Joyful & Triumphant

So many holiday to-dos and so little time—never fear! Gentry’s Holiday Guide features some of the Bay Area’s best holiday happenings.

Holiday Homes, Tours & Events

Enjoy a feast of festivities, from tea parties and parades to soirees and sing-alongs.

The Great Dickens Christmas Fair & Victorian Holiday Party

DECEMBER 1, 7, 8, 14, 15, 21, 22

A cherished Bay Area holiday tradition returns to the historic Cow Palace. Each holiday season, over three acres of exhibition halls are transformed into the delightfully lively world of Charles Dickens’ London. Cheerful calls of street vendors meld with songs of holiday carolers; enticing aromas of roasted chestnuts and hearty foods fill the air; and inviting shops overflow with one-of-a-kind Christmas gifts. The Dickens Christmas Fair is a treasured Bay Area tradition since 1970 and a splendid way to celebrate the holidays. 10 AM – 7 PM daily.

Cow Palace, Daly City
www.dickensfair.com


Holiday Teddy Bear Tea

DECEMBER 1, 7 – 9, 14 & 15, 20 – 23

An annual holiday tradition, children are invited to gather for Teddy Bear Tea in the festively decorated Terrace Room at The Ritz-Carlton, San Francisco. While children enjoy a special tea experience of hot chocolate, teddy bear cut-out cookies, and assorted sandwiches, they are entertained and engaged with a lively holiday show starring an entertaining elf, his animated sidekick, and a giant Teddy Bear. Each child will receive a teddy bear gift and photo with the giant Teddy Bear to take home. A portion of the proceeds will benefit Make-A-Wish Greater Bay Area.

The Ritz-Carlton, San Francisco
www.ritzcarlton.com


The Fairmont Gingerbread House & Holiday Tea

DECEMBER 1 – 31

Once again, Fairmont San Francisco’s elves are working overtime to create a dazzling, unparalleled winter display. The highlight of this awe-inspiring exhibit is the two-story giant Gingerbread House in the hotel’s grand lobby. Make the whole holiday excursion complete by reserving your spot at the hotel’s Gingerbread Holiday Tea. (Note: during the holiday’s busiest times, only overnight guests of the hotel are guaranteed access to the Gingerbread House and giant Christmas Tree in the lobby.)

Fairmont Hotel, 950 Mason Street, San Francisco
www.fairmont.com/san-francisco


Holiday Soiree to Benefit JW House

DECEMBER 5

Don’t miss the Santana Row Haute Holiday Soiree, a benefit for JW House, an organization that strives to keep families together during crisis. Enjoy wine tastings inside Santana Row shops, carolers, holiday sweet treats, hunky Santa photos, mistletoe-making, and much more.

Santana Row, San Jose
www.santanarow.com


Valle Monte League’s Christmas Tree Elegance

DECEMBER 6 – 7

One of Silicon Valley’s most beloved holiday traditions returns to San Jose. This two-day magical and modern fundraiser includes two Champagne Brunches and the Gratitude & Glitter Gala complete with spectacular designer trees and fashion shows.

Double Tree by Hilton, San Jose
www.vallemonte.org


Christmas at Our House

DECEMBER 6 – 7

Now in its 30th year, Christmas At Our House (CAOH) benefits Tuition Assistance programs for students at Saint Francis High School. Event highlights include a Gala Christmas Party, a Gift Boutique, and a Festive High Tea, along with entertainment showcasing Saint Francis family musicians and vocalists and a prize raffle.

Saint Francis High School, Mountain View
www.sfhs.com


The Twelve Days of Christmas

DECEMBER 6 – 7, 10 – 14 & 17 – 21

This December, Chef Christopher Kostow and The Restaurant at Meadowood team return for an all new The Twelve Days of Christmas. During this 12-day charitable celebration, influential chefs from around the world travel to The Restaurant at Meadowood to cook in collaboration with Chef Kostow, utilizing the products and inspiration of the Napa Valley. This year’s celebration will benefit Saint Helena Preschool for All, Inc., a local nonprofit organization providing scholarships to 3- and 4-year-old children. In the spirit of the Holiday Season, guests are encouraged to bring an unwrapped toy to each event, which will then be distributed throughout the Napa Valley.

The Restaurant at Meadowood, Napa
www.therestaurantatmeadowood.com


Children’s Holiday Parade

DECEMBER 7

Now in its 63rd year, this community event is sponsored by the Los Gatos Lions Club and LGS Recreation, in cooperation with the Town of Los Gatos and Los Gatos High School. Regardless of weather, the parade starts promptly at 11 AM, rain or shine. Be sure to check the LGS Recreation website, which will host a variety of festivities throughout the season, including breakfast with Santa, holiday sing-along, keepsake ornament decorating, and a holiday arts and crafts fair.

