San Carlos and San Mateo County Holiday Events 2025

San Mateo County Winter 2025 Holiday Events

The holiday season in San Carlos and across San Mateo County turns the Mid-Peninsula into a festive destination full of community celebrations, outdoor markets, and family traditions. Here's your complete guide to the best holiday events happening this November and December.

What Holiday Events Are Happening in San Carlos This Season?

Harringtunes Fall Concerts

Kick off the season with live music at Frank D. Harrington Park on Laurel Street.

Schedule:

November 6: Rock the Voice (5:00-7:00 PM)
November 20: 19th Avenue Roadwork (5:00-7:00 PM)

The concerts feature local performers and permanent chess boards stocked with pieces. Grab dinner from downtown San Carlos restaurants and enjoy a relaxed evening of music. For those exploring neighborhoods in San Carlos, this downtown scene shows what life looks like in this close-knit community.

Details: https://cityofsancarlos.org/business_detail_T10_R152.php

Centennial Wrapped Community Movie Night

Burton Park hosts an outdoor movie night celebrating San Carlos history.

When: Saturday, November 15, 2025 (6:00-8:00 PM)
Where: Burton Park, 900 Chestnut Street
What to bring: Chairs, blankets, and warm clothes

The evening starts with a historical documentary, followed by community highlights from the past year. Light snacks and refreshments provided.

Details: https://www.cityofsancarlos.org/news_detail_T11_R532.php

15th Annual Night of Holiday Lights

This is the big one. Downtown San Carlos transforms into a holiday wonderland on Laurel Street, from San Carlos Avenue to Cherry Street.

When: Friday, December 5, 2025 (5:00-8:30 PM)
Where: Laurel Street, with the main stage on Cherry Street
Cost: Free

What to expect:

Family activities and arts and crafts
Beer and wine sales
Hot chocolate and holiday treats
Live musical performances
Festive lights and snow

Details: https://cityofsancarlos.org/business_detail_T10_R36.php

Christmas Tree Lane

Three blocks of decorated homes on Eucalyptus Avenue light up all December long.

When: All December until December 26th
Where: Eucalyptus Avenue, San Carlos, CA 94070

Some homes sell hot cocoa while you stroll the one-way pedestrian route. The street gets incredibly crowded, so park a few blocks away on streets like Arroyo and walk in. The city implements traffic control to manage the crowds.

Details:

As top San Carlos real estate agents, we know buyers love seeing these neighborhood traditions before making a decision.

Where Can Families Find Holiday Activities in Redwood City and Belmont?

Zoppé Italian Family Circus

This 18th-year tradition runs all November in an intimate 500-seat tent.

When: November 1-30, 2025 (matinee and evening performances)
Where: Main Library Parking Lot, 1044 Middlefield Road, Redwood City

The two-hour show features Nino the Clown, acrobats, trapeze artists, and equestrian performances that honor Old-World Italian circus tradition. Ringmaster Patrick McGuire leads audience participation throughout.

Details: https://www.redwoodcity.org/residents/redwood-city-events/zoppe-italian-family-circus

ART on the Square's 10th Anniversary Holiday Show

Shop from over 25 local artists under the stained glass dome of the San Mateo County History Museum.

When: November 22, 2025 (10:00 AM-4:00 PM)
Where: San Mateo County History Museum, 2200 Broadway, Redwood City, CA 94063
Cost: Free admission

Blues artists Kid & Lisa Andersen perform in Courtroom A from 1:00-2:00 PM. Perfect for finding unique gifts and stocking stuffers.

Details: https://www.redwoodcity.org/Home/Components/Calendar/Event/910182569

Redwood City Winter Wonderland

Red Morton Community Center hosts an evening of holiday fun.

When: December 6, 2025 (5:00-7:00 PM)
Where: Red Morton Community Center, 1120 Roosevelt Ave, Redwood City, CA 94061
Cost: $10 Activity Band per child (Merry Marketplace free to attend)

Activities included:

Cookie decorating
Inflatables
Photos with Santa (bring your camera)
Hot cocoa station
Merry Marketplace where kids sell their holiday creations

Details:

Families exploring Redwood City appreciate these well-organized community events.

16th Annual Chanukah Festival

Courthouse Square hosts this festive celebration.

When: December 14, 2025 (4:00-5:15 PM)
Where: Courthouse Square, 2200 Broadway Street, Redwood City, CA 94063

Enjoy menorah lighting, music, latkes, and donuts.

Details: https://www.redwoodcity.org/Home/Components/Calendar/Event/908792569

Belmont Holiday Craft Faire

Over 70 vendors fill Twin Pines Park with handcrafted items.

When: November 22, 2025 (10:00 AM-4:00 PM)
Where: Twin Pines Park, One Twin Pines Lane, Belmont, CA 94002

Vendors set up in the Senior and Community Center, Lodge, Manor, Cottage, and a new outdoor location. Parking is limited, so walk or carpool if possible.

