I'm Jason, born and raised in San Mateo. My parents got their start in a small house on Idaho Street, and once my older siblings came along and the family needed more room, we settled on the Westside, in the house next to the plumbing supply store. The old Togo's on the block is El Nayarita now. I was born at Mills, went to Sunnybrae for kindergarten, then St. Matthew's from first through eighth (my first job, at fourteen, was answering their phones while I did my homework). We moved over to Shoreview in sixth grade, and I graduated from Aragon.
Being a kid here meant biking to Central Park for rec baseball, being a little too big for the kids' train, and grabbing a snow cone from the stand under the bleachers after. Birthday parties at Farrell's, the free birthday scoop at Baskin-Robbins on 3rd, Thrifty cones on B Street. Sundays fishing under the San Mateo Bridge with the family, or Bay Meadows with the cousins, cutting through the tunnel to the playground.
My second job was at the Peninsula Regent on Baldwin, busser to waiter to prep cook. Half the high school worked there back then, and I'm still friends with people I met on that job.
I never left, and I don't plan to. You'll still catch me on the Bay Trail off 3rd or grabbing a drink downtown at O'Neill's. That's the whole reason this guide exists. It's not an agency with a spreadsheet. It's a guy who grew up on these streets telling you where to actually go.