Walk the 2000 block of Broadway on a Friday evening in mid-June and something will feel different. It won't be the music — Music on the Square has been running at Courthouse Square for twenty years, and the crowds know where to go. What will feel different is that the street itself will have changed. Earlier this month, the Redwood City City Council voted unanimously to introduce an ordinance allowing open-air alcohol consumption along a defined stretch of the Broadway Pedestrian Mall between Jefferson Avenue and Main Street. If it clears final approval, residents will be able to carry a drink from a participating restaurant out onto the block, into the evening, toward the music.
That detail is the clearest way to understand what is happening in Redwood City's downtown right now. The city is not simply scheduling events. It is changing what the street is allowed to be.
The Ordinance, and What Prompted It
The proposed entertainment zone covers the 2000 block of Broadway between Jefferson Avenue and Main Street, along with the section of Redwood Creek between Broadway and the Main Street parking lot. Council member Isabella Chu framed the intent at the special meeting: "The opportunity to add a little joy and whimsy into our events in downtown and throughout our city is really appealing." The vote to introduce the ordinance was unanimous.
The timing was described in the context of this summer's FIFA World Cup, which brings matches to the Bay Area and creates a communal-viewing calendar that cities are actively trying to host. Redwood City's Courthouse Square at 2200 Broadway has long been the city's gathering space for exactly these kinds of shared moments. The ordinance gives restaurants along that corridor a formal mechanism to activate the pedestrian mall rather than contain the experience inside a fenced patio or behind a door. The ordinance still needs final council approval, but the direction of the vote signals where this is heading.
The backdrop it lands against could not be better timed.
The Summer Series Turns Twenty
Redwood City's Summer Series begins May 29 and — this is the part that does not get enough attention — runs through November. That is not the usual shape of a municipal summer calendar. Most programs wind down after Labor Day. This one adds Oktoberfest in late September and the Zoppé Family Circus at the library parking lot from November 6 through 29.
The Redwood City Pulse reported the full 2026 calendar on May 18, two days before this post was written. It is the twentieth year of the series, and the programming reflects that milestone in volume and range.
The anchor is Music on the Square: free Friday concerts at Courthouse Square, weekly from May 29 through September 4. The season opens with Carnaval, moves through Boys of Summer, Bululú, Native Elements, Careless Whisper, and Mercy and the Heartbeats before closing with Pride & Joy. On Wednesdays, Music in the Park runs at Stafford Park. On Thursdays, Movies on the Square at Courthouse Square, with kids' films at 6 p.m. and independent or main features at 8 and 8:30 p.m. On select Saturdays, Pub in the Park at Red Morton Park.
The standalone events layered through the season:
- May 29: Season opener, Music on the Square
- June 12: Art on the Square, Hamilton Ave at Courthouse Square, 5–8:30 p.m. — its own 20th-anniversary season, with three more shows July 10, July 24, and August 28
- June 27: Classical Music on the Square, Redwood Symphony performance, 7 p.m.
- July 3–4: Chalk Festival, all day downtown
- July 4: Independence Day parade at 10 a.m.; fireworks at the Port of Redwood City, 6–10 p.m.
- August 15: Picnic en Blanc
- August 15–30: Shakespeare in the Park, "Antony and Cleopatra," Saturdays and Sundays at 6 p.m., Red Morton Park
- August 29: Lebanese Festival, 10 a.m.–3 p.m.
- September 13: Fiesta Patrias
- September 18–20 and 22–27: Oktoberfest Redwood City
- November 6–29: Zoppé Family Circus, Redwood City Public Library parking lot (ticketed)
Most of this is free. The programming does not treat September as the finish line, which gives the whole season a different weight than it carried in earlier years.
What's Opened Along Broadway
The event calendar has a different street to land on than it did five years ago. Since mid-2024, a notable run of independent businesses has opened along Broadway and nearby streets, and they change what residents find when they arrive early or stay late.
Bay Burgers (976 Woodside Rd) opened in March 2026. Chef-owner Xavier Pereznegron is a Redwood City native who spent years in fine dining before launching a smashburger pop-up at Hoover Park in the summer of 2024. The pop-up sold out every weekend. The brick-and-mortar carries rotating weekly specials, smoked meats, agua frescas, and milkshakes alongside the core menu.
The Baker Next Door (Main Street) opened in August 2024 under head baker Luis Lujan. The bakery is known for a boule with green olives, asiago, and thyme, and a pain suisse with vanilla pastry cream and dark chocolate — the kind of anchor that pulls weekday mornings toward a destination rather than a drive-through.
DeVine Wine & Beer (2627 Broadway St) opened in late 2025. Owner Ingrid Campos took over the former BottleShop space and built a curated wine and craft beer shop around food pairings.
Fireside Books & More (2421 Broadway St) opened February 1, 2025. Founders Andrew Johnson and Taylor Kubota stocked the shelves with books, cards, and locally crafted goods including birdhouses by LeighLee's Garden and jewelry by Wandergrove.
Mazra (Broadway) reopened in October 2024 following a kitchen fire and continues serving the wood-fired kebabs and shawarma it was known for before the closure.
The list also includes Das Bierhauz, a German beer garden; Limón, a Peruvian restaurant that opened in October 2024; and Inshou, a dim sum and modern Cantonese spot drawing strong early attention in 2026. These businesses are not all in the same block or the same price range. What they share is independent ownership and, in several cases, operators who are from here or have been operating in the Bay Area long enough to understand what this particular street needs.
Why 2026 Is the Summer to Track
The Summer Series has worked for twenty years because Courthouse Square is a genuinely good public space and because Redwood City has been consistent about showing up and programming it. That is the baseline. What is different in 2026 is that three things are converging for the first time at once.
The programming is longer and denser than it has been. The businesses that line the approach and surround the square have more character and more staying power than the ones that preceded them. And the city is actively changing the legal architecture of the street to make it function more like the kind of downtown where people linger — not because there is nowhere else to go, but because the street itself rewards staying.
The outdoor drinking zone is a small regulatory change. Its effect on a Friday evening in August, when Music on the Square is running and the Redwood Symphony has already played that week and Bay Burgers is two blocks away, is not small at all. That is the specific combination 2026 is assembling.
If you live here, the season starts May 29. You already know where Courthouse Square is. What is worth knowing now is that the street around it is being built into something different, and this is the summer it becomes visible.
Hummingbird Homes works with buyers and sellers throughout Redwood City and across the Mid-Peninsula. Keyko and Monica bring deep local knowledge and a straightforward approach to every transaction. Reach out whenever you're ready to talk.