Parade begins at Almendra Avenue at North Santa Cruz Avenue, Los Gatos


Holiday Heroes

DECEMBER 10

Join Wender Weis Foundation for Children and be amazed as the Club Level at Oracle Park, home of the San Francisco Giants (2010, 2012, and 2014 World Series Champions), transforms into a holiday wonderland for families and children. Watch wonder spark as over 500 underserved youth connect with their favorite professional athletes. Holiday Heroes endeavors to connect at-risk children with professional athletes with the goal of providing the recipient children with hope and direction.

Oracle Park, San Francisco
www.holidayheroes.org


Holidays at Filoli

Holidays at Filoli

THROUGH DECEMBER 30 

Filoli has never been more festive with its new Holiday tradition, wherein the House will feature a fresh take on seasonal décor in every room and the elegantly lit Gardens will remain open late. Indulge in Holiday Tea with a traditional tiered tray served at each table with delicious finger sandwiches, freshly made scones, and delicate holiday treats, served alongside clotted cream and Filoli Clock Tower Shop jam. Shop at the Clock Tower Shop and enjoy live entertainment and refreshments at the Quail’s Nest Café. During two Artisan Market weekends, a large selection of local vendors will sell handmade goodies and gifts (open 11 AM – 7 PM on November 23 and 24, as well as November 29, 30, and December 1.)

Filoli, Woodside
www.filoli.org


33rd Annual Holiday Windows at Macy’s Union Square

THROUGH JANUARY 1

Window-shopping doesn’t get any better than Macy’s Union Square Holiday Windows filled with adoptable animals from the San Francisco SPCA and, for the first time ever, San Francisco Animal Care and Control. Last year alone, 239 animals found new homes in time for the holidays, and more than $77,000 was raised to support the SF SPCA’s lifesaving programs. In addition to cats and dogs, this year’s Holiday Windows will feature adorable, adoptable small animals like rabbits, chinchillas, and guinea pigs. The SF SPCA and SF ACC are also hosting two special Cuddle Experiences, where visitors can snuggle with adoptable animals. $10 gets 10 minutes of snuggles!

Macy’s Union Square, San Francisco
www.sfspca.org


 


Here Comes Santa Claus!

Old Saint Nick is ready to meet children of all ages at these very merry venues near you.

Breakfast with Santa

DECEMBER 7

Santa will arrive at the Arrillaga Family Recreation Center in Menlo Park for a delicious pancake breakfast and festive children’s crafts co-sponsored by the Menlo Park Rotary Club and the City of Menlo Park Community Services Department. Be sure to make a reservation, as the multiple seatings fill up quickly. ($10 for adults and $8 for children under 12.) Donate an unwrapped toy for the Firefighter Toy Drive and receive $1.00 of the ticket price. The fun runs from 7:30 – 11:30 AM.

Arrillaga Family Recreation Center
www.menlopark.org


Hometown Holidays and Children’s Parade

DECEMBER 7

Enjoy Redwood City’s best holiday shopping, play in the snow, take a photo with Santa, join festivities inside the San Mateo County History Museum (open, free admission), enjoy special musical performances, and more. Top off the evening by watching the Tree Lighting Ceremony in Courthouse Square. It’s all happening on Saturday, December 7 at 10 AM, RAIN or SHINE!

Downtown Redwood City
www.hometownholidays.org


Santa Paws

DECEMBER 8

Santa adores pet lovers big and small. Bring your favorite furry canine or feline friend to Santana Row for a photo with Santa. All proceeds will benefit the Humane Society Silicon Valley. (Photos are $25.) “Furry up” and be there 11 AM – 3 PM.

Park Valencia at Santana Row, San Jose
www.santanarow.com


Napa Valley Santa Train

Napa Valley Santa Train

THROUGH DECEMBER 27

Treat the little ones to a truly magical, musical, and memorable family Christmas adventure. This year holiday elves have transformed the Wine Train into an enchanting holiday experience. Climb aboard with Santa, Jolly the Bear, and their holiday friends to embark on a special Christmas mission and experience you won’t get anywhere else. Play games and join in sing-a-longs with a fun cast of characters on your way to Santa’s village and workshop. Sip hot cocoa and munch on freshly baked cookies. (Train fares for the Santa Train start at $59.99 per person Monday – Thursday and $79.99 per person Friday and Saturday.)

