September brings fall to our doorstep while summerlike weather persists, making it prime time for festivals, movie nights, outdoor dining and recreation. The calendar is bursting with opportunities to do all that and more with a wide variety of annual events and inaugural ones slated for this month. (In fact, there are so many events that you’ll find a separate guide to Oktoberfest, which takes place throughout September and October, here.)
From cultural events like Fiestas Patrias and Festa Italiana to numerous art festivals, curated food and drink events, and movies under the stars, here’s how to spend September in Silicon Valley. Admission to events is free unless otherwise noted.
Festivals, fairs and celebrations
Mountain View Art & Wine Festival: One of the biggest art and wine festivals on the Peninsula, it features over 400 artists and makers, live music, curated food and wine tastings, a kids’ zone, a sports lounge with a giant LED screen and a community talent stage.
Sept. 6 from 11 a.m. to 7 p.m. and Sept. 7 from 10 a.m. to 6 p.m. on Castro Street from El Camino Real to Evelyn Avenue, downtown Mountain View. mvartwine.com.
Santa Clara Art & Wine Festival: Santa Clara’s annual event features over 150 artists and craft vendors, a Kids Kingdom, live entertainment on two stages, food, wine and beer.
Sept. 13, 10 a.m. to 6 p.m. and Sept. 14, 10 a.m. to 5 p.m. at Central Park, 909 Kiely Blvd., Santa Clara. santaclaraca.gov/our-city/departments-g-z/parks-recreation/parks-recreation-special-events/art-wine-festival.
Harvest History Festival, Mountain View: Celebrate the city’s rich agricultural history at a family-friendly event featuring live music by The Stragglyrs, garden demonstrations and a look at the historic Immigrant House. Children’s activities include bubble entertainment, a puppet show, caricatures, art projects and face painting.
Sept. 13, 9 a.m. to noon at Heritage Park, 771 N. Rengstorff Ave., Mountain View. Street parking is very limited, and attendees should plan to bike or walk to the event. mountainview.gov/our-city/departments/community-services/special-events/harvest-history-festival.
Fiestas Patrias, Redwood City: The event celebrating Latin countries and Mexican independence is back in downtown Redwood City Sept. 14 with authentic Mexican food, arts and crafts vendors, Ballet Folklorico dancing, live Mariachi music, a traditional flag ceremony and a kids’ area.
Sept. 14, 2-8 p.m. at Courthouse Square, 2200 Broadway, downtown Redwood City. redwoodcity.org/residents/redwood-city-events/cultural/fiestas-patrias.
Festa Italiana, South San Francisco: Find Italian food, a kids’ zone, a car show, a bocce tournament, vendors, live music and an Italian American cinema exhibit at Orange Memorial Park in South City Sept. 14.
Sept. 14, 11 a.m. to 6 p.m. at Orange Memorial Park, Orange Avenue and Tennis Drive, South San Francisco. cacolumbia.wordpress.com/festa-italiana-2023-ssf.
Los Gatos Art & Wine Festival: The town’s annual event will have live music all weekend, fine wine and craft beer, gourmet food trucks and over 200 artists selling their wares.
Sept. 20-21, 10 a.m. to 6:30 p.m. on the Civic Center lawn, 110 E. Main St., Los Gatos. losgatosfiesta.com.
Art & Lit Fest, Daly City: This event showcasing local poets, artists, musicians, authors and crafters is returning to Daly City at the end of the month. It will include an art gallery, children’s activities, a beat-making workshop, artisan vendors, and live music and performances.
Sept. 27, 11 a.m. to 3 p.m. at Serramonte Center, 3 Serramonte Center, Daly City. dcpla.org/artfest-about.
Great Glass Pumpkin Patch, Palo Alto: More than 25 artists handcraft over 10,000 glass pumpkins in all sizes and colors for this popular fall event. A percentage of sales benefit the Bay Area Glass Institute and the Palo Alto Art Center Foundation.
