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Winter events happening in and around San Jose, CA

Check out winter and holiday-themed events happening in and around San Jose, CA in this seasonal guide.

People ice skating hand-in-hand.

We’re ready for all of the winter activities this season.

Photo via Enchant

Table of Contents

Get your fuzzy socks and hot cocoa ready, San Jose. From light displays to holiday performances and festive parties, winter is where the great 408 thrives.

Gather the family and friends and celebrate what makes the holiday season special with this guide featuring 40+ winter events happening between December and January.

Festivals and markets

Enchant | Now-Sunday, Jan. 1 | Times vary | PayPal Park | $25-$33 | Skate through an icy trail, drink cocktails from an ice bar, and enjoy a themed maze of more than four million lights.

Christmas in the Park | Open daily through Sunday, Dec. 31 | Times vary | Plaza de Cesar Chavez | Free | The annual San Jose tradition returns with storytime displays, decorated trees, an inflatable beer garden, and of course, the snowman hot chocolate.

Winterfest | Through Sunday, Dec. 31 | Times vary | California’s Great America | $19.99-$49.99 | Enjoy more than 60 rides + holiday attractions across the decorated amusement park.

Yuletide ODDventure | Every Saturday through Dec. 30 | 12-9 p.m. | Winchester Mystery House | Shop for out-of-the-ordinary gifts with this market offering strange stocking stuffers, bugs, bones, antiques, and bizarre collectibles.

Carol of Lights | Saturday, Dec. 2 | 4-7 p.m. | Downtown Campbell | Free | Join in on the annual winter festival that features a visit from Santa, petting zoo, donkey rides, face painting, free snacks, and more — ugly holiday sweaters are encouraged.

Ugly Sweater Christmas Market + Toy Drive | Sunday, Dec. 3 | 1-6 p.m. | 30 Post St. | Free | Get some holiday shopping done at this market with food, music, makers + Santa Claus.

Fiesta Navideña | Friday, Dec. 8 | 5:30-10 p.m. | Mexican Heritage Plaza | Free | Hear music from Tres Souls, shop La Plaza’s Christmas-themed festival, and eat Mexican-inspired cuisine.

Creepmas | Sunday, Dec. 10 | 1-6 p.m. | 675 E. Empire St. | Free | Find unique, handmade gifts at this craft fair featuring “haunting” items.

San José Winter Wonder Market | Saturday, Dec. 16-Sunday, Dec. 17 | 11 a.m.-5 p.m. | Westgate Center | Free | Do your last-minute holiday shopping with a variety of 150+ makers, artists, designers, and small businesses.

Tamalada & Boutique | Monday, Dec. 18 | 9 a.m.-6 p.m. | Saint John Vianney Community Center | $5-$450 | Shop from a Christmas boutique, enjoy live music by Los Amigos, and join in on a Tamale-making class — all tamales will be gifted to farmworkers in Half Moon Bay.

Not Another Emo Xmas Ugly Sweater Party | Saturday, Dec. 23 | 6 p.m. | Camino Brewing Co. | Free | Shop from pop-ups Lovely Sexy, Dreamy Thrift, and Cabezones Art, listen to DJ sets from DJs Darling Cool + YouCantStopMike, and rock out with Voluntary Hazing.

Two kids pose with Santa.

It’s all smiles with Santa.

Fun for the little ones

Polar Play Days | Through Monday, Jan. 15, 2024 | Times vary | Tech Interactive | $28-$34 | Have some STEM-tastic fun with Polar-themed exhibits, play zones, winter activities, and IMAX Dome Theater thrills.

Cookies and Carols With Mrs. Claus | Saturday, Dec. 9 | 11 a.m.-1 p.m. | Eastridge Mall | $5 | The kiddos are welcome to decorate two cookies and enjoy stories + carols with Mrs. Claus.

Holiday Open House | Saturday, Dec. 9 | 12-3 p.m. | Los Lagos Golf Course | Free | Hot cocoa, chocolate cookies, face painting, horse-drawn carriage rides, and Santa pictures await.

Children’s Heritage Holiday | Saturday, Dec. 9 + Saturday, Dec. 16 | 11 a.m.-3 p.m. | History Park | $5-$10 | Enjoy festive activities, seasonal treats, and crafts.

Christmas Book Reading & Hot Chocolate | Saturday, Dec. 16 | 12:30-1:30 p.m. | Jiaren Cafe | $30 | Author Aleena Thomas will read her first release, “The Magic of Christmas,” while the young ones enjoy a cup of hot cocoa.