Napa Valley Wine Train, Napa
www.winetrain.com


Magically, Santa also appears around the Bay…

  • Bay Area Discovery Museum, Sausalito
  • Hillsdale Shopping Center, San Mateo
  • Los Gatos Town Plaza, Los Gatos
  • Macy’s Union Square, San Francisco
  • Stanford Shopping Center, Palo Alto
  • San Francisco Zoo, San Francisco
  • Santana Row, San Jose
  • Westfield San Francisco Centre, San Francisco
  • Westfield Valley Fair, Santa Clara

 


‘Nutcracker, I do love you!’

A bevy of Nutcracker performances abound throughout the Bay Area this month. As always, Tchaikovsky’s beautiful music is guaranteed holiday season magic.

It’s a Wonderful Nutcracker

DECEMBER 13 – 15 & 21 – 22

This exciting work from Menlowe Ballet’s Artistic Director Michael Lowe is one of the hottest new Bay Area holiday traditions. It’s a Wonderful Nutcracker blends the magic and wonder of a traditional Nutcracker with the heartwarming message from Frank Capra’s 1940s film, It’s a Wonderful Life, and brings two of the world’s most heralded holiday classics together on one stage

Menlo Atherton Performing Arts Center, Atherton
www.menloweballet.org


Santa Clara Ballet’s The Nutcracker

DECEMBER 14 – 15

Celebrating its 46th anniversary, the Santa Clara troupe presents a family friendly, full-length, traditional version of this classic holiday story. This delightful classic spotlights acclaimed dance professionals alongside company soloists and pre-professional students from schools and dance companies throughout the San Francisco Bay Area.

Santa Clara Convention Center
www.santaclaraballet.com


Los Gatos Ballet’s The Nutcracker

DECEMBER 20 – 22

Join Clara on her adventures as she travels to magical realms with suspenseful battles, beautiful palaces, and delightful sweets. Let the superb dancing and Tchaikovsky’s iconic score captivate you and your family this Holiday season.

McAfee Center for Performing Arts, Saratoga
www.losgatosballet.org


San Francisco Ballet’s Nutcracker

DECEMBER 11 – 29

San Francisco Ballet (SF Ballet) presents the 75th anniversary of America’s first full-length Nutcracker with a myriad of events and giveaways this holiday season, culminating in performances of Artistic Director and Principal Choreographer Helgi Tomasson’s set-in-San Francisco Nutcracker, danced to Tchaikovsky’s timeless score.

War Memorial Opera House, San Francisco
www.sfballet.org


Peninsula Ballet’s Nutcracker

DECEMBER 21 – 22 & 27-28

Gregory Amato’s exuberant reimagining of The Nutcracker reinvigorates this beloved holiday tradition with a 21st-century sensibility, while cherishing all of our favorite Nutcracker moments. The Stahlbaum children and a cast of delightful characters leap from the pages of Drosselmeyer’s book to weave an uplifting tale filled with compassion, playfulness, and triumph—with a sprinkling of pure holiday magic from the Fairy of Inspiration.

Fox Theatre, Redwood City
www.peninsulaballet.org


Moscow Ballet’s Great Russian Nutcracker

NOVEMBER 5

This Christmas, give your family the gift of Moscow Ballet’s Great Russian Nutcracker. Step into a simpler time filled with sweet dreams and Christmas magic. With world-class artists, over 200 dazzling costumes, stunning sets, towering puppets, and soaring birds, don’t miss your chance to ring in the holidays with this acclaimed Christmas extravaganza.

Palace of Fine Arts Theatre, San Francisco
www.palaceoffinearts.org


 


Ooooh Baby, It’s Cold Outside

Bundle up and go for a spin on the Bay Area’s best ice.

Holiday Ice Rink at Embarcadero Center

THROUGH JANUARY 5

Celebrate the Holiday Spirit in San Francisco at the Bay Area’s largest outdoor ice rink, a beautiful city setting, and an array of shops and restaurants to enjoy. This is signature San Francisco and it’s what makes The Holiday Ice Rink at Embarcadero Center, presented by Hawaiian Airlines, the perfect place for holiday fun. (General admission $12. $7 children under 7.)

Justin Herman Plaza at Embarcadero Center, San Francisco
www.embarcaderocenter.com


Safeway Holiday Ice Rink at Union Square

Safeway Holiday Ice Rink at Union Square

THROUGH JANUARY 20

Lace up your skates at The Safeway Holiday Ice Rink in Union Square presented by Alaska Airlines. Everyone can enjoy ice-skating in San Francisco’s iconic plaza surrounded by the sights and sounds of the season.

