Guides — Calendar

The year

What the city does, month by month, from the green hills of February to the warm nights of October.

Checked August 2026

San Mateo has two seasons that matter — wet and green, dry and gold — and a set of annual events that hang off them.

Winter, December to February

The rain arrives in systems, not drizzle. Between storms the air is scrubbed clear and the East Bay hills show in detail from the levee. The hills go green within about two weeks of the first real rain, which is the most dramatic thing the local landscape does.

Citrus is in at the farmers market. The reservoir fills. Trails are muddy and worth it. Lows in the forties mean the heating comes on, and old single-pane houses feel every degree.

Spring, March to May

The best hiking weeks of the year. Wildflowers along Crystal Springs and up Sugarloaf, everything green, days lengthening, and the marine layer not yet established. Little league fields fill up. By late May the grass has turned and the golden half of the year has begun.

Summer, June to August

Cooler than newcomers expect. Grey mornings, clearing to bright afternoons in the flats and sometimes not clearing at all in the hills. The Bay wind comes up around one o'clock every day — good for kiteboarders at Coyote Point, less good for anyone who set the table outside at six.

This is when the city's outdoor calendar runs: downtown street events, movies and concerts in the parks, and the county fair down in San Mateo at the event center, which has been an annual fixture for over a century. Fourth of July fireworks are visible from the shoreline, though the shows themselves have moved around over the years.

Fall, September to November

The actual summer. September and October bring the warmest, clearest, stillest weather of the year, and everyone remembers at once that their house has no air conditioning. Evenings stay warm enough to eat outside, which happens for maybe six weeks and then stops.

It is also the sharp end of fire season: offshore winds, low humidity, and the possibility of a public safety power shutoff in the hills. A planning matter rather than an alarming one.

By November the first rain has usually come, the air smells like wet eucalyptus, and the cycle starts again.

The recurring things

Dates and venues move, so these are categories rather than appointments: the Saturday farmers market on the hill, the county fair in early summer, downtown's street festivals, summer concerts in Central Park, and the winter holiday lighting downtown. The city's parks and recreation calendar is the reliable source.