Shared by

nickmiller

Clueless
SEP 2
THE MADRONA

Clueless

1001 Westside Road Healdsburg, CA
Wed, Sep 2, 2026

Check out this amazing outdoor movie screening of 'Clueless' on September 2nd! The event is set in a beautiful garden, creating a cozy and intimate atmosphere under the stars. Enjoy a lawn-seating experience with personal headphones and cozy blankets provided for your comfort. Each ticket includes admission to the event, popcorn, and a movie snack, along with a complimentary glass of wine. Plus, there will be an outdoor tasting lounge featuring @dancingsonoma and restaurant favorites and cocktails available for purchase. It's the perfect way to enjoy a classic film with friends in a relaxed setting!

Outdoor Seating
Entertainment
Happening Wednesday →

Shared by

scooter24

Prime Rib Thursday — Live Jazz
SEP 4
THE GOODNIGHT

Prime Rib Thursday — Live Jazz

113 Plaza Street Healdsburg, CA
Fri, Sep 4, 2026

This caught my eye! Every Thursday evening, the downstairs dining room transforms into a lively jazz venue, featuring a talented band that sets the perfect backdrop for an unforgettable dining experience. Chef David Lawrence's Prime Rib Thursday menu is the star of the show, starting with a refreshing Chopped Wedge Salad. The main event is the Herb-Butter Prime Rib Roast, served alongside fluffy popovers, creamy Yukon Gold potato purée, and a rich Charles Goodnight Bourbon porcini jus. To top it all off, indulge in a delightful Bananas Foster for dessert. It's the ideal way to unwind and enjoy a night filled with great music and exceptional food.

Weekly
Entertainment
Dinner
Date Night
Available Thursday →

Shared by

sarah.parker

Cherry Bomb: A Redhead Cabaret (54 Below)
SEP 3
54 BELOW

Cherry Bomb: A Redhead Cabaret (54 Below)

254 West 54th Street New York, NY
Thu, Sep 3, 2026
9:30 PM - 11:30 PM

This caught my eye! Join this fiery ensemble of redheads for 'Cherry Bomb: A Redhead Cabaret', a celebration of what makes redheads so unique; their spunk, determination, and hair of course! Don't miss these rising stars as they sing iconic redhead songs from the musical theatre catalog in this dazzling night out. The event features an impressive lineup of performers including Molly Blackburn, Sam Corry, Rylynn Davis, and many more, all showcasing their talents in a vibrant cabaret setting. The show will take place in-person at 54 Below, with an option to livestream for those who can't attend in person. It's a perfect night for cabaret lovers and anyone who appreciates the artistry of musical theatre.

In Person & Online
Happening Thursday →

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Shared by

katnip19

Anniversary Night on Roof 106
SEP 4
THE MATHESON

Anniversary Night On Roof 106

Roof 106
Fri, Sep 4, 2026
9:00 PM - 12:00 AM

You’ve gotta check out this special Anniversary Night on Roof 106! This Friday, we’re celebrating five amazing years at The Matheson with a fantastic rooftop party from 9PM to midnight. Expect a lively atmosphere with a DJ spinning great tunes, delicious drinks flowing, and an incredible view to enjoy the night. It’s the perfect way to toast to our journey and all the exciting moments ahead. Don’t miss this chance to celebrate with us and make some unforgettable memories under the stars!

Entertainment
Outdoor Seating
Rooftop
Date Night
Happening Friday →

Shared by

johnny5alive

Roof 106 Late-Night Happy Hour & DJ (September 4)
SEP 4
THE MATHESON

Roof 106 Late-Night Happy Hour & DJ (September 4)

Roof 106
Fri, Sep 4, 2026
9:00 PM - 12:00 AM

Gotta make plans for the Roof 106 Late-Night Happy Hour and DJ event! This special celebration is happening on September 4 from 9 PM to midnight, and it's the perfect way to enjoy the vibrant atmosphere of Roof 106. Join us for a night filled with great music and fantastic drinks. The rooftop lounge offers a stunning view, making it an ideal spot to unwind and celebrate. Whether you're looking to dance the night away or just enjoy the company of friends, this event promises to be a memorable experience. Don't miss out on the fun and excitement as we celebrate five amazing years of The Matheson!

Entertainment
Outdoor Seating
Happening Friday →

Shared by

mellowmike

Virtual Auction
SEP 11
OVLC

Virtual Auction

Online
Fri, Sep 11, 2026 - Mon, Sep 21, 2026
9:00 AM - 6:00 PM

The Virtual Auction is part of the Mountainfilm on Tour event, which has been a cherished gathering for the community for over a decade. This year, the auction runs from September 11 through September 21, providing a unique opportunity for everyone to participate and support the Ojai Valley Land Conservancy (OVLC). The auction features a variety of items and experiences that reflect the spirit of adventure and conservation. Alongside the auction, attendees can enjoy award-winning short films, live music, and delicious food from local food trucks during the main event on September 19. This is not just an auction; it's a chance to connect with the community and contribute to a meaningful cause. Don't miss out on this opportunity to bid on exciting items while supporting the preservation of the beautiful Ojai Valley. Check the link below for more information.

Online
Daily
Starting 09/11/26 →