Sept. 27-28, 10 a.m. to 5 p.m. at the Palo Alto Art Center, 1313 Newell Road, Palo Alto. greatglasspumpkinpatch.org.
Fog Fest, Pacifica: This Coastside celebration includes a Saturday morning parade, the Fall Family Fun Fest Sunday, a photo contest and the Fog Jog along with two days of arts and crafts vendors, live music, food and drinks.
Sept. 27-28, 10 a.m. to 6 p.m. on Palmetto Avenue, Pacifica. pacificcoastfogfest.com.
Millbrae Mid-Autumn Festival: Celebrate the Chinese tradition with live performances and entertainment, food, family-friendly activities and artisans in downtown Millbrae.
Sept. 27, 10 a.m. to 7 p.m. and Sept. 28, 10 a.m. to 5 p.m. at 200-400 Broadway, downtown Millbrae.
Airport Day, Palo Alto: The Palo Alto Airport opens for a free community event featuring helicopters, gyroplanes and real display aircraft; information on learning to fly and the science of flight; and food trucks. Biking to the event is encouraged, and a free bike corral will be monitored by volunteers from the Silicon Valley Bicycle Coalition.
Sept. 28, 10 a.m. to 2 p.m. at the Palo Alto Airport, 1925 Embarcadero Road, Palo Alto. paloaltoairport.org/airport-day.
September Arts & Culture Fest, San Mateo: Head to downtown San Mateo for a festival featuring local musicians, cultural performances, artists and makers, family-friendly activities, food, wine and beer.
Sept. 28, 11 a.m. to 5 p.m. on B Street between 1st and 3rd avenues plus Baldwin Avenue, San Mateo. sanmateochamber.org/sept-fest.
Food and drink events
Pub in the Park, Redwood City: The summer series concludes with music from contemporary bluegrass band Savannah Blu. Participating food trucks include MoBowl, Los Tolucas, Sam’s Chowder House, Waffle Roost and Humphry Slocombe. Grab beer, cider and seltzer from local breweries, including Blue Oak Brewing Company, Ghostwood, Alpha Acid Brewing Company and more.
Sept. 6, 11 a.m. to 4 p.m. at Red Morton Park, 1120 Roosevelt Ave., Redwood City. redwoodcity.org/residents/redwood-city-events/pub-in-the-park-4124.
San Mateo Consolidated Firefighters Association Chili Cook-Off, San Mateo: The annual chili cook-off returns to Central Park, where a $15 entry fee at the gate includes tastings of every chili available, a full bowl and a drink ticket good for a beer, seltzer or water. Additional drink tickets can be purchased inside. Bring a blanket or lawn chairs and stick around for live music from SIX50 Productions and a jump house for kids.
Sept. 6, 11 a.m. to 4 p.m. at Central Park, 50 E. 5th Ave., San Mateo. Admission is $15; additional drink tickets are $1 per water, $5 per beer or seltzer. dsma.org/event/san-mateo-firefighters-associations-chili-cook-off-at-central-park.
Taste of Los Gatos: The downtown street festival features live music, a family fun zone, a craft beer tap truck, a shaded relaxation space and a Porsche car show. Buy a tasting wristband to try bites from 27 Los Gatos restaurants and 1-ounce pours from 20 local wineries.
Sept. 6, noon to 5 p.m. (doors open at 11:30 a.m.) in downtown Los Gatos. Admission is free, but tickets for bites are $80.12 each ($100 day of); bites and libations tickets are $101.22 each ($120 day of). eventbrite.com/e/taste-of-los-gatos-tickets-1395229341519.
Downtown Los Altos Whiskey & Bites Stroll: Sample bites from Los Altos restaurants and whiskey from a wide range of distilleries at this inaugural event. Tickets also include a collectible souvenir glass and a map to tasting sites.
