Every Tuesday afternoon, a parking lot behind Westfield Fashion Square fills with folding tables, a live band nobody had to pay to see, and a rock climbing wall that has been drawing kids away from their parents' shopping carts for over three decades. Eight weeks from now, on Sunday, October 18, Ventura Boulevard itself will shut down for nine blocks and absorb a crowd that, in recent years, has topped out somewhere around 100,000 people.
Same zip code. Same general stretch of pavement. Almost nothing else in common.
If you have lived in Sherman Oaks for any length of time, you already know both of these exist in some fuzzy way. What's less obvious is how differently they're built, who runs them, and why one basically never changes while the other reinvents itself every year. That difference tells you something real about how this neighborhood organizes its own social life.
The two traditions, side by side
| Sherman Oaks Farmers Market | Sherman Oaks Street Fair | |
|---|---|---|
| When | Every Tuesday, year-round | One Sunday each October (Oct. 18, 2026) |
| Where | Westfield Fashion Square parking lot, 14006 Riverside Dr. | Ventura Blvd. between Van Nuys Blvd. and Kester Ave. |
| Run by | Raw Inspiration, a certified market operator | Sherman Oaks/Encino Chamber of Commerce |
| Scale | A few dozen stalls, one small stage | Up to ~200 vendor booths, multiple stages |
| Crowd | Regulars doing their weekly shopping | As many as 100,000 people over the day |
| Signature detail | Free live band every week, kids' rock wall | The "Cham-BAR," four bars combined into one outdoor lounge |
The market is a habit. The fair is an event. Neither one is trying to be the other.
The Tuesday habit nobody advertises
The Sherman Oaks Farmers Market has been running since 1991, which makes it older than most of the businesses currently open along Ventura Boulevard. It sets up in the Westfield Fashion Square lot on Riverside Drive every Tuesday afternoon, typically from around 2 to 6 (some listings stretch that into early evening during summer), and it's operated by Raw Inspiration, the same certified market operator that runs the Tuesday market at CSUN in Northridge and the Saturday market in La Cañada Flintridge. That's not a small neighborhood volunteer effort. It's part of a network that knows how to run a weekly market without it ever feeling like an event you had to plan for.
What sets this one apart from a standard produce stand rotation is the entertainment built into it. There's a live band every week, and it's free, which the market's own description leans on as something other Valley markets don't consistently offer. There's a kids' area with a rock climbing wall and an inflatable obstacle course, which turns a produce run into an actual after-school stop for families who live nearby. The market also accepts EBT, so it functions as a real grocery option for the neighborhood, not just a Tuesday diversion.
None of this requires advance planning. You don't need to check a lineup or buy a ticket. You show up, and whatever's playing that week is what's playing.
The one Sunday that takes over the boulevard
The Street Fair works on the opposite logic entirely. It happens once a year, it's run by the Sherman Oaks/Encino Chamber of Commerce rather than a market operator, and it treats Ventura Boulevard itself as the venue instead of a parking lot off to the side.
This year marks its 34th edition, scheduled for Sunday, October 18, 2026, running the length of Ventura Boulevard between Van Nuys Boulevard and Kester Avenue. Recent years have counted vendor booths in the 150 to 200 range, spread across food, artisan goods, and Chamber-member businesses. Past editions have drawn crowds as large as 100,000 people over the course of a single day, which the fair's organizers bill as the largest single-day event in the San Fernando Valley.
The programming reflects that scale. There's a main stage with continuous live music (last year's lineup included a headline set from a former American Idol finalist), a separate Community Stage where local elementary, middle, and high school students perform, a Pet Zone with adoption groups from local rescue organizations, antique fire trucks from the LAFD Historical Society, classic car displays, and carnival attractions including a Ferris wheel. There's also the detail that tends to get people talking afterward: the "Cham-BAR," where four of Sherman Oaks' bars combine forces to run a single outdoor cocktail lounge for the day.
If you're planning to go, the one piece of practical advice worth repeating is about parking. Regulars have learned the hard way that the residential side south of Ventura is largely permit-only, and cars left there during the fair have ended up ticketed or towed. Westfield Fashion Square's own lot, the same one the Tuesday market uses, tends to be the safer bet.
Why the contrast matters more than either event alone
Here's the part that's easy to miss if you only ever hear about the big one. The fair gets the press coverage and the 100,000-person headline number, but it's the market that's been running, unbroken, every single week since before most current residents moved in. One is built for scale and spectacle. The other is built for consistency. A neighborhood that can sustain both, a low-key weekly ritual for over three decades and an annual event that keeps growing large enough to shut down its main boulevard, is telling you something about how deeply these habits are woven into daily life here. It's not that one event replaced the other or that the Chamber's fair grew out of the farmers market. They exist on entirely separate tracks, run by different organizations, for different reasons, and Sherman Oaks residents just move fluidly between both without treating it as unusual.
That's a different kind of neighborhood texture than a single flagship event that everyone points to when asked "what's Sherman Oaks known for." It's two answers, at two different volumes, and most people who live here only really think about the loud one until they're reminded the quiet one has been there the whole time.
If you're curious what else is changing along that same stretch of Ventura Boulevard this year, from a food and restaurant standpoint, we mapped the newer arrivals in a separate piece on this year's openings. Between the new restaurants, the Tuesday market, and one very loud Sunday in October, this stretch of the boulevard does a lot more than most people give it credit for.
Plan around whichever one fits your week
If you want the low-commitment version, the Tuesday market doesn't require any planning at all. Swing by the Westfield Fashion Square lot on Riverside Drive most Tuesday afternoons and there will be produce, a band, and something for the kids to climb on.
If you want the full-immersion version, block off October 18. Get there early if you're driving, park at Westfield rather than on residential streets south of Ventura, and budget the whole afternoon. Vendor booths alone can take a while to work through, and that's before the stages, the Pet Zone, or the Cham-BAR come into play.
Either way, both of these belong to the neighborhood in a way that has nothing to do with home values or school boundaries. They're just what Tuesdays and one particular Sunday look like here.
For more on what makes specific pockets of Sherman Oaks tick, from the boulevard's newer restaurant openings to how pricing actually breaks down north and south of Ventura, the Sherman Oaks neighborhood page on our site keeps a running record. And if you're weighing a move into the area and want a read on how a specific block or building fits your budget and your routine, Robert Ramos is happy to walk through it with you. Book a free neighborhood strategy call whenever you're ready.