Union Square, San Francisco
www.unionsquareicerink.com


San Mateo on Ice

THROUGH JANUARY 6

Glide into the holidays and ice-skate through San Mateo’s Central Park. The San Mateo on Ice Holiday Rink offers the quintessential winter activity right near downtown. Don’t miss the chance to try bumper cars on ice. It’s the only place in California where you can!

Central Park, San Mateo
www.onicerinks.com


Kristi Yamaguchi Downtown Ice

THROUGH JANUARY 15

Kristi Yamaguchi has been part of Downtown Ice for nine seasons. Since moving to the Circle of Palms, Downtown Ice has attracted 592,000 skaters and more than 1 million visitors. It is the only rink in the world that offers skating in and around a circle of 32 palm trees. ($18 for adults. $15 for kinds under 10, military and seniors)

120 Market Street, San Jose
www.downtownicesj.com


Winter Ice Rink Downtown Sunnyvale

THROUGH JANUARY 20

Bring your family and friends and start a new holiday tradition. The Winter Ice Rink will kick off its inaugural season with an Opening Ceremony that’s not to be missed.

Winter Ice Rink, Downtown Sunnyvale
www.citylinesunnyvale.com


Winter Lodge

THROUGHOUT WINTER

There’s something truly magical about ice-skating out in the fresh air, and Palo Alto’s Winter Lodge is the only permanent outdoor ice rink west of the Sierras. A popular Peninsula tradition for 60 years now, Winter Lodge and its renowned skating school are open September 19 – April 11, 2020. ($11 single admission, $5 skate rental.)

Winter Lodge, Palo Alto
www.winterlodge.com


Nazareth Ice Oasis

THROUGHOUT WINTER

This classic indoor rink offers public skate sessions, hockey leagues, figure skating, and broomball for private parties.

3140 Bay Road, Redwood City
www.iceoasis.com


 


More Magical Performances
of the Season

Whether keeping steadfast to an annual family tradition or starting a new one, these must-see performances will put you and yours in a jolly holiday spirit.

A.C.T.’s A Christmas Carol

DECEMBER 1-24

Now in the theater’s 43rd year of presenting the holiday classic, the American Conservatory Theater’s version of A Christmas Carol—adapted by Paul Walsh and Carey Perloff—stays true to the heart of Dickens’ timeless story of redemption and brings a playful sensibility to his rich language.

A.C.T.’s Geary Theater, San Francisco
www.act-sf.org


Holiday Films with San Francisco Symphony

DECEMBER 3, 6, 17

Take the whole family to enjoy the outstanding sounds of the SF Symphony together with memorable holiday classics on the big screen! It’s a Wonderful Life and Love Actually have never sounded better.

Davies Symphony Hall, San Francisco
www.sfsymphony.org


Scrooge in Love

42nd Street Moon’s Scrooge in Love

DECEMBER 4-22

Ever curious what happened AFTER A Christmas Carol? Find out in this hilarious and heartwarming new holiday classic! Ebenezer Scrooge is out to find his lost love Belle, revisiting past, present, and future with ghostly friends old and new! 42nd Street Moon celebrates and preserves the art and spirit of the American Musical Theatre by presenting intimately produced performances of classic and rarely performed musical works.

Gateway Theatre, San Francisco
www.42ndstmoon.org


Transcendence’s Broadway Holiday Spectacular

DECEMBER 6 – 8

Join Transcendence Theatre Company, the award-winning creators of “Broadway Under the Stars,” for this new and reimagined holiday celebration for all ages, with an eclectic mix of Broadway showstoppers, holiday favorites, and modern twists on some of the world’s most uplifting and cherished songs.

Luther Burbank Center for the Arts, Santa Rosa
www.BestNightEver.org


The Velveteen Rabbit

THROUGH DECEMBER 8

For the 33rd season, the Oberlin Dance Company brings a beloved Bay Area holiday tradition to the stage in Margery Williams’ classic tale of a well-worn nursery rabbit that becomes “real.” Told through music, dance, and a powerful narrative, The Velveteen Rabbit celebrates the unique relationship between a little boy and his stuffed rabbit, and the enduring power of love.

The Blue Shield of California Theater at YBCA
www.odcdance.org


You-Sing-It Messiah

DECEMBER 9

Make your holiday voice heard at the You-Sing-It Messiah with the San Jose Symphonic Choir, an annual tradition for nearly 40 years. Under the direction of Music Director Leroy Kromm, the entire audience will participate in singing the beautiful solos and choruses of Handel’s beloved work, accompanied by the San Jose Baroque Orchestra.

