If you think September signals a slowdown in fairs and festivities, think again. Labor Day weekend marks the return of three annual longtime events: the Kings Mountain Art Fair, Belmont Greek Festival and Millbrae Art & Wine Festival. From there it’s a mix of end-of-summer traditions and fall favorites the rest of the month, including Oktoberfest celebrations (yes, in September), the Mid-Autumn Festival and the Great Glass Pumpkin Patch. Consult our Peninsula-wide events guide for a September to remember. All events are free unless otherwise noted.
Festivals, fairs and parties
The Belmont Greek Festival is back Aug. 31-Sept. 1 (admission is $5 for adults, $3 for seniors and children 13-17, kids 12 and under free with an adult). Enjoy live Greek music and dancing, mythology plays, craft boutiques and Greek food favorites like loukoumades, spanakopita and gyros. Find take-and-bake frozen entrees and freshly baked pastries for sale to bring home.
The Millbrae Art & Wine Festival returns Aug. 31-Sept. 1 with live music, artwork by nearly 300 artists, kids’ rides and food and drinks.
The Kings Mountain Art Fair showcases fine art from local artists among the redwoods above the town of Woodside Aug. 31-Sept. 2. Preview and shop from participating artists on the fair’s website.
Local Oktoberfest celebrations kick off at Gourmet Haus Staudt in Redwood City with a full weekend of beer, brats and polka Sept. 7-8, followed by Oktoberfest happenings in downtown Redwood City Sept. 20-22 and Sept. 24-29, Ludwig’s Biergarten in Mountain View Sept. 20-21 and Sept. 27-28 and Taplands in Santa Clara Sept. 29 (check websites for pricing). Click here for a complete guide to Oktoberfest on the Peninsula.
The Mountain View Art and Wine Festival Sept. 7-8 features kids’ activities, Italian street painting, a collaborative paint temple, live music and DJs, a lounge with a giant LED screen showing football and baseball games, a community talent stage and more than 400 artists selling a wide variety of artwork. Food and drink options include everything from Oaxacan cuisine and barbecue to wine and beer.
September Nights on B Street will feature an outdoor dining pavilion, dancing, a children’s play area and drinks available for purchase Sept. 12 and Sept 19 in San Mateo.
Try bites from local restaurants and listen to live music at the Taste of Los Gatos Sept. 14 (event free, tasting tickets $48.47).
Fiestas Patrias, a celebration of Mexican independence, is scheduled for Sept. 14 in South San Francisco with Aztec dancing, ballet folklorico, mariachi, Mexican snacks and more.
The 2024 San Mateo Autumn Moon Festival Sept. 14 will kick off with a 1-mile morning walk, followed by live music, food and family-friendly activities.
The 42nd annual Santa Clara Art & Wine Festival returns Sept. 14-15 in Central Park with over 160 arts and crafts vendors, live entertainment, a “Kids Kingdom” and festival food and drinks.
The Millbrae Mid-Autumn Festival Sept. 14-15 will feature more than 150 food and arts vendors, a large kids’ zone, and live music and entertainment.
The Los Altos History Museum will host the Mid-Autumn Festival in its courtyard Sept. 15 ($10 admission; museum members, seniors over 65 and children 12 and under free). A Chinese tradition also known as the Moon Festival, it originated as a way for people to thank the moon for the harvest and now symbolizes family reunions, according to the museum. The festival includes activities for all ages: crafts, traditional Chinese sports, live music and dancing.
Redwood City‘s Fiestas Patrias celebration is Sept. 15. Courthouse Square will be bustling with ballet folklorico dancing, live mariachi music, authentic Mexican food, arts and crafts vendors, a kids’ area and more.
Caltrain is hosting launch parties for its electrified service Sept. 21 in Palo Alto and Sept. 22 in San Mateo. Celebrations will include free Caltrain rides, food trucks, photo booths, games, giveaways and performances. Additional Caltrain stations will also be hosting activities and offering giveaways; check their website for complete details.
Sample harvest bounty, check out garden demos and the historic Immigrant House, and bring the kids for children’s activities at the Harvest History Festival Sept. 21 in Mountain View.
South San Francisco‘s annual Concert in the Park: Community Fun Fest is Sept. 21. Spend a day listening to live music, including a performance by the Grammy Award-winning musical group Daz Band. The event will also include kids’ activities, wine and beer sales, vendor booths and food trucks.
Summer’s End Music Festival takes place on the last day of summer, Sept. 21. Enjoy a full day of live music in Half Moon Bay and activities such as an inflatable obstacle course, caricatures and henna tattoos.
Train Days returns for two days of model trains at the Los Altos History Museum Sept. 21-22 (admission is $10; free entry for museum members and children 12 and under). Expert model railroad enthusiasts will be on hand to answer questions about their trains, and visitors can purchase food, train-related gifts and family portraits created by a live portrait artist on-site.
Peninsula Book Collaborative in Daly City hosts its annual fundraiser, the Banned Book Bash, Sept. 28 ($20 a person, free for educators). Banned books will be available for purchase, and there will be a reception with light refreshments and a silent auction.
The Great Glass Pumpkin Patch features over 10,000 glass pumpkins hand-blown in all shapes, colors and sizes. Head to the Palo Alto Art Center Sept. 28-29 to peruse and purchase pumpkins, as well as check out glass-blowing demos all weekend.
The September Arts & Culture Fest in downtown San Mateo Sept. 28 is a daylong event with local musicians, entertainment, cultural performances, family-friendly activities, 40 art vendors, and food and drinks.
Indie Author Fest is back for its second year Sept. 28 in Foster City. Join San Mateo County Libraries for a book fair, literary readings from local writers, and expert advice on writing and publishing.
