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Last updated: November 11, 2024


Find your holiday joy in Cupertino with our detailed event guide. From Cupertino natives to wandering adventurers, our guide ensures a holiday season to cherish.

Popular events abound during this festive season, including the enchanting Winter Wonderland at the Tilden Park Merry Go Round, where families can enjoy classic carousel rides adorned with holiday lights. This year features cozy gatherings and delightful snacks for all ages. Holidays in the Park at Six Flags Discovery Kingdom offers thrilling rides complemented by festive decorations that create a unique celebration of the season. And the Holiday Magic at Gilroy Gardens is something you definitely don’t want to miss, with its spectacular display of lights and charming holiday experiences throughout the garden. See more details on these and other fun events and activities below!

Contact information and details below.



Cupertino Holiday Light Displays


What to Expect:

Vintage train cars decorated with thousands of colorful lights.

Description:

The Holiday Lights Train by Roaring Camp Railroads features vintage excursion cars adorned with thousands of colorful lights, rolling through Santa Cruz city streets past homes. Live music by Steve Bennett and visits with Santa Claus and his elves add to the festive atmosphere.

Where: Felton | More Info: Holiday Lights Train - Roaring Camp

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What to Expect:

Immersive holiday light displays and unique seasonal activities.

Description:

Filoli Holidays features a stunning display of 3,600 strands of lights, a 210-foot-long light tunnel, and over 7,000 ornaments. The event includes daytime and evening admissions, festive music, carolers, and various seasonal activities like holiday teas and private fire pit experiences.

Where: Woodside | More Info: Filoli Holidays

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What to Expect:

Holiday celebration with twinkling lights and cultural activities.

Description:

Fairy Winterland at Children's Fairyland in Oakland, California, features twinkling lights, festive music, and holiday crafts. Enjoy candle making, hot cocoa, and apple cider while exploring the park's culturally diverse holiday displays.

Where: Oakland | More Info: Fairy Winterland

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What to Expect:

Holiday light display in a historic cemetery setting.

Description:

Twinkling lights at Mountain View Cemetery feature a festive display of holiday scenes, including Santa's workshop, reindeer sleds, and playful penguins. The event is set against a backdrop of hundreds of tiny bright lights outlining the buildings and trees.

Where: Mountain View | More Info: Twinkling lights at the Mountain View Cemetery

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Cupertino Holiday Shows and Entertainment


What to Expect:

Immersive holiday experience with interactive activities and festive entertainment.

Description:

Gilroy Gardens transforms into a holiday destination with North Pole Nights, featuring jolly characters, live shows, ice skating, a grand feast, Santa's Workshop, and magical light displays.

Where: Gilroy | More Info: Holiday Magic - Gilroy Gardens

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What to Expect:

World-class ballet performance with elaborate sets and costumes inspired by 1905 San Jose.

Description:

The San Jose Nutcracker is a unique holiday ballet set in 1905 San Jose, featuring swirling snowflakes, waltzing flowers, and Tchaikovsky's immortal score. It celebrates the heritage that has made Santa Clara Valley a center of innovation.

Where: San Jose | More Info: The Nutcracker - Symphony San Jose

Event Organizer?

What to Expect:

Holiday ballet performance with period-inspired costumes and scenic elements.

Description:

The San Jose Nutcracker is a unique holiday production set in 1905 San Jose, featuring swirling snowflakes, waltzing flowers, and Tchaikovsky's immortal score. It celebrates the heritage that has made Santa Clara Valley the center of innovation.

Where: San Jose | More Info: The San Jose Nutcracker - Symphony San Jose

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What to Expect:

Heartwarming holiday musical with iconic Dr. Seuss characters.

Description:

Dr. Seuss' beloved holiday tale, How the Grinch Stole Christmas, comes to life on stage with hit songs "You're A Mean One, Mr. Grinch" and "Welcome Christmas." Max the Dog narrates as the Grinch, whose heart is two sizes too small, decides to steal Christmas from the holiday-loving Whos. Magnificent sets and costumes inspired by Dr. Seuss' original illustrations transport audiences to Whoville, while the music and book breathe new life into this timeless story of the true meaning of Christmas.

Where: San Jose | More Info: How The Grinch Stole Christmas - Broadway San Jose

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What to Expect:

Heartwarming performances by local talent and Santa's grand entrance.

Description:

The Christmas Tree Lighting at City Center Bishop Ranch features heartwarming performances by the Monte Vista band, singers, and dancers. Santa makes a grand entrance, and the event includes visits with Santa on various dates throughout the holiday season.

Where: San Ramon | More Info: Christmas Tree Lighting - City Center Bishop Ranch

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What to Expect:

Free ice skating lessons for beginners.

Description:

The Safeway Holiday Ice Rink in Union Square presented by Kaiser Permanente offers outdoor ice skating and holiday festivities in downtown San Francisco. It features special events like Drag On Ice, Silent Skate, and Polar Bear Skate, as well as free Learn To Skate lessons for beginners.

Where: San Francisco | More Info: Union Square Ice Rink

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Cupertino Other Holiday Activities


What to Expect:

Antique carousel with hand-carved wooden animals and calliope-style music.

Description:

The Tilden Park Merry Go Round offers a charming antique carousel with hand-carved wooden animals, calliope-style music, and a snack bar serving hot chocolate, ice cream, and carnival food. It is pet-friendly and LGBTQ-friendly, with weather-dependent operating hours.

Where: Berkeley | More Info: Winter Wonderland - Tilden Park Merry Go Round

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What to Expect:

"Vibrant light displays and diverse entertainment options."

Description:

The Santa Cruz County Fairgrounds & Event Center transforms into a vibrant display of lights and colors, featuring various exhibits, animal shows, and entertainment options. Visitors can enjoy deep-fried artichoke hearts, giant corn dogs, and garlic fries, as well as explore the insect/reptile exhibit and model train display.

Where: Watsonville | More Info: Holiday Lights - Santa Cruz County Fairgrounds & Event Center

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What to Expect:

Immersive holiday celebration with exclusive drink specials and live DJs.

Description:

Thousands of cheerful Santas, elves, and holiday enthusiasts gather in San Francisco for a vibrant celebration featuring holiday-themed drinks, lively music, and festive atmosphere at various bars and venues.

Where: San Francisco | More Info: SantaCon

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