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 just around the corner for the great 408.

Gather the family and friends and celebrate what makes the holiday season special with this guide featuring 46 winter events happening between December and January.

A Christmas in the Park display of bears ice skating.

Christmas in the Park always has interesting and festive displays.

🎁 Festivals and markets

Enchant | Now-Sunday, Jan. 1 | Times vary | PayPal Park, 1123 Coleman Ave., San Jose | $25+ | 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 | Now-Sunday, Jan. 1 | 12-10 p.m. | Plaza de Cesar Chavez, 1 Paseo de San Antonio, San Jose | Free entry | Explore this San Jose holiday tradition with the new Aloha Roller Rink addition.

Merchant Market | Friday, Dec. 2-Sunday, Dec. 4 | 12-6 p.m. | 1545 Parkmoor Ave., San Jose | Free entry | Enjoy live music, vendors, and good food from local eateries.

Menagerie Holiday Oddities & Curiosities Market | Saturday, Dec. 3-Sunday, Dec. 4 | 10 a.m.-5 p.m. | Winchester Mystery House, 525 S. Winchester Blvd., San Jose | Free with mansion tour ticket | Shop from a strange collection of collectibles, antiques, and handmade wares. 🔮

Culture Night Market X-Mas Series | Saturdays, Dec. 3, 10, and 17 | 3-9 p.m. | Oak Grove High School, 285 Blossom Hill Rd., San Jose | Free entry | Browse from more than 40 local vendors, and enjoy live entertainment and crafts for the kids.

Holiday Moment Market | Saturdays and Sundays, Dec. 3, 10, 11, and 18 | Times TBA | Moment SJ, 60 N. San Pedro St., San Jose | Free entry | Shop from featured weekly vendors every weekend in December. 🛍️

Fiesta Navideña Con Las Cafeteras | Friday, Dec. 9 | 5:30-9:30 p.m. | School of Arts and Culture at the Mexican Heritage Plaza, 1700 Alum Rock Ave., San Jose | Free | The family-friendly event includes a vendor market, Mexican cuisine, traditional folk music, and more.

Los Lagos Annual Holiday Open House | Saturday, Dec. 10 | 12-3 p.m. | 2995 Tuers Rd., San Jose | Free | Bring the family for pictures with Santa, horse-drawn carriage rides, crafts, and more.

Holiday Market | Sunday, Dec. 11 | 12-7 p.m. | Silicon Valley Sports, 2099 S. 10th St., Ste. 90, San Jose | Free entry | Silicon Valley Pop-Up presents its small business fair with more than 40 vendors, raffles, and a visit from Santa.

Creepmas | Sunday, Dec. 11 | 1-9 p.m. | 30 Post St., San Jose | Free entry | Head to a spooky holiday market full of local vendors. 👻

Holiday Artisan Market | Saturday, Dec. 17-Sunday, Dec. 18 | 10 a.m.-4 p.m. | Pruneyard Shopping Center, 1875 S. Bascom Ave., Campbell | Free entry | Shop unique gifts while enjoying live music.

Two dogs sitting in front of a Christmas in the Park display.

Everyone is getting into the holiday spirit.

Photo via @smooshy_mooshy

🎄 Holiday happenings

Movie Mondays | Now-Monday, Dec. 26 | 6 p.m. | Plaza de Cesar Chavez, 1 Paseo de San Antonio, San Jose | Free | Enjoy Christmas classics every Monday at Christmas in the Park.

Sippin’ Santa at 55 South | Now-Saturday, Dec. 31 | Times vary | 55 South, 55 S. First St., San Jose | Free entry | Sip on tropical, holiday-themed cocktails on select days of the week. 🍹

Holiday Bubbly Walk | Saturday, Dec. 3 | 2-5 p.m. | Downtown Willow Glen, Lincoln Ave., San Jose | $50+ | Sip, stroll, and shop.

A Christmas Party Fundraiser | Saturday, Dec. 3 | 4-11 p.m. | Britannia Arms Cupertino, 1087 S. De Anza Blvd., San Jose | Free entry | Adopt My Block presents this dog-friendly event featuring raffles, a silent auction, and food to raise money for its rescue efforts.

