South Bay is a region in southern California, home to many popular cities such as San Jose and Sunnyvale. The Peninsula region of the San Francisco Bay Area lies south of the City and County of San Francisco, reaching from its famous neighbor to the north into high-tech Silicon Valley. The main county in this area is called “San Mateo”.

The South Bay/Peninsula has some of the most exciting and refreshing weekend fun events in all of California!

Most Popular Upcoming Events

SF’s Drag Queens on Ice 2021 (Union Square)

91st Golden Gate Park Tree Lighting w/ Carnival Rides + Snow (2021)

Japan’s Stunning “Dandelion Project” Light Show Comes to SF (Dec. 3 – Jan. 21)

SF’s 2021 “Italian Christmas Market” at Fort Mason (Dec. 4-5)

2021 “Sunset Holiday Mercantile” Golden Gate Park Pop-Up (Dec. 4-5)

Caltrain Holiday Train Whistle-Stop Tour: World’s Largest Toy Train | 2021

Downtown’s “Let’s Glow SF” Tall Building Light Festival (Dec. 3-12)

SF’s Lighted Forest Returns to Golden Gate Park on Dec. 2

31st Annual Hayes Valley Holiday Stroll + Block Party (2021)

Thrive City’s Outdoor “Winter Wonderland” 2021 at Chase Center

Saturday, December 4, 2021

South Bay

1. Caltrain Holiday Train Whistle-Stop Tour: World’s Largest Toy Train | 2021

Cost: FREE
When: December 4, 2021 – 4:00 pm to 8:20 pm
Venue: San Francisco Bay Area

Peninsula

1. Palo Alto Art Center Studio Holiday Sale 2021

Cost: FREE
When: December 4, 2021 – 4:00 pm to 8:20 pm
Venue: San Francisco Bay Area

2. Christmas Market at Allied Arts Guild (Menlo Park)

Cost: FREE
When: December 4, 2021 – 10:00 am to 4:00 pm
Venue: Allied Arts Guild
Address: Allied Arts Guild 75 Arbor Road Menlo Park, CA 94025

3. Hometown Holidays Redwood City 2021

Cost: FREE
When: December 4, 2021 – 10:00 am to 6:00 pm
Venue: Downtown Redwood City
Address: Broadway and Hamilton, Redwood City, CA

4. The Great Dickens Christmas Fair’s “Drive Thru Dickens’ London” Opening Day

Cost: $25
When: December 4, 2021 – 11:00 am to 5:00 pm
Venue: Downtown Redwood City
Address: Broadway and Hamilton, Redwood City, CA

Sunday, December 5, 2021

Caltrain Holiday Train Whistle-Stop Tour: World’s Largest Toy Train | 2021

Cost: FREE
When: December 5, 2021 – 4:00 pm to 8:20 pm
Venue: San Francisco Bay Area

Saturday, December 11, 2021

South Bay

Open Air Plant Market (San jose)

Cost: FREE
When: December 11, 2021 –  10:00 am to 5:00 pm
Venue: Santana Row
Address: 368 Santana Row, San Jose, CA

Peninsula

1. Wintry Redwood & Oak Tree Walk at Gamble Garden (Palo Alto)

Cost: FREE
When: December 11, 2021 –  10:00 am to 12:00 pm
Venue: Gamble Garden
Address: 1431 Waverley Street, Palo Alto, CA

2. Free Organic Espresso Liquor Tasting (Pacifica)

Cost: FREE
When: December 11, 2021 –  2:00 pm to 5:00 pm
Venue: Tripp Distillery
Address: 1121 Palmetto Ave., Pacifica, Ca

Saturday, December 25, 2021

Christmas Day at San Jose’s 2021 “Christmas in the Park”

Cost: FREE
When: December 25, 2021 –  12:00 pm to 12:00 am
Venue: Plaza de Cesar Chavez
Address: 194 South Market St., San Jose, Ca