California Theatre, San Jose
www.sanjosetheaters.org


A Chanticleer Christmas

A Chanticleer Christmas

DECEMBER 11

San Francisco’s own men’s choir, famous world-wide, brings its annual holiday celebration blend to Memorial Church. Since its 1978 founding in San Francisco by Louis Botto, Chanticleer has toured the world, winning bravos from the capitals of Europe to the greenways of Central Park, where the group has sung alongside the New York Philharmonic. It wouldn’t be December at Stanford without it.

Memorial Church, Palo Alto
www.live.stanford.edu


Smuin Contemporary Ballet’s The Christmas Ballet 

DECEMBER 12-23

With a stunning and original array of dance including ballet, tap, and jazz, The Christmas Ballet is set to holiday tunes, with the surprise unwrapping of new treats every year. The first act, Classical Christmas, features dancers in brilliant snow-white ensembles performing time-honored favorites of the holiday season. The Cool Christmas second act delivers a red-hot costume change along with a medley of modern and festive numbers.

Yerba Buena Center for the Arts, San Francisco
www.smuinballet.org


Carols in the California

DECEMBER 14

Artistic Director Elena Sharkova and the Symphony Silicon Valley Chorale, along with musicians of Symphony Silicon Valley, present the 15th-annual Carols in the California. This year’s program includes Broadway star Lisa Vroman joining the Chorale, singing a variety of holiday classics, all in the warm glow of the California Theatre.

California Theater, San Jose
www.symphonysiliconvalley.org


 


Deck the Halls

Save your precious holiday season hours and let these local decorating gurus spread holiday cheer throughout your home!


 


Celebrating Hanukkah

This year Hanukkah is observed from sunset on December 22 to nightfall on December 30, 2019.

Hanukkah Candle Lighting

DECEMBER 22 – 30

Illuminate the darkness and join in the lighting of the hanukkiah. Celebrate with stories about the holiday and sing along to music played by Jonathan Bayer. Savor festive fried treats and revel in one of the most beloved holidays of the Jewish year. The central tradition of candle lighting recalls a pivotal moment in Jewish history, when a little flame could light up a dark world.

JCC San Francisco
www.jccsf.org


Hanukkah Is Coming to Stanford Shopping Center

DECEMBER 29

Celebrate the Jewish festival of lights with a musical performance by the fabulous Noa Levy and her band, who will lead the audience in dancing both in English and Hebrew. Enjoy arts and crafts for the kids, dreidel games, and a special candle-lighting ceremony.

Stanford Shopping Center, The Plaza (near Neiman Marcus)
www.paloaltojcc.org


Glowing Hanukkah Party at Ghirardelli Square

DECEMBER 22

Celebrate the first night of Hanukkah by dressing up in your favorite light-up, glittery, and glowing clothes. Light candles, enjoy live music, make crafts, play games, and eat tasty treats. Hosted by the Jewish Community Center of San Francisco. (3 PM – 6 PM)

Ghirardelli Square, San Francisco
www.ghirardellisq.com


10th Annual Chanukah Festival

DECEMBER 22

Join Chabad MidPen for the 10th-annual Chanukah Festival and experience Chanukah in virtual reality! Live music, Chanukah gelt drop, latkes and donuts, arts and crafts, and plenty of fun for the whole family.

Courthouse Square, Downtown Redwood City
www.redwoodcity.org


 


Light Up Your Life

Need a little something extra to make the season magical? Let these expert lighting specialists help make your home extra merry and bright!


 


It’s Celebration Time—Happy New Year!

Ring in the ’20s in style with these hip and happening New Year kick-off events.

New Year’s Eve with Seth MacFarlane and the San Francisco Symphony

DECEMBER 31

Celebrate in style with Grammy Award-nominated singer, actor, and director Seth MacFarlane, who brings a winning combination of rich crooning and cool pizazz as he lights up the stage with the SF Symphony in a performance of jazz standards and holiday favorites conducted by Edwin Outwater.

Davies Symphony Hall, San Francisco
www.sfsymphony.org


Midnight Fireworks Over the Waterfront

DECEMBER 31

Every year the city of San Francisco puts on a spectacular fireworks show. Bundle up and enjoy the free 15-minute show, as brilliant fireworks synced to music are launched starting at 11:59PM near Pier 14. If you’re looking to get the best view of the fireworks, you’ll want to head for the cruises, hotels, and restaurants along the Embarcadero waterfront.

The Waterfront, San Francisco
www.sftravel.com

 

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