Winter Nights | Friday, Dec. 2-Saturday, Dec. 3 | 1-8 p.m. | Westfield Valley Fair, 2855 Stevens Creek Blvd., San Jose | Free | This event has fun for all ages with ornament engraving, a craft workshop, live music, and more.

Menorahs and Miracles | Sunday, Dec. 4 | 1:30-4:30 p.m. | Children’s Discovery Museum, 180 Woz Way, San Jose | $14+ | Make celebratory candles, go on a scavenger hunt, and enjoy a traditional Hanukkah treat. 🕯️

Merry Woofmas | Sunday, Dec. 4 | 12-4 p.m. | Moment SJ, 60 N. San Pedro St., San Jose | Free entry | Treat your furry friend to holiday goodies and snap a picture for your paw-liday card.

Holiday Gingerbread House Decorating | Fridays, Dec. 9 and 16 | 7:15-10 p.m. | History Park, 635 Phelan Ave., San Jose | $30+ | Channel your inner child while you enjoy wine, beer, and light snacks. 🍻

“Light in Dark Times” | Friday, Dec. 9 | 5:30-8 p.m. | Chopsticks Alley Art Gallery, 38 S. Second St., San Jose | Free | Create holiday ornaments for Chopsticks Alley Arts’ community tree, to be donated to Asian health organizations.

Breakfast with Santa | Saturday, Dec. 10 | Time TBA | Signia by Hilton, 170 S. Market St., San Jose | $50-65 | Grab a meal with the big guy. 🎅

Holiday Wreath Making | Saturday, Dec. 10 | 11 a.m.-5 p.m. | Splunk Plaza at Santana Row, 500 Santana Row, San Jose | $60 | Create a personalized wreath using locally sourced evergreen, dried florals, and more.

Christmas Sweater Dance Party | Saturday, Dec. 10 | 12-4 p.m. | Westfield Oakridge, 925 Blossom Hill Rd., San Jose | Free entry | Bust a move, sip hot chocolate, and win prizes.

Ainsley House Holiday Teas and Tours | Sunday, Dec. 11 | 12-2 p.m. | Ainsley House, 300 Grant St., Campbell | $60 | See the historic house decked out for the holidays while enjoying finger sandwiches and sparkling cider. 🫖

Menorah Lighting | Monday, Dec. 19 | 5:30-8 p.m. | Westfield Oakridge, 925 Blossom Hill Rd., San Jose | Free | Join Chabad of San Jose and celebrate Hanukkah with live music, food, and arts and crafts for the kids.

Let’s Get Lit Christmas Bingo Party | Wednesday, Dec. 21 | 7-9 p.m. | Britannia Arms Almaden, 5027 Almaden Expy., San Jose | Free | Enjoy food and drink specials, holiday prizes, and more.

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

All of the lights...

Light displays

Blinky’s Holiday Drive-Thru | Saturday, Nov. 26-Sunday, Jan. 1 | Times vary | Lake Cunningham Park, 2333 S. White Rd., San Jose | $30 per car | Watch an illuminated show from the comfort of your car. 🚗

Thornton Way Display | Saturday, Nov. 26-Sunday, Jan. 1 | Nightly until 10 p.m. | Thornton Way, Downing Ave., San Jose | Free | Catch the impressive, locally produced light extravaganza of more than 50,000 music-synchronized lights.

Kaybe Court Lights | Thursday, Dec. 1-Sunday, Jan. 1 | Times vary | 259 Kaybe Ct., San Jose | Free | Tune in to 99.5 FM and walk through Bobby and Genee Bimbi’s display of nearly 25,000 lights. 💡

Fantasy of Lights Drive-Thru | Tuesday, Dec. 6-Friday, Dec. 30 | Times vary | Vasona Lake County Park, 333 Blossom Hill Rd., Los Gatos | $5+ | See more than 50 light displays and a 90-foot twinkling tree. 🎄

Heritage Holiday Light Show | Friday, Dec. 9-Sunday, Dec. 11 and Friday, Dec. 16-Sunday, Dec. 18 | Times vary | History Park, 635 Phelan Ave., San Jose | $5+ | Enjoy light displays around the park while enjoying holiday music and themed food.