Sept. 12, 6-9 p.m. in downtown Los Altos (check-in starts at 5 p.m. in Veterans Community Plaza, Main and State streets). This event is 21 and over. Tickets are $83.53 each ($89.36 day of) or $118.46 for a regular ticket plus a bites-only ticket. eventbrite.com/e/2025-downtown-los-altos-whiskey-bites-stroll-tickets-1123221609069.
Salsa Competition, Redwood City: San Mateo County Parks is hosting its annual salsa competition and partnering with other agencies to provide community resources and activities at the event. A dance performance by Danza Colibri is set for 5:30 p.m.
Sept. 12, 4:30-6:30 p.m. at Friendship Park, 290 Huntington Ave., Redwood City. instagram.com/smcparks.
Fall Wine Walk, Campbell: Try wines from more than 25 winemakers at the 16th annual event. Each ticket includes a commemorative tasting tumbler good for one pour at each tasting location. Designated drivers do not need a ticket.
Sept. 18, 6-9 p.m. in downtown Campbell. downtowncampbell.com/winewalk. Tickets are $55.20 each; prices increase Sept. 15.
Chili Cook-Off, Colma: Molloy’s Tavern is hosting a chili cook-off with tastings, a prize drawing, music and food. Sign up to enter your chili at the bar.
Sept. 20, tastings begin at 3 p.m., winners announced at 4:30 p.m. at Molloy’s Tavern, 1655 Old Mission Road, Colma. instagram.com/molloyscolma.
Woodside-Portola Valley Fire Protection Foundation Chili Cook-Off & BBQ, Woodside: This special event will feature kids’ firefighter games, self-guided sculpture farm tours, an auction, music, barbecue and a chili contest hosted and judged by Woodside firefighters.
Sept. 28, 3-7 p.m. at Runnymede Sculpture Farm, 980 Runnymede, Woodside. Tickets are $75 for adults, $35 for kids 5-12 and free for kids 4 and under. No tickets will be sold at the event. eventbrite.com/e/woodside-fire-foundations-chili-cook-off-bbq-tickets-1539033112469?aff=oddtdtcreator.
Movie nights
Movies in the Park, San Mateo: The four-night movie series will be held at San Mateo parks Friday nights throughout September starting with “Shrek” at Central Park Sept. 5; “Despicable Me 4” at Dr. MLK Jr. Park Sept. 12; “Inside Out 2” at Bay Meadows Park Sept. 19; and “Moana 2” at Beresford Park Sept. 26. Food and drinks will be available for purchase, and family-friendly games and activities will start at 6 p.m. Bring blankets and chairs.
Sept. 5 at Fitzgerald Field, Central Park, 50 E. 5th Ave.; Sept. 12 at Dr. MLK Jr. Park, 725 Monte Diablo Ave., San Mateo; Sept. 19 at Bay Meadows Park, 301 E. 28th Ave., San Mateo; and Sept. 26 at Beresford Park, 2720 Alameda de las Pulgas. Movies start between 7:30-7:45 p.m. cityofsanmateo.org/3244/Movies-in-the-Park.
Outdoor Movie Night, Foster City: Watch “Wicked” at the Leo J. Ryan Park amphitheater. Come early for concessions and lawn games.
Sept. 12, movie starts at 7:30 p.m. at Leo J. Ryan Park, 650 Shell Blvd., Foster City. fostercity.org/community/page/outdoor-movie-night-wicked.
Movies in the Park, Burlingame: Burlingame Parks and Recreation’s Friday night summer movie series concludes with “Inside Out 2” on Sept. 12. The movie starts at sunset; blankets and low-back chairs are encouraged.
Sept. 12, movie starts at sunset at Washington Park, 850 Burlingame Ave., Burlingame. burlingame.org/1123/Movies-in-the-Park.
Millbrae Goes to the Movies: Catch a sunset screening of “Dog Man” at Millbrae’s Central Park.
Sept. 12, movie starts at sunset at Central Park, 477 Lincoln Circle, Millbrae. ci.millbrae.ca.us/Calendar.aspx?EID=1488.