Brunch with Santa | Sunday, Dec. 24 | 9 a.m.-1 p.m. | Hayes Mansion | $34.80-$54 | Little ones can decorate festive cookies, write letters + meet the big man himself.

Two adults decorate gingerbread houses.

Who doesn’t love decorating a gingerbread house?

Photo via History San José

Holiday happenings

Holiday Candlelight Tour | Saturdays through Saturday, Dec. 30 | Times vary | Winchester Mystery House | $19.99-$49.99 | See the mansion decked-out in holiday decor and uncover tales of Victorian traditions.

First Sunday Comedy Showcase | Sunday, Dec. 3 | 6-8 p.m. | Fox Tale Fermentation Project | Free | Kick off the holiday season with a lineup of Bay Area comedians, a free raffle, drinks, and good food.

Spirit of the Row | Tuesdays, Dec. 5, 12, and 19 | 6-8 p.m. | Santana Row Main Stage (across from Left Bank) | Free | Enjoy holiday performances from local community groups + hot cocoa to-go from Left Bank.

Viva Holidays: “Elf” | Friday, Dec. 8 | 6-9 p.m. | Lake Cunningham Cypress Pavilion | Free | Watch the classic holiday film starring Will Ferrell, enjoy seasonal activities, and experience a tree lighting.

408 Christmas Toy Drive | Saturday, Dec. 9 | 11 a.m.-4 p.m. | Independence High School | Free | 408 Ryders invite you to enjoy music, raffles, vendors, food, and more — an unwrapped toy or $20 cash donation is encouraged.

Laying Low for the Holidays | Saturday, Dec. 9 | 12-4 p.m. | 20 Barack Obama Blvd. | Free | In partnership with Creekside Socials, the SJ Lowrider Council will host a show + shine, toy drive, and book release of “ABC’s of Lowriding” by Ricardo Cortez.

Christmas Decoupage Workshop | Saturday, Dec. 9 | 4-6 p.m. | Jiaren Cafe | $40-$75 | Learn how to layer, paint, varnish, and seal to create a one-of-a-kind piece.

Winter Wonderland | Sunday, Dec. 10 | 10 a.m.-12 p.m. | Emma Prusch Farm Park | Free | Celebrate the holidays with Santa photos, lowriders, and hot chocolate + pan dulce.

Gingerbread House Making Get Together | Sunday, Dec. 10 | 4-6 p.m. | Taplands | Free | The brewery brings back its festive tradition with family-friendly fun, prizes + hot apple cider — bring your own kit.

Frosty Fest | Thursday, Dec. 14 | 4-8 p.m. | Santa Clara Convention Center | Free | Watch live gingerbread cookie decorating + enjoy performances from San Jose Ballet, Montage Dance, and more.

Pop-Up Games and Crafts | Saturday, Dec. 16 | 12-3 p.m. | Discovery Meadow | Free | Bring the whole family and enjoy games, ornament-making, and more.

12th Annual Santa Run SV | Sunday, Dec. 17 | 8 a.m. | Santa Clara + Market streets | $25-$50 | Run and walk alongside Santas, elves, reindeers, and more through downtown San Jose.

San Jose Park Ranger Holiday Campfire and Food Drive | Sunday, Dec. 17 | 3-5 p.m. | Kelley Park Amphitheater | Free | Gather ‘round the fire, eat s’mores, and help those in need.

Christmas Brunch | Monday, Dec. 25 | 11 a.m. | Signia by Hilton Hotel | $76.40-$145.85 | Indulge in seasonal favorites from an expansive Christmas buffet.

A gif of holiday lights in Blinky's Holiday Light Drive-Thru.

All of the lights...

Light displays

San Jose Brew Bike Holiday Tour | Select weekends through Sunday, Dec. 24 | Times vary | Goosetown Lounge, Willow Glen | $45-$450 | Take a 60-minute pedal tour through the lit-up streets of Willow Glen + feel free to bring snacks and non-alcoholic beverages — minors 13+ are welcome to join.

Cali Wagon Willow Glen Holiday Ride | Weekends through Sunday, Dec. 24 | Times vary | CVS parking lot on Lincoln Ave. | $24-$35 | Santa’s wagon takes you on a ride through one of San Jose’s most cherished traditions — Willow Glen’s neighborhood light displays.

Willow Glen Christmas Lights Pedicab Tours | Select weekends through Saturday, Dec. 23 | Times vary | Willow Glen Funeral Home Parking Lot | $33 | Eco City Cycles is offering open-air tours through one of the most decorated neighborhoods in town.

