If you’ve lived in the Bay Area for more than five minutes, you know the drill. Street fairs are basically a rite of passage. But honestly? Most of them feel like carbon copies of each other. You get the same lukewarm garlic fries, the same "live" cover bands playing Don't Stop Believin', and the same mass-produced trinkets that were definitely not handmade. The Art and Wine Festival Millbrae is different. It’s got this weird, charming, small-town energy that manages to survive despite being right next to one of the busiest airports in the world.
Millbrae is often just that place people pass through on the way to SFO or where they grab dim sum on a Sunday morning. But for one weekend in September—usually Labor Day weekend—the city transforms Broadway into this massive, pulsating artery of creativity and, let's be real, pretty decent booze. It’s been running for over 50 years. That’s not a typo. Fifty years of history means they’ve figured out the logistics that make other festivals a nightmare.
What Actually Happens at the Art and Wine Festival Millbrae
People show up for the wine, sure, but the art is what keeps you walking. We're talking about roughly 250 professional artists and craftspeople. These aren't just hobbyists. The Millbrae Chamber of Commerce, which organizes the whole thing, is notoriously picky about who gets a booth. You’ll see hand-blown glass that looks like it belongs in a gallery in Sausalito, intricate woodwork, and photography that actually captures the grit of the California coastline.
It's crowded. Very crowded.
If you hate shoulder-to-shoulder walking, show up at 10:00 AM sharp on Saturday. By 2:00 PM, the "wine" part of the Art and Wine Festival Millbrae title starts to take over, and the vibe shifts from "browsing for a new centerpiece" to "dancing in the street to a Santana tribute band."
The Drink Situation
Let’s talk about the glass. You can't just walk up and buy a drink. You have to buy the commemorative sturdy plastic wine glass or beer mug first. It’s a bit of a steep entry price if you only want one drink, but it becomes your ticket to the tastings. They usually feature a mix of local NorCal heavyweights and smaller labels. Think Sonoma Chardonnays, bold Napa Cabs, and an increasing number of craft brews from the burgeoning Peninsula beer scene.
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Microbrews have really stepped up their game here lately. While the wine used to be the star, the beer garden near the South Stage has become the unofficial headquarters for people who want to avoid the more frantic parts of the main drag.
The Logistics Most People Mess Up
Parking is a disaster. There’s no sugar-coating it. If you try to park within three blocks of Broadway, you're going to have a bad time. The smart move—the move that locals swear by—is taking BART or Caltrain. The Millbrae station is a massive transit hub, and it’s a very short, flat walk to the festival entrance.
If you absolutely must drive, aim for the residential streets west of El Camino Real, but check the signs. The city is aggressive about towing during festival weekend. They have to be.
Why the Food Matters More Than You Think
Street food is usually a gamble. But at the Art and Wine Festival Millbrae, the food vendors are a mix of traveling festival pros and local Millbrae staples. You’ll find the standard gyro and corn dog stands, but keep an eye out for the local Asian-fusion booths. Millbrae has some of the best food in San Mateo County, and some of those brick-and-mortar spots set up shop outside for the weekend.
It’s worth skipping the first three booths you see. Walk deep into the festival before you commit your appetite.
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It’s Actually Family Friendly (Seriously)
A lot of "Art and Wine" events are basically just outdoor bars where kids look miserable. This one actually tries. There’s usually a "Kids' Zone" with things like bungee jumping, giant slides, and face painting. It’s far enough away from the main stages that you don't feel like you're bringing a toddler to a mosh pit, but close enough that parents can swap out for a wine run.
The 2026 circuit is expected to lean even harder into the "Makers" movement. Instead of just looking at art, there are more interactive booths where you can see someone actually throwing clay on a wheel or soldering jewelry. It adds a layer of authenticity that keeps the event from feeling like a giant outdoor mall.
The Music Scene
There are usually two main stages. One is usually located at the north end of Broadway and the other at the south. The talent scouting is surprisingly good. You get the big-name Bay Area cover bands—the ones that draw huge crowds at the state fair—but they also mix in some original local acts.
- The Main Stage: Expect high-energy funk, soul, and rock.
- The Secondary Stages: Often more acoustic, jazz, or world music.
If you want to sit, you’re mostly out of luck. People bring folding chairs and park them in front of the stages early. If you didn't bring one, prepare to stand or find a patch of curb.
Why This Festival Still Matters in 2026
In an era where everything is digital and you can buy "handmade" art on Etsy with three clicks, there’s something visceral about the Art and Wine Festival Millbrae. You’re smelling the charcoal from the BBQ pits. You’re touching the texture of a canvas. You’re actually talking to the person who spent forty hours making that leather bag.
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It’s a community anchor. For the city of Millbrae, this is their Super Bowl. It funds a lot of the Chamber's work throughout the year. It supports the local shops on Broadway that otherwise struggle against the convenience of online shopping. When you buy a glass of wine here, you’re basically keeping the lights on for local civic programs.
Common Misconceptions
People think it’s free. Well, entry is free. You can walk the whole length of the festival without spending a dime. But if you want the "experience," it’s going to cost you. The glass, the tokens for drinks, the artisan food—it adds up fast. Budget at least $60 per person if you plan on eating and having two drinks.
Another myth? That it’s only for seniors. While the morning crowd definitely leans older, the afternoon is a total mix of Gen Z foodies, young families, and people who just want an excuse to day-drink in the sun.
Essential Survival Tips for Your Visit
- Hydrate. The Peninsula can get weirdly hot in September. The asphalt on Broadway radiates heat. Buy water early or bring a reusable bottle.
- Bring Cash. A lot of the smaller artists still prefer it, and it makes the drink token lines move way faster.
- Sunscreen is non-negotiable. There is almost zero shade on the main street. You will get burned while standing in line for a crab roll.
- Check the BART schedule. Weekend service can be spotty, and you don't want to be stranded at the station with three heavy bags of pottery.
Making the Most of the Experience
If you’re looking to actually buy art, go on Saturday morning. The best pieces—the unique, one-of-a-kind items—are usually gone by Sunday afternoon. Artists are also more willing to chat about their process before the crowds get overwhelming.
If you’re there for the party, Sunday afternoon is your time. The energy is higher, the bands are usually the headliners, and there’s a sense of "last call" for the summer.
Next Steps for Your Trip:
- Mark your calendar: Check the Millbrae Chamber of Commerce website for the specific Labor Day weekend dates and the 2026 band lineup.
- Plan your transit: Download the Clipper app to your phone now so you aren't fumbling at the BART kiosk when you arrive.
- Scope the map: The festival layout changes slightly every year; look for the digital map release a week before the event to locate your must-see artists.
- Book local: If you're coming from out of town, grab a hotel near the Millbrae station early, as they fill up with vendors and tourists months in advance.