Peninsula Cities Ring in Holiday Season With Activities Throughout December

Thousands poured into the Half Moon Bay historic district for the annual "Night of Lights" celebration to kick off a weekend of festivities in cities on the Peninsula. 

With the Caltrain Holiday Train making stops in four cities across San Mateo County throughout the weekend and a citywide gathering in Redwood City for "Hometown Holidays,” the weekend was full of family-friendly events, featuring everything from holiday carolers to artificial snow pits.

Here are more upcoming events and seasonal traditions to look for on the Peninsula in the next two weeks:

Caroling - Many holiday groups will be performing throughout the Peninsula this month. One of the holiday performances is by Golden Chordsmen, a barber shop quartet, on Dec. 9 at 7 p.m. in San Mateo Hillsdale Mall. The following day, Transfiguration Episcopal Church is hosting caroling from 2 to 4 p.m. at 3900 Alameda de las Pulgas, San Mateo. Men’s acappella group, Ragazzi Continuo, will be performing "Christmas Time Is Here" and other Christmas carols at St. Peter’s Episcopal Church, 178 Clinton St., Redwood City, on Dec. 10 at 7:30 p.m. Tickets are $15 to $20 in advance or $15 to $25 at the door. Burlingame Music Club will be performing on Dec. 12 at 1 p.m. at 241 Park Road, Burlingame, and the Gryphon Carollers will be performing its holiday concert on Dec. 17 at 7:00 p.m. at Cañada College Theater, 4200 Farm Hill Blvd, Redwood City.

Every Christmas Story Ever Told - In Half Moon Bay, actors are taking a different approach to the classic Christmas stories - by just telling them all. This local theatre is performing its show from Dec. 9 to 18 and tickets cost between $17 and $30. More information can be found on Coastal Repertory Theatre's website.

Holiday Festival - San Mateo High School Gym is hosting a “Holiday Festival of Dance" on Dec. 10 and 11 at 5:30 p.m. at 506 N. Deleware St., San Mateo. Tickets cost $2 for young children and $13 at the door for ages 13 and older.

Great Dickens Christmas Fair - This fair has been held in the Bay Area since 1970 and transforms a hall in Daly City into "Charles Dickens' London Town,” including everything from old fashioned shops to actors recreating scenes from history. The holiday party occurs between Nov. 19 and Dec. 18 from 10 a.m. to 7 p.m. with tickets costing between $14 and $30. Children aged five to 12-years old are admitted for free. The fair takes place at Cow Palace Exhibition Halls, 2600 Geneva Ave., Daly City. More information can be found on the Great Dickens’ website or at (800) 510-1558.

Hanukkah - Latkepalooza! is a free Hanukkah celebration on Dec. 11 from 1 to 3:30 p.m. at the Peninsula Jewish Community Center, 800 Foster City Blvd., Foster City. The Shamati Acoustic Trio will be performing, and there will be vendors for holiday shopping and wine tasting. More information can be found on the event's website.

Hillsdale Shopping Center Community Performances - In the middle of San Mateo County sits Hillsdale Shopping Center, which will be hosting local music groups and schools in its Nordstrom Court throughout the month. The performances are free and details on which holiday community performances will be there during your trip can be found on its website.

Holiday Market - The Half Moon Bay Ritz-Carlton is hosting a holiday market on its Ocean Lawn for the first time. The event is free with optional valet parking for $30. It will be held on Dec. 18 from noon to 5 p.m.

Ice Skating Holiday Rinks - With the newest outdoor ice skating rink, San Mateo on Ice, open for the season in San Mateo Central Park, 50 E 5th Ave, San Mateo, CA 94401, ice skating activities are in full swing for families on the Peninsula. Golden Gate Skating Rink, 1303 Main St, Redwood City, CA 94063, Winter Lodge, 3009 Middlefield Rd, Palo Alto, CA 94306, Nazareth Ice Oasis, 3140 Bay Rd, Redwood City, are among other ice skating locations in the area.