Fantasy of Lights Drive-Thru 2023 | Tuesday, Dec. 5-Saturday, Dec. 30 (excluding Christmas Day) | 6 p.m. | Vasona County Park | $30-$100 | A holiday tradition since 1999, experience larger-than-life light displays along a 1.5-mile road.

Trolley Ride Throughout Willow Glen | Thursday, Dec. 7-Sunday, Dec. 10 + Thursday, Dec. 14-Thursday, Dec. 21 | 5:15-9 p.m. | Bank of America parking lot, Willow Glen | $20-$40 | This 30-minute ride will take you through festive neighborhoods where you can see unique yard trees + fun decorations.

Goombahs Christmas Lights Cruise | Saturday, Dec. 16 | 5-7 p.m. | 1261 Lincoln Ave. | Free | This car show, toy drive, and cruise takes place in the bright neighborhood of Willow Glen.


Festive drinks, live music, and more await at the holiday bar pop-ups.

Photo via @nomikaisj

Adults only

Check out our guide to local holiday bar pop-ups.

Holiday Bubbly Walk | Saturday, Dec. 2 | 2-5 p.m. | Bank of America parking lot, Willow Glen | $60-$65 | Taste different wines at 20+ local Willow Glen businesses.

The Groove Before Christmas | Saturday, Dec. 9 | 8 p.m. | Continental Bar & Lounge | $10 | Dance the night away with resident DJs Hood Aliens, Mario Fitoria, Del Real, and all the way from Spain — DJ Kuff.

Heritage Holiday Adult Gingerbread House Decorating Workshop | Friday, Dec. 15 | 8-10 p.m. | Gonzalez/Peralta Adobe House | $35-$60 | Sip on cocktails while creating your own gingerbread abode.

The Official Christmas Bar Crawl | Saturday, Dec. 16 | 4 p.m. | Three Sisters Bar | $5-$20 | Drink your way through downtown at Fuze Bar & Grill, Splash, The Brit, Old Wagon Saloon & Grill, and Tiki Pete.

Let’s Get Lit Bingo Night | Wednesday, Dec. 20 | 7:30-9:30 p.m. | Britannia Arms Almaden | Free | Get elfed up and play four rounds of bingo with fun Christmas prizes and food + drink specials.

Someone dressed as the Grinch sits in a chair in front of the Santana Row Christmas Tree.

The Grinch has been frequenting San Jose hot spots this holiday season.

Holiday performances

See our guide to winter plays + concerts.

NYE celebrations

Persian 2024 New Year Party | Friday, Dec. 29-Saturday, Dec. 30 | 7 p.m. | Miami Beach Club | $45-$90 | This two-night party features DeeJay PS from Toronto with resident DJ Shotdown.

Noon Year’s Eve Celebration | Sunday, Dec. 31 | 9:30 a.m.-12:30 p.m. + 1:30 p.m.-4:30 p.m. | Children’s Discovery Museum | $16-$18 | Join the kiddos in counting down in different time zones with the museum’s version of a ball drop + lots of confetti.

Crawl ‘Til The Ball Falls | Sunday, Dec. 31 | 6 p.m. | O’Flaherty’s Irish Pub | $15-$45 | Get ready to celebrate the new year at The Brit, Dr. Funk, El Cabron Cantina, and more.

New Year’s Eve at Signia | Sunday, Dec. 31 | 8 p.m. | Signia by Hilton Hotel | $135 | Enjoy bites from Fountain, then head to AJI Bar & Robata to ring in the new year with a Veuve Clicquot toast + live music.

Happy New Year 2024 | Sunday, Dec. 31 | 9 p.m. | Studio M Ballroom Club | $25-$470 | This swanky affair features two levels of dance floors with DJs spinning Bollywood, hip-hop, Punjabi, Bhangra, Tollywood + South Indian tunes.

New Year’s Eve at Bay 101 Casino | Sunday, Dec. 31 | 9 p.m. | The Province | $40-$80 | With three rooms to roam and celebrate, enjoy tunes all night long from DJs Spindizzy and Encanto, plus a performance from the Groove Foundation Band.

New Year’s Eve Extravaganza VIII | Sunday, Dec. 31 | 8 p.m. | Downtown San Jose Marriott Hotel | $70-$950 | Count down to the new year with a free champagne toast + hors d’oeuvres, and tracks from DJs Brotha Reese, Chuy Gomez, and Mind Emotion.

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