Movies in the Park, Belmont: Watch “Mulan” at Alexander Park and come early to save your spot with blankets or camping chairs. Come early to buy snacks, play games and participate in a raffle for prizes from local businesses.
Sept. 12, movie starts at sunset at Alexander Park, 400 block of Yorkshire Way, Belmont. belmont.gov/Home/Components/Calendar/Event/8386/559?backlist=%2fdepartments%2fparks-and-recreation.
Cinema at the Cemetery, Colma: The town of Colma is hosting a screening of “The Goonies” at the Italian Cemetery Mausoleum. Food and drink is permitted except for glass. A second screening featuring “The Haunted Mansion” is scheduled for October.
Sept. 27, movie starts at dusk at the Italian Cemetery, 540 F St., Colma. Early arrival is recommended due to limited space; admission starts at 6 p.m. instagram.com/colmarecreationservices.
Outdoor recreation
Tour de Menlo, Menlo Park: Cyclists can choose from one of four routes for riders of all abilities, including a new 12-mile family route. Other routes are 33, 43 and 65 miles. All routes are well-marked and include refreshments and restrooms at rest stops along the way before cyclists return to The Church of Jesus Christ of Latter-day Saints for lunch in the courtyard. Proceeds benefit the Menlo Rotary Community Foundation for need-based college scholarships.
Sept. 13, 65-mile route starts at 7 a.m., 43-mile route starts at 8 a.m., 33-mile route starts at 9 a.m. and the 12-mile family ride begins at 10 a.m. Rides start and end at The Church of Jesus Christ of Latter-day Saints, 1105 Valparaiso Ave., Menlo Park. Registration is $90 for adults, $30 for youth 17 and under. tourdemenlo.com.
Terry Fox Run, Palo Alto: Four Seasons Hotel Silicon Valley is hosting the annual 5K and 10K run and walk for cancer research at Baylands Athletic Center. After completing the run, participants can grab a bite to eat from the Four Seasons food truck.
Sept. 14, registration at 9:30 a.m., run/walk 10 a.m. to 2 p.m. at Baylands Athletic Center, 1900 Geng Road, Palo Alto. Check website for registration cost. tinyurl.com/terryfoxrunsiliconvalley.
Portola Valley Town Picnic & Zott’s to Tots: A family fun run and bike ride kicks off the day, followed by the town picnic featuring live music, barbecue, a taco truck and kids’ activities, including a petting zoo, jump houses and more.
Sept. 20, fun run starts at 10 a.m. at Rossotti’s Alpine Inn, 3915 Alpine Road, Portola Valley; picnic from 11 a.m. to 1 p.m. at the Portola Valley Town Center, 765 Portola Road. Fun run preregistration required before noon on Sept. 19. portolavalley.net/community/town-sponsored-events/zott-s-to-tots.
Community Bike Ride, Foster City: Participants will take a 5- or 10-mile ride around the city and receive giveaways, including free refreshments. No registration is required.
Sept. 21, 10:30 a.m. at Boothbay Park, Boothbay Avenue and Edgewater Boulevard, Foster City. fostercity.org/community/page/join-community-bike-ride-september-21.
Belmont Water Dog Run: The event features a 10K, a 5K, a 1-mile kids’ race and a 1-mile “Fido race” for dog owners and their four-legged friends (bandana swag included). The morning kicks off with a pancake breakfast at the Twin Pines Senior Center and concludes with an awards ceremony. Same-day registration will be accepted.
Sept. 27, 10K race starts at 7:15 a.m., 5K at 7:30 a.m., 1-mile kids’ race at 8:45 a.m. and Fido race at 9:15 a.m. Race expo runs from 6:30-10:30 a.m. The event starts at Twin Pines Park, 1 Twin Pines Lane, Belmont. Registration is $54.42 for the 5K, $65.11 for the 10K, $23.39 for the kids’ run and $23.39 for the Fido Mile. Additional costs apply for parent escorts at the kids’ race or additional Fido Mile escorts. belmontwaterdogrun.com.