Holiday Concerts- Kitka women's chorus group will be arriving on the Peninsula for a "Wintersongs" performance at St. Bede’s Episcopal Church, 2650 Sand Hill Road, Menlo Park, on Dec. 11 at 4 pm. Tickets cost between $15 and $40. Tickets and more details can be found on its site. The Westbay Community Band will be performing its Winter Holiday Concert. on Dec. 14 at 7 p.m. at 400 Murchison Drive, Millbrae. Tickets are $10 at the door. Also on Dec. 14, Off the Grid will be hosting Groovy Judy for holiday songs at its food market from 6 to 7:30 p.m. at 1120 Merrill St. Menlo Park. The performance is free.

Mary Poppins - Hillbarn Theatre Company will be presenting the Disney classic from Nov. 25 to Dec. 18 at Hillbarn Theatre, 1285 E Hillsdale Blvd, Foster City. Tickets cost between $45 and $48. Tickets and more details can be found on its site.

Meeting Santa - Santa and his elves will be making their rounds throughout cities on the Peninsula all month. He will be joining San Mateo County librarians in San Carlos, 610 Elm St. San Carlos, on Dec. 17 from 12:30 to 1:30 pm and at the Hillsdale and Stanford shopping centers throughout the month. For a $10 donation or unwrapped new gift, families can join firefighters at Station 21, 120 S. Ellsworth Ave. San Mateo, for Breakfast with Santa on Dec. 10 from 9 to 11 a.m. Photos by Carl Ward Photography will be available for children meeting with Santa on the 1921 fire engine.

Nativity Scene - In Redwood City, Bethlehem A.D. performs their annual nativity scene for families on the Peninsula. Performances will occur from Dec. 21 to 23 from 6 to 9 p.m. at 1305 Middlefield Rd. Redwood City. 

The Nutcracker - In several cities, the Nutcracker will be performed in theatres throughout the Bay Area. On the Peninsula, some performances include Bay Pointe Ballet in San Mateo from Dec. 16 to 18 and at the Peninsula Ballet Theater in Redwood City on Dec. 17 and 18. Prices vary by performance. 

Our Lady of Guadalupe Pilgrimage - Every year, thousands embark on a 12-mile hike from All Souls Church, 315 Walnut Avenue, South San Francisco, to St. Mary’s Cathedral, 111 Gough Street San Francisco. This year, the journey will begin at 5 a.m. on Dec. 10 and end with a 2 p.m. mass on the steps of St. Mary’s Cathedral. More information can be found on Cruzada Guadalupana's website.

Pillar Point Harbor Lighted Boat Festival - The 29th annual festival in Half Moon Bay will be held on Dec. 10 from 6 to 8 p.m. There will be a boat decorating contest and vendors along the Pillar Point Harbor.

Tree Lighting Ceremonies -  The Foster City Recreation Center in Leo Ryan Park is hosting its annual tree lighting ceremony. It is free to attend on Dec. 7 from 5:30 to 7:30 p.m.

‘Twas the Night Before Christmas - More than 80 actors will put on the classic holiday performance on Dec. 10 and 11 with performances at 1 and 4 p.m. It will take place at Woodside Performing Arts Center, 199 Churchill Ave., Woodside. Tickets cost $15 for children and seniors and $25 for adults

Wine Stroll- San Carlos Chamber is hosting a holiday wine stroll in downtown San Carlos on Dec. 11 from 1 to 5 p.m. at the Cherry Street at Laurel, San Carlos for $40 per person (aged 21 and up). San Carlos will also be the site of a holiday mixer at Sparky's Hot Rod Garage from 5 to 7 p.m. on Dec. 14.

Wreaths Across America - A family-friendly tradition that supports our veterans, Wreaths Across America is looking for volunteers to assist in laying wreaths on Dec. 17 for a national moment of silence. The ceremony will start at 8:45 a.m. at Golden Gate National Ceremony, 1300 Sneath Lane, San Bruno. 

Do you know of another event happening on the Peninsula this month? Help us update this list by emailing

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