Details: https://www.belmont.gov/Home/Components/Calendar/Event/858216

Belmont Winter Wonderland Workshop

Kids ages 5-12 can drop off for supervised holiday activities.

When: December 6, 2025 (9:00 AM-12:00 PM)
Where: Twin Pines Lodge 125 Max 40, Twin Pines Lane, Belmont, CA 94002

Activities:

Ornament crafting
Cookie frosting
Letters to Santa
Hot cocoa

Parents can drop off and pick up at noon. Belmont Parks and Recreation staff and volunteers provide supervision.

Details: https://www.belmont.gov/Home/Components/Calendar/Event/850216

For homebuyers considering Belmont, these family-focused programs demonstrate the strong community support system.

Santa at the Firehouse & Toy Drive

Fire Station 14 hosts this annual event benefiting children in need.

When: December 11, 2025 (5:30-7:30 PM)
Where: Fire Station 14, 911 Granada Street, Belmont, CA 94002
Cost: Free, but bring at least one new, unwrapped toy

What's included:

Photos with Santa and holiday characters
Snow
Hands-on holiday crafts
Refreshments

Sensory-friendly session: 5:00-5:30 PM for youth with disabilities or those who benefit from a calmer environment. This early session features therapy dogs, activities, and a welcoming setting.

Details: https://www.belmont.gov/Home/Components/Calendar/Event/

What Winter Events Make San Mateo County Special During the Holidays?

The Sound of Music

The Pied Piper Players perform Rodgers & Hammerstein's beloved musical.

When: November 14-23, 2025
Where: Bayside Performing Arts Center, 2025 Kehoe Ave, San Mateo, CA

Over 70 talented Bay Area performers bring this story of love, courage, and music to life. Expect beautiful sets and classic songs like "Do-Re-Mi," "Sixteen Going on Seventeen," and "Climb Ev'ry Mountain".

Details: https://piedpiperplayers.org/shows/sound-of-music/sound-of-music-tickets

San Mateo Winter Wonderland

Central Park & Recreation Center hosts an indoor winter celebration.

When: Saturday, December 6, 2025 (5:00-7:00 PM)
Where: Central Park Recreation Center, 50 E. 5th Avenue, San Mateo

Activities:

Holiday music
Crafts
Festive photo opportunities
Cookie decorating
Hot chocolate

Activities may change due to weather.

Details: https://www.cityofsanmateo.org/3956/Winter-Wonderland

Families considering San Mateo real estate appreciate the city's commitment to free, accessible holiday programming.

The Hillsborough Show

This revival of the former Hillsborough Antique + Art + Design Show benefits United Veterans Services.

When:

November 7: 11:00 AM-1:00 PM (VIP), 1:00-6:00 PM (General Admission)
November 8: 11:00 AM-12:00 PM (VIP), 12:00-6:00 PM (General Admission)
November 9: 11:00 AM-4:00 PM (General Admission)

Where: San Mateo County Event Center, Fiesta Hall, 1346 Saratoga Dr, San Mateo CA 94403
Cost: Free general admission, $10 VIP tickets for early shopping on Friday and Saturday

Over 50 dealers showcase vintage, antique, and contemporary items including jewelry, linens, silver collectibles, art, and paintings.

Details: https://www.thehillsboroughshow.com

International Gem & Jewelry Show

America's longest-running direct-to-consumer gem and jewelry event comes to San Mateo.

When:

Friday: 12:00-6:00 PM
Saturday: 10:00 AM-6:00 PM
Sunday: 11:00 AM-5:00 PM

Where: San Mateo County Event Center, Expo Hall, 1346 Saratoga Dr, San Mateo, CA 94403
Parking: $18 with credit card, $20 with cash (no in/out privileges)

The coffee shop operates Friday 11:00 AM-5:00 PM, Saturday 10:00 AM-5:00 PM, and Sunday 11:00 AM-4:00 PM.

Details: https://www.intergem.com

Holiday Traditions for Mid-Peninsula Homeowners & Residents

Holiday events show you what a neighborhood feels like beyond the property specs. Walking Christmas Tree Lane or watching your kids frost cookies at a Winter Wonderland reveals the community connections that make a place feel like home.

For buyers exploring Mid-Peninsula communities, attending these celebrations offers authentic insight into different areas. The packed crowds at San Carlos's Night of Holiday Lights show community pride, while the volunteer-run programs demonstrate the hands-on spirit of these towns.

At Veritas Homes, we've represented properties throughout the Mid-Peninsula and know that home value comes from more than square footage. Strong communities and shared traditions matter. Through our Change Homes Change Lives program, we support causes our clients care about because the best neighborhoods are built on shared values.

The holiday season gives you the perfect reason to explore Menlo Park, Woodside, Hillsborough, Atherton, Redwood Shores, and Burlingame when they're dressed in their festive best. Whether you're considering a move or want to appreciate where you already live, these celebrations show what makes the Mid-Peninsula special.

Ready to find your perfect holiday destination? Browse active listings or contact our team to discover which Mid-Peninsula community fits your family best.