Live it up this Labor Day: 20 local events for the long holiday weekend on the Peninsula

Concerts! Festivals! Food trucks! Monster trucks!! It’s The Six Fifty’s guide to winning Labor Day 2021.

THE SIX FIFTY Staff
THE SIX FIFTY
5 min readSep 2, 2021

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And so, summer draws to a close.

Kinda.

Whereas much of the country dives head first into cool autumn months, the Bay Area kicks off a whole calendar of seasonal (and still warm weather) events. In this sense, Labor Day weekend here on the Peninsula provides ample opportunity to live it up through the long weekend without the bittersweet feeling of summer gone by. Better yet, you can celebrate with everything from a monster truck show to a beer garden circus.

So get your game plan going, stay safe and check out the many happenings on this handy list for getting your holiday weekend dialed in.

The False Bottom Band!! (Images via Hop Dogma’s FB page)

Lotsa live music

Lots of live music this weekend. Check out our fave local bluegrass outfit — False Bottom Band when they play Old Princeton Landing in Pillar Point Harbor this Saturday.

The Saratoga Mountain Winery has concerts throughout the weekend in its swanky vineyard amphitheater. The horn-driven R&B veterans Tower of Power play on Friday night, followed on Saturday by a showcase of nostalgic pop with Lost 80s Live (Hey! Flock of Seagulls!) and classic rockers Chicago on Sunday.

Opera San José and Symphony Silicon Valley present two days of performances on the Tower Lawn at San Jose State University — for free!

And yes, Napa’s big annual Bottle Rock Festival — with the Foo Fighters, Miley Cyrus, Brandi Carlisle, Megan Thee Stallion and more — is indeed sold out, but extras are currently floating around on their ticket exchange page.

(Screenshot via Burn Week: Global Live Stream)

Festive festivals and festivities

Millbrae will be celebrating its 50th Art & Wine Festival with live music, crafts and a classic car show. Bring the whole family for a wide range of food and festivities…not to mention an entire Kid’s Zone. Runs Saturday and Sunday from 10 a.m. to 5 p.m.

Redwood City hosts a long weekend of Shakespeare in the Park. Head to downtown for the San Francisco Shakespeare Festival production of “Pericles, Prince of Tyre” on the Sequoia High School campus lawn.

Meanwhile, the Kings Mountain Art Fair virtually returns to celebrate local artists of many mediums. Live chat with the artists throughout the weekend and shop online.

Belmont’s Greek Festival has converted to a foodie footing this year with “Take N Bake.” Online orders are closed, but you can swing by all weekend for gyros and loukoumades.

Missing the Burn this year? Tune in online to get your Burning Man fix with a wide range of music and art, from the Dusty Multiverse to the Infinite Playa, or check out the new Burn Week: Global Live Stream which will feature a 24-hour Burn Night from September 4 to September 5.

Yeeeaah…..just your average Labor Day….with Monster Jam! (Image via Monster Jam’s Facebook)

Fun for the kiddos

If (like us) giant trucks crushing things speaks to your idea of Labor Day, then head over to SAP for Monster Jam to marvel at all manner of motorized mayhem in the mud. All weekend long.

Dig out the rods and tackle, Saturday is free fishing day. Take advantage of one of two days each year that the California Department of Fish and Wildlife allows you to fish for free without purchasing a license. You might even catch something!

Want to make memories the kids will never forget? This weekend….(cue high noon showdown music)… the SF Giants host the LA Dodgers in what has already shaped up to be the most exciting series of the year. Yes, the battle over the National League West goes into overdrive as the Giants and Dodgers clash….while tied for first place!

And, of course—donuts. Sunday is the last day to swoop on Krispy Kreme’s oh-so-sweet offer of two free donuts with proof of vaccination.

(Image via Getty)

Get a sitter (and a designated driver)

Hey-o…the good folks at Devil’s Canyon Brewing are throwing their M.A.D.E. in San Carlos bash this Friday. Yes, that stands for “music, art, dance extravaganza,” in which they turn Beer Friday into a lively beer-centric carnival with live music from Zydeco Flames, Monkey Ska and Bella Nota. Plus, belly dancing, circus stunts, food trucks and more.

If you’re more into the grapes than the hops, Savannah Chanelle continues its summer music series with acts playing throughout the long weekend and specials to match, featuring the Stan Erhart Band on Labor Day.

Or…head to Menlo Park for Left Bank Brasserie’s Friday Night live music series, have a beer to some ’90s/’00s tunes at Freewheel Brewing in Redwood City or check out Mark Bettencourt & the Aftermath at Murphy’s Law in Sunnyvale on Saturday.

Enjoy the long weekend, 6–5–0ers!

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THE SIX FIFTY Staff
THE SIX FIFTY

The best of what to eat, see and do on the SF Peninsula.