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June is jam-packed with festivals and fairs to kick off a summer outdoors. From the annual San Mateo County Fair to events for Pride Month, Juneteenth and the World Cup (check back for a complete watch party guide the week of June 8), here are some of the biggest happenings in Silicon Valley this month.
The San Mateo County Fair is back with the Bayside 101 Music Festival, rides, carnival foods, exhibits and special events, including Family Pride Day June 6, Day of the Lion June 7, Kids Free Day June 12 (for children 12 and under) and more.
June 5, 4-10 p.m., and June 6-14, 11 a.m. to 10 p.m. (closed June 8-9), 1346 Saratoga Drive, San Mateo. Admission is $8-$23; children 5 and under get in free. Seniors 62 and over get in free June 11; kids 12 and under are free June 12. Parking passes, ride wristbands and music festival admission bundles are priced separately. sanmateocountyfair.com.
Score deals and reduce waste at the Palo Alto Citywide Yard Sale June 6.
June 6, 8 a.m. to 2 p.m., Palo Alto. paloalto.gov/Events-Directory/Public-Works/Citywide-Yard-Sale. Admission is free.
The Sunnyvale Art and Wine Festival celebrates its milestone 50th anniversary with live music, food and drinks, a kids’ zone and over 200 artists and makers.
June 6, 11 a.m. to 7 p.m. and June 7, 10 a.m. to 5 p.m., downtown Sunnyvale. Admission is free. sunnyvaleartandwine.com.
The La Honda Art & Music Fair, an annual benefit for the La Honda Educational Foundation, returns this weekend with a stacked lineup of local musicians, plus arts and crafts, a raffle, a children’s play area and food from Alice’s Restaurant.
June 6-7, 10 a.m. to 6 p.m., La Honda Gardens, 8865 La Honda Road, La Honda. visithalfmoonbay.org/events/la-honda-art-music-fair. Admission is free.
Pacifica Pride weekend kicks off Friday with free car decorating at Thistle & Tonic and Sharp Park Taproom in Pacifica plus a Pride panel in Half Moon Bay before the main event Saturday. Half Moon Bay Pride follows next weekend.
June 6, 11 a.m. to 3 p.m., Ingrid B. Lacy Middle School, 1427 Palmetto Ave., Pacifica, and June 14, 11:30 a.m. to 3:30 p.m., Mac Dutra Plaza, 504 Main St., Half Moon Bay. Free. instagram.com/p/DZFyteVgYhI/?img_index=1.
Hillsdale Shopping Center in San Mateo celebrates the World Cup coming to the Bay Area with kid-friendly soccer activities, a 10-foot soccer ball for photo ops, vintage soccer jerseys for sale and giveaways.
June 6, 11 a.m. to 2:30 p.m., North Block Plaza, 60 31st Ave., San Mateo. Free. hillsdale.com/events/hillsdale-shopping-center-world-cup-event.
Jazz on the Hill at College of San Mateo celebrates its 20th year with a full day of free live jazz outdoors June 6. Performers will include the Stanford Jazz Combo, Roger Glenn Latin Jazz Ensemble with special guest Ray Obiedo, SF Jazz High School Allstars and more. Food trucks and craft booths will also have goods available for purchase.
June 6, 11 a.m. to 6 p.m., College of San Mateo Library and Theatre (outdoors), 1700 W. Hillsdale Blvd., San Mateo. Free. collegeofsanmateo.edu/jazzonthehill.
The inaugural Palo Alto Pride will include dancing, singing, poetry and community speakers.
June 7, 2-5 p.m., King Plaza, 250 Hamilton Ave., Palo Alto. Free. paloalto.gov/Events-Directory/Community-Services/Palo-Alto-Pride.
The Biggest Little Air Show returns to Hiller Aviation Museum in San Carlos for a day of radio-controlled airplane demonstrations and displays. Performers will include the Sukhoi West Demo Team, United States Coast Guard Helicopter Search and Rescue and RC Flyers model aircraft.
June 13, 10:30 a.m. to 1 p.m., 601 Skyway Road, San Carlos. General admission is $18.93-$27.37 each; free admission for kids 3 and under. Sales end June 12 or when tickets are sold out. hiller.org/event/biggest-little-air-show.
Taste of Mountain View, a food, beer and wine walk on Castro Street, is back with bites from downtown restaurants paired with wine and live music.
June 17, 4-8 p.m., Castro Street, Mountain View. General admission is $81.88; food-only tickets are $55.20. Two- and four-ticket combos are also available. eventbrite.com/e/taste-of-mountain-view-food-beer-wine-walk-on-castro-street-tickets-1985860101020?aff=oddtdtcreator.
Menlo Park’s Juneteenth celebration will include storytelling and Caribbean music by Asheba along with performances by Menlo Park Soul Line Dancer and Myke tha Kidd. There will also be food for purchase, free treats and family-friendly activities.
June 19, 5-8 p.m., Belle Haven Community Campus, 100 Terminal Ave., Menlo Park. Free. menlopark.gov/Citywide-calendar/Community-events/20260619-Juneteenth-Celebration-observed.
Ube Festival Bay Area returns to the Cow Palace in Daly City for a day of Filipino food vendors showcasing the purple yam in sweet and savory foods and beverages, plus live music, traditional