Willow Glen Christmas Lights Pedicab Tours | Friday, Dec. 9-Friday, Dec. 23 | 5:30-7:30 p.m. | 1039 Lincoln Ave., San Jose | $35 | Join Eco City Cycles for an open-air ride through the Willow Glen neighborhood.

Holiday Lights Ride | Saturday, Dec. 17 | 6:30-8:30 p.m. | Ortega Park, 636 Harrow Way, Sunnyvale | Free | Join the Silicon Valley Bicycle Coalition on a six-mile ride through colorful light displays. 🚲

🎭 Holiday performances

A Drag Queen Christmas | Saturday, Dec. 3 | 8 p.m. | Center for Performing Arts, 255 Almaden Blvd., San Jose | $35+ | All ages are welcome at this upbeat show.

You-Sing-It Messiah | Monday, Dec. 5 | 7:30-9 p.m. | California Theatre, 345 S. First St., San Jose | $25 | Join the San Jose Baroque Orchestra in singing the sounds of the season. 🎶

Spirit of the Row | Tuesdays, Dec. 6, 13, and 20 | 6-7 p.m. | Santana Row Park, 377 Santana Row, San Jose | Free entry | Catch guest performances by local groups and schools as they take on holiday productions.

12 Days of Christmas Cheer | Wednesdays, Dec. 7, 14, and 17 | 6:30-8 p.m. | Eastridge Mall, 2200 Eastridge Lp., San Jose | Free | Enjoy holiday performances by Lokahi Polynesian Dance Group, Eastside Youth Athletic Club, and local saxophonists.

The 57th Annual Nutcracker | Friday, Dec. 9-Sunday, Dec. 11 | Times vary | Center for Performing Arts, 255 Almaden Blvd., San Jose | $44+ | The San Jose Dance Theater returns for the Bay Area family tradition, running since 1964. 🩰

Carols in California | Saturday, Dec. 10 | 7-9 p.m. | California Theatre, 345 S. First St., San Jose | $26+ | Sing your favorite carols with Symphony San Jose.

Holiday Pops Concert: Festive Favorites | Sunday, Dec. 11 | 2:30-4 p.m. | California Theatre, 345 S. First St., San Jose | $15+ | The Golden State Youth Orchestra presents four ensembles to celebrate the holiday season. 🎼

🎆 NYE celebrations

Crawl ‘Til The Ball Falls | Saturday, Dec. 31-Sunday, Jan. 1 | 6 p.m.-2 a.m. | O’Flaherty’s Irish Pub, 25 N. San Pedro St., San Jose | $20+ | Enjoy this New Years Eve bar crawl full of drink specials. 🍸

Bollywood New Year Party | Saturday, Dec. 31-Sunday, Jan. 1 | 10:30 p.m.-1:30 a.m. | 418 S. Market St., San Jose | $30 | Close out the last night of 2022 with music brought to you by BollyTadka.

New Year’s Eve Extravaganza VI | Saturday, Dec. 31-Sunday, Jan. 1 | 8 p.m.-2 a.m. | Downtown San Jose Marriott Hotel, 301 S. Market St., San Jose | $60+ | Ring in the new year with free champagne, party favors, and hors d’oeuvres. 🍾

New Year’s Eve Party | Saturday, Dec. 31 | 7 p.m. | Holiday Inn San Jose, 1350 N. First St., San Jose | $80+ | Dance to hits from the 1960s and beyond with local band Tortilla Soup.

Rooftop New Year’s Eve Party | Saturday, Dec. 31-Sunday, Jan. 1 | 8 p.m.-12:30 a.m. | Silicon Valley Capital Club, 50 W. San Fernando St., San Jose | $265+ | Celebrate atop the city lights with late night bites, live music, a photo booth, and a midnight champagne toast. 🥂

8th Annual Black Tie NYE Event | Saturday, Dec. 31-Sunday, Jan. 1 | 8 p.m.-1:30 a.m. | SP2 Communal Bar + Restaurant, 72 N. Almaden Ave., San Jose | $20+ | Party with Heavy Arsenal and dance to R&B, house, and club classics.

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