Late night San Mateo shines

Walking up B Street, there were groups of 20-somethings wandering around casually with drinks and soft serve in their hands. All of the public outdoor seating was taken and there was the faint sound of overlapping conversation in the air. People lingered in the space. The city felt alive, but not loud. Not overwhelming, just quietly bustling and energized. 

As we passed by a group of younger adults, I overheard one say to another, “Yeah, I love San Mateo. You wouldn’t know it unless you chose to stop here, but it’s a great city for food and people watching.” 

People watching. It’s such a specific kind of quiet joy. I used to love people watching when I was a newly minted working professional adult. Watching the world go by while sipping something, making up stories about strangers. And San Mateo, at least lately, offers a great show. Boba shops packed with students and co-workers, people riding scooters and bikes in slow, lazy circles around the vibrant mural that now anchors the closed-off stretch of B Street. There’s an easy air to it all, like the street closure created space not just for dining but also for lingering — for lives to bump up against one another. 

It’s a version of San Mateo that I hadn’t experienced in a long time, and I loved it. 

Over dinner, we were seated in the front room so I had a direct line to the entrance and saw a parade of takeout orders being scooped up every few minutes and a hum of young adults coming from workouts and others arriving in groups for dinner up until when we left at 10:30 p.m. On a Sunday! It felt, for a moment, like we had been dropped into a side street in Chelsea or the Lower East Side, not downtown San Mateo. 

Curious, I asked a few fellow diners where they had come from. “Oh, we live around here,” they said, like it should have been obvious. I suppose it should have been. 

During the day, families with young children, workers and retirees fill these same streets, doing their own version of meandering. They stop at parks, chase bubbles, read the Daily Journal at their favorite coffee shop, grab frozen yogurt, walk to the library and get all those errands done. Our family is typically a part of that crowd. We’re the blue-plate dinner special crew, aiming for the first seating so we can get our youngest to bed by 7 p.m. Because my husband and I had kids nearly seven years apart, it’s been our rhythm for well over a decade. We know the city by daylight: library trips, playgrounds, the earliest open breakfast spots and weekend farmers’ markets. 

I had lived that life for so long that I sort of assumed that San Mateo went to sleep after 9 p.m., but I was wrong. 

There’s a different San Mateo that awakens after dark. It’s alive with movement and music and chatter. It’s a younger city than I gave it credit for, one that’s found its rhythm and built its own kind of nightlife — not in clubs or raucous bars but in cozy restaurants, casual bars and long walks after dinner. A kind of intimate nightlife, where the goal isn’t to escape the city, but perhaps instead is to dwell in it more fully and connect with each other more deeply. 

What we see and love of a place is true and valuable, but it’s never the whole story. Cities hold layers and subcultures we may never encounter unless we intentionally step outside our own routines and rhythms to look for them. Sometimes that means staying out a little later than usual, taking a different route home, or saying yes to an invitation we’d normally decline. And sometimes, it’s just being curious. 

A city doesn’t have to choose one personality. It can be good for early dinners and late ones. For stroller mornings and lit-up scooters at night. For young adulthood, family life, retirement and everything in between.

I like this San Mateo — the one I saw this weekend, filled with stories and surprises. It reminded me that even after all these years, there’s still more to discover. And that’s a beautiful thing. 

Annie Tsai is chief operating officer at Interact (tryinteract.com), early stage investor and advisor with The House Fund (thehouse.fund), and a member of the San Mateo County Housing and Community Development Committee. Find Annie on Twitter @meannie.