Trailblazer Race, Mountain View: The 31st annual race includes family-friendly 10K, 5K and kids’ races on flat, shaded running courses on Stevens Creek Trail and at Shoreline. A 3-mile walking course is also offered. There will be free kids’ activities and a festival area with snacks, exhibits and prize drawings. Participants will receive a custom event T-shirt, a medal, refreshments and a prize drawing ticket. Proceeds benefit the Friends of Stevens Creek Trail.
Sept. 28, 8:30 a.m. (check-in and day-of registration starts at 7:30 a.m.) at the Microsoft Silicon Valley Campus, 1045 La Avenida St., Mountain View. Registration is $44.15-$60.05. trailblazer.itsyourrace.com/event.aspx?id=6293.
Citywide Garage Sale, Mountain View: Hundreds of residents will host garage sales at their homes during this two-day event. Check the online map for directions and searchable filters, or go online for a list of addresses and sale items.
Sept. 13-14 in Mountain View. mountainview.gov/garagesale.
Citywide Garage Sale, Cupertino: Cupertino residents can register until Sept. 12 to host a garage sale Sept. 20-21. An online garage sale map and list will be posted on the city’s website, and a limited number of printed maps and lists will be available Sept. 16 at the Cupertino Library, Quinlan Community Center and Cupertino Senior Center.
Sept. 20-21, 9 a.m. to 4 p.m. in Cupertino. cupertino.gov/garagesale.
Head West Marketplace, San Mateo and Los Altos: Head West Marketplace features local small businesses selling various goods, from handmade jewelry to vintage wares. Find it in downtown San Mateo every third Sunday through December and every fourth Sunday through October in downtown Los Altos (weather permitting).
Sept. 21 and Sept. 28, 11 a.m.-5 p.m. on South B Street, 1st Avenue to 3rd Avenue, San Mateo. headwestmarketplace.com/southbstreet. July 27 and Aug. 24, 11 a.m.-5 p.m. on State Street at 3rd Street, Los Altos. headwestmarketplace.com/statestreet.
Concert series
Rock the Block, San Mateo: Hillsdale Shopping Center’s third annual Rock the Block concert series returns with singer and songwriter Mike Annuzzi Sept. 5, an artist to be announced Sept. 12, six-piece band Top Concert Sept. 19 and musician NiNi Sept. 26.
Fridays through Sept. 26, 6-8 p.m. at Hillsdale Shopping Center (outdoor north block plaza), 60 31st Ave., San Mateo. hillsdale.com/events.
Concerts on the Plaza, Mountain View: Mountain View’s summer concert series concludes with The Peelers (latest hits cover/mashup band) Sept. 5, Fog City Swampers (CCR/rock) Sept. 12, The Wanderers (classic/modern dance rock) Sept. 19 and The Drifting Cowboys (Hank Williams tribute band) Sept. 26.
Fridays through Sept. 26, 6-7:30 p.m. at Civic Center Plaza, 500 Castro St., Mountain View. mountainview.gov/our-city/departments/community-services/special-events/concerts-on-the-plaza.
Rock the Dock, Redwood City:
Saturdays, 3:30-6:30 p.m. at the Port of Redwood City, 459 Seaport Court, Redwood City. $5-$20 suggested donation. rockthedockrwc.com.
Beats, Brews and Vines, Millbrae: Mambo Street is performing next at Millbrae’s summer concert series.
Sept. 18, 6-8 p.m. on Broadway in downtown Millbrae. ci.millbrae.ca.us/354/Beats-Brews-Vines.
Summer Nights, San Carlos: Devil’s Canyon Brewing Company hosts the final night of its summer concert series with an Around the World Night celebrating global cultures. Check their website for forthcoming details on the event.
Sept. 26, 4-10 p.m. at Devil’s Canyon Brewing Company, 935 Washington St., San Carlos. devilscanyon.com/summer-nights-2025.html.