The Sunnyvale Mid-Autumn Festival is Sept. 28-29 at Cityline Sunnyvale. Over 100 vendors will be on hand selling art and food, and live performances will include dancing, music and a kung fu show.
Pacific Coast Fog Fest returns to Pacifica‘s Palmetto Avenue Sept. 28-29 with over 200 arts and crafts booths selling handmade wares, live music, food and drinks, a parade under the theme “A Whale of a Good Time” Sept. 28, the Fall Family Fun Fest Sept. 29 and the Fog Jog Run and Stride Sept. 29 (Fog Jog registration $25).
Outdoor entertainment and recreation
The final Pub in the Park of summer is Sept. 7 in Redwood City, featuring an inflatable pub serving beer and cider, live bluegrass music from Wildcat Mountain Ramblers, food trucks and lawn games.
Join a beginner-friendly group bike ride with Silicon Valley Bicycle Coalition to Pub in the Park in Redwood City Sept. 7.
San Mateo hosts its 2024 Family Fun Ride and Bike Rodeo Sept. 7, featuring a guided bike ride, helmet and bike safety checks, kids’ activities and a live DJ.
Find deals at Mountain View‘s Citywide Garage Sale Sept. 14-15.
The Four Seasons Hotel Silicon Valley hosts the Terry Fox Run at Baylands Athletic Center in Palo Alto on Sept. 15 (check website for registration fee info). The 5K and 10K run and walk raises funds for cancer research.
The inaugural Bark in the Park in San Mateo on Sept. 15 will include a pup parade, games, contests and more.
The Palo Alto Weekly Moonlight Run & Walk returns for its 40th anniversary event Sept. 20 at the Palo Alto Baylands (registration is $44-$65 a person, early-bird pricing ends Aug. 31). The family-friendly race includes 5K and 10K runs, a half-marathon and a 5K walk.
The Downtown Wine Stroll returns to Los Altos Sept. 20, featuring 20 wineries at 23 tasting sites with chocolate samples to pair with your wine (early bird tickets $53.24). Bands will perform throughout downtown.
The 40th annual Coastal Cleanup Day Sept. 21 is an opportunity to support your favorite beaches, creeks, parks and neighborhoods. There are more than 30 group cleanups to join throughout San Mateo County, and self-led neighborhood cleanups are also encouraged through the month of September. Check the website for a complete schedule. For Santa Clara County Parks cleanups, click here.
Orchard Days at Filoli in Woodside run Sept. 21-Oct. 27. Take a self-guided orchard walk, grab a drink or bite to eat, pose for fall photos and stick around for family storytime and live music. (Orchard Days are included with all admission on the weekends of Sept. 21-Oct. 27 plus Oct. 14. Admission is $38 for adults, $36 for seniors 65 and up, $34 for students, teachers and military members, $28 for kids 5-17 years old and free for kids under 5.)
The city of Cupertino hosts its annual Citywide Garage Sale Sept. 28-29.
The HEAL Project Farm in Half Moon Bay hosts Roots & Watts Sept. 28 for elementary and middle school-aged kids and their caretakers with activity stations, a farm tour and produce samples.
Friends of Stevens Creek Trail hosts its 30th annual Trailblazer Race in Mountain View Sept. 29 with a ’90s throwback theme ($35-$45 registration fee, early-bird pricing ends Aug. 31). The race starts and ends on Stevens Creek Trail and goes into the Shoreline Park area, and there are 5K and 10K routes as well as kids’ races. All participants receive an event T-shirt, refreshments and a prize draw ticket.
Palo Alto Airport Day on Sept. 29 will include aircraft flyovers, air traffic control tower tours, airplane and helicopter displays, food trucks, a bounce house for kids and a flying car.
Movie nights and summer concert series
Sunnyvale‘s Sunset Movie Series concludes with “Elemental” Sept. 6.
Burlingame Parks and Recreation wraps up Movies in the Park with “Sing” Sept. 6 and “Up” Sept. 20.
Movies in the Park in San Mateo features “The Marvels” Sept. 6, “Trolls Band Together” Sept. 13, “The Parent Trap” Sept. 20 and “Elemental” Sept. 27. Arrive early for family-friendly games and activities.
Hillsdale Shopping Center’s Rock the Block concert series in San Mateo is on select Fridays throughout September. Catch Taylor Swift tribute band Twist on Taylor Sept. 6, ABC7 news anchor Dan Ashley and his Americana rock band Sept. 13 and ’90s rock cover band Fire Peach Sept. 20.
Mountain View‘s Concerts on the Plaza Friday night music series concludes this month with Bee Gees tribute band You Should Be Dancing Sept. 6; Mercy and the Heartbeats (’70s and ’80s classics and ’90s singalongs) Sept. 13; Native Elements playing roots reggae Sept. 20; and psychedelic Latin dance music artist Cumbia Paradiso Sept. 27.
Main Street Cupertino‘s annual summer concert series Live on Main wraps up this month with big band soul and R&B artist Noah & The Arkiteks Sept. 6, Motown and old school soul band Dolce Grande featuring Ren Geisick Sept. 13, party music band Cocktail Monkeys Sept. 20 and ’80s tribute band Flock of Seagirls Sept. 27.
Rock the Dock at the Port of Redwood City features rock and blues musicians Penetrator Groove Band Sept. 7, classic rock band Dutch Uncle Sept. 14, Pride and Joy SF playing pop, soul and Motown music Sept. 21, and The Deep Fakes with rock, dance and ’90s tunes Sept. 28.
Head to Memorial Park in Loma Mar Sept. 14 for Movie Night in the Redwoods featuring “Harry Potter and the Sorcerer’s Stone” (vehicle entrance fee $6).
Belmont‘s Movies in the Parks 2024 summer series continues with “Matilda” Sept. 20.
