The Weekend San Carlos Avenue Becomes a 225-Booth Art Fair

By 9 a.m. on October 10, the curb parking on San Carlos Avenue will already be gone, not because every resident found a spot, but because there won't be a curb left to park on. Canopy tents go up where cars usually sit. A stage gets built where the crosswalk usually is. For one weekend a year, the street that carries the Sunday farmers market and the after-work crowd at Devil's Canyon Brewing Company turns into something closer to a small county fair, and it's the 34th time San Carlos has done exactly this.

The thing worth understanding about the San Carlos Art & Wine Faire isn't the size of the crowd. It's that the crowd shows up on a street that already does this kind of work every single week, just at a smaller scale. The Faire doesn't invent foot traffic on Laurel Street and San Carlos Avenue. It's the loudest version of a job those two blocks have been doing for years.

Two Streets, One Recurring Job

The Faire's footprint runs along San Carlos Avenue and down the length of Laurel Street to Arroyo, closing both to traffic for the weekend of October 10 and 11, 2026, from 10 a.m. to 6 p.m. each day. That's a big ask of a downtown this size, but it's not a new ask. The same stretch of Laurel Street already hosts a farmers market every Sunday of the year, 9 a.m. to 1 p.m., with produce, flowers, and local vendors setting up on the same asphalt the Faire will later fill with 225 booths.

Put side by side, the difference is mostly a matter of degree, not kind.

A resident who already routes their Sunday morning around the farmers market has the closest thing to a dress rehearsal for what October 10 and 11 will look like, just scaled up by a factor the market never approaches on its own.

Thirty-Four Years on the Same Two Blocks

The Faire's run to a 34th year says something about how the event has grown into its footprint rather than shrunk to fit it. These days it's produced by the City of San Carlos in partnership with the Parks and Recreation Foundation of San Carlos, a shift from the Chamber of Commerce production longtime residents remember from earlier years. The vendor count has held in the low 200s for several recent years running, and this year lands at 225 artists, crafters, and specialty food vendors spread across both streets.

Three stages keep music going across both days, a scale the weekly farmers market has never needed and doesn't attempt. There's also a Family Fun Zone built specifically for the kind of hands-on activities that don't belong at a produce stand, which is really the clearest marker of how far this event has moved from its market-day roots into something closer to a proper festival.

The Regulars Don't Need a Festival Badge

What makes the Faire work isn't just the out-of-town vendors driving in for the weekend. It's that Laurel Street already has anchors who don't need an introduction. Domenico Winery has been producing Cal-Italia varietals on the street for more than 20 years and already runs its own calendar of ticketed tastings throughout the year. Devil's Canyon Brewing Company has a covered back patio and a lineup of programming that ranges from breadmaking classes to comedy nights, none of which depends on the Faire to draw a crowd. Hapa's Brewing Company has built a following around its own recurring trivia night, a fixture that has nothing to do with October.

For the newer arrivals, this year is different. Highlands Sports Bar & Grill, opened by longtime Laurel Street bar owner Christian Conte in the space that used to house Sneakers American Grill, will be working its first Faire weekend. So will Elia Restaurant, which took over the former Taurus space under co-owner Fatih Ulas, who already runs three other Elia locations around the Bay Area. Esnaf, the Turkish restaurant that moved into the old Cuisinett space, joins a street that has historically leaned Italian and Greek. None of these three needed the Faire to justify signing a lease here. The Faire is simply the first time their doors will be open for it.

That's the pattern worth noticing. The businesses that make Laurel Street worth visiting on a random Tuesday are largely the same ones that will be standing behind their own counters during the Faire, not renting booth space to compete with it.

Getting There Without Losing Your Spot

The parking crunch isn't hypothetical. In 2024, turnout was heavy enough that every open parking space for blocks around downtown filled up, which is part of why the city runs a shuttle system rather than leaving attendees to fend for themselves. A few things are worth building into a weekend plan:

• Free shuttles run roughly every 30 minutes from the Palo Alto Medical Foundation lot on Industrial Road, dropping off at the 500 block of Laurel.
• Bike valet parking is available for anyone riding in instead of driving.
• Caltrain and SamTrans both stop close enough to downtown to skip the parking question entirely.

None of this is exotic logistics. It's the same shuttle-and-transit approach the city leans on for any event that draws more people than downtown parking can hold, and the Faire is the biggest test of that system all year.

One Weekend on a Longer Calendar

The Faire lands in the middle of a stretch of downtown programming rather than standing alone. Burton Park still has a movie night scheduled for September 19, ahead of the Faire weekend. Laurel Street's Life on Laurel pop-ups continue to bring smaller-scale happenings downtown outside of the two big festival days. Trunk-or-Treat follows on October 30, and the city's holiday event, complete with snow on Laurel Street, closes out the year on December 4.

None of these are competing with the Faire. They're proof that San Carlos Avenue and Laurel Street are built to carry a full calendar of civic life, from a May parade route through a weekly Sunday market to a two-day fall festival that briefly turns the whole downtown into a single outdoor room. The Faire is the loudest weekend on that calendar, not the exception to it.

If you already live near enough to walk to Laurel Street this October, the only real planning question is which stage to park yourself in front of first. For anyone weighing whether a street with this kind of year-round pull is the right fit for a move to San Carlos, that's a longer conversation, and it's one the Laugesen Team has spent years having with families across the Peninsula. Reach out anytime to request a complimentary market and home valuation, no festival badge required.