San Jose Playhouse – A Holly Jolly Holiday

3Below Theaters 288 S 2nd St, San Jose

San Jose Playhouse presents “A Holly Jolly Holiday!” at 3Below Theaters! Join them for a series of film and live events – FREE as well as ticketed – all designed to delight even the biggest Scrooge! If you’re looking for something to do this holiday season – for youth, families, and adults – then mark...

Downtown Ice

Circle of Palms 127 S Market St, San Jose

Kristi Yamaguchi's Downtown Ice in San Jose presented by First Tech Federal Credit Union and Alaska Airlines returns this holiday season! Come skate in the Circle of Palms under the twinkling lights. A portion of the proceeds from ticket sales will benefit Kristi Yamaguchi’s Always Dream, which serves underserved children and their families with early...


Christmas in the Park

Plaza de Cesar Chavez 1 Paseo de San Antonio, San Jose

Christmas in the Park is an annual holiday tradition that takes place in the heart of Downtown San José at the Plaza de Cesar Chavez. For over 40 years, this whimsical, lit-up event has brought people from all over the Bay Area together during the holidays.

Free Holiday Story Walk

3Below Theaters 288 S 2nd St, San Jose

Enjoy 3Below's lovingly created art installation featuring big, bright beautiful banners while you listen to favorite holiday stories, holiday songs, holiday humor, and holiday trivia…all presented as audio accompaniment in English, Spanish, and Vietnamese. This FREE walk-by experience is installed on San Carlos between 2nd and 3rd Streets and is open: November 27-December 19, 2021...

San Jose Playhouse – Live Music & Holiday Song Sing-Alongs!

3Below Theaters 288 S 2nd St, San Jose

San Jose Playhouse & 3Below are bringing the entertainment outdoors this holiday season so grab a cozy blankie, mittens, and earmuffs as we gather on their patio for live entertainment, holiday music, and fun! Their talented musicians will delight you with holiday tunes played on a variety of instruments to celebrate the season. Then, their...

San Jose Playhouse – Holiday Films From Santa’s Naughty & Nice List!

3Below Theaters 288 S 2nd St, San Jose

San Jose Playhouse curated a collection of the best holiday films. Catch these classics on the big screen with big sound while you enjoy delights from 3Below Cafe including peppermint hot chocolate and holiday popcorn!

A Drag Queen Christmas – The Naughty Tour

Center for the Performing Arts 255 S Almaden Blvd, San Jose

A Drag Queen Christmas is a magical (and hilarious) evening of holiday performances featuring contestants from the reality television show. Scheduled to Appear*: Trinity The Tuck, Monet X Change, Brooke Lynn Hytes, Kylie Sonique Love, Crystal Methyd, Heidi N Closet, Jan Sport and Alyssa Edwards. *Lineup is subject to change.

$35 – $150

White Christmas – CMT Marquee

Montgomery Theater 271 South Market St, San JOse

Veterans Bob Wallace and Phil Davis have a successful song-and-dance act after World War II. With romance in mind, the two follow a duo of beautiful singing sisters en route to their Christmas show at a Vermont lodge, which just happens to be owned by Bob and Phil’s former army commander. With a dazzling score...


San Jose Playhouse – Holly Jolly Holiday Experience

3Below Theaters 288 S 2nd St, San Jose

Kids of all ages will enjoy San Jose Playhouse's Holly Jolly Holiday Experience which includes food, fun, and film! $15 Admission Includes: A rotation to the 3 Imagination Stations where you can decorate a holiday photo frame, create a reindeer ornament, and write your letter to Santa Photos with adorably costumed holiday characters! Get your...


Toys for Tots “Stuff the Bus”

Plaza de Cesar Chavez 1 Paseo de San Antonio, San Jose

Join Christmas in the Park's annual Toys for Tots "Stuff the Bus" event with the US Marine Reserves and VTA. Come out and donate a new, unwrapped toy to help them fill a bus with toys! They will have a drive-thru lane set up on the Market Street Northbound side of the park.

City Lights Theater Company – Lights & Music: Ren’s 7th Annual Winter Wonderland

City Lights Theater Company 529 S 2nd St, San Jose

Enjoy some holiday favorites and new classics to kick off the most wonderful time of the year with the 7th Annual Ren's Winter Wonderland Concert, starring jazz, blues and country singer-songwriter Ren Geisick. After a successful virtual version of "Ren's Winter Wonderland'' in 2020, Ren is excited to be live, in person, and with the...


Hammer Theatre – San Jose State University Jazz Orchestra presents Cool Yule 2021

Hammer Theatre Center 101 Paseo De San Antonio, San Jose

Downtown San Jose will be extra chill this holiday season when the San Jose State University Jazz Orchestra returns to Hammer Theatre Center with Cool Yule, a jazz concert featuring the festive and familiar sounds of favorite holiday songs. The evening will begin with a special guest performance by Valley Christian High School Jazz Ensemble,...