San Francisco has no shortage of street festivals—but the Union Street Festival hits differently. Maybe it’s the Cow Hollow backdrop, with its mix of historic homes and chic storefronts. Maybe it’s the perfect early-summer timing, when the fog lifts just long enough for sunshine to wash over the Victorian-lined streets. Or maybe it’s just the simple, underrated joy of neighborhoods coming alive together—block by block, booth by booth.
This annual event transforms Union Street into a colorful corridor of local flavor, where art, music, and good food flow as freely as conversation. And it’s not just for locals—although plenty show up—it’s a gathering that feels like San Francisco itself: eclectic, expressive, and effortlessly cool.
Where It Happens: Cow Hollow, the Neighborhood with Hidden Depth
Don’t let the name fool you—Cow Hollow is far from pastoral these days. Once a literal cow grazing ground in the 1800s, it’s grown into one of San Francisco’s most beloved and walkable neighborhoods. It balances upscale charm with laid-back ease—think leafy streets, stylish boutiques, sidewalk cafés, and neighbors who actually say hello.
Union Street runs through the heart of it all, lined with restored Victorians that house everything from yoga studios to cocktail bars. During the festival, this strip becomes the stage for a lively two-day celebration where local makers, performers, and residents all share the spotlight.
Live music pulses through the heart of Cow Hollow as local bands take the stage at the Union Street Festival. Photo credit: Trap Speed 1320
What to Expect: Creativity, Culture, and Community on Every Corner
The Union Street Festival is one of those rare events that actually delivers on its promise of being “fun for all ages.” Whether you’re into live music, hands-on art, or just want an excuse to wander with a cold drink in hand, there’s a little something for everyone.
Music That Moves You
There’s no single stage—music spills out from every corner. Acoustic sets by rising local talents, full bands jamming near the beer garden, maybe even a saxophone solo drifting above the hum of the crowd. It’s spontaneous and soulful—more block party than concert, and that’s exactly the charm.
Art That Doesn’t Just Hang There
This isn’t a gallery—it’s a living, breathing street exhibition. Bright murals unfold in real time as visitors help paint them, while artists display everything from hand-thrown ceramics to oil portraits. Creativity is hands-on here. You’re not just admiring art; you're part of it, whether you're holding a brush or just soaking it all in.
Local Makers, One-of-a-Kind Finds
Booths stretch for blocks, each one a little world of its own—vintage clothes, hand-stitched bags, small-batch skincare, and quirky home goods you won’t find anywhere else. It’s the kind of place where you find your new favorite candle by accident or pick up a statement necklace that somehow becomes a staple.
Food and Drink: From Gourmet to Classic Street Eats
The scent of sizzling skewers and fresh churros floats through the air. There’s global cuisine on one end, vegan bites on the other, and somewhere in the middle? Frozen treats, craft beers, and yes—wine slushies that are as refreshing as they are cheeky. It’s casual, it’s delicious, and it feels like summer in a cup.
Everyone’s Invited—Even the Dogs
This isn’t a leave-the-pets-at-home kind of event. Four-legged companions stroll happily beside their humans, and there’s plenty of space for kids to run, sketch with sidewalk chalk, or dive into family-friendly activity zones.
Community mural in progress at the Union Street Festival. Photo credit: Div Manickan
Why It’s Worth Coming Back Every Year
Sure, you could technically describe this as a street fair—but it’s really more like a snapshot of what makes San Francisco work when it works best. The Union Street Festival captures that rare, intangible thing: a sense of belonging, even if you’re just passing through.
And once the booths are packed up and the music winds down, Cow Hollow is still here—inviting, walkable, and full of charm that lasts long past the weekend. For anyone considering life in this pocket of the city, it’s a great way to feel the rhythm of the neighborhood, meet local makers, and see how connected and alive this community really is.
🡒 Curious about the area? Explore our Cow Hollow neighborhood guide or check out available properties nearby to get a deeper look at what life’s like around Union Street.
Final Thoughts: More Than a Festival—It’s a Feeling
The Union Street Festival isn’t about spectacle. It’s about the everyday magic that happens when neighbors show up, artists share their craft, and streets fill with music, laughter, and the kind of small joys that linger long after the weekend is over.
So whether you’re a longtime local or new to the city, this festival is worth a wander. And if you fall in love with the neighborhood while you’re there? You wouldn’t be the first.
🡒 Want to see more of what San Francisco’s neighborhoods have to offer? Check out our full real estate blog or browse listings in Cow Hollow and the Marina District to see if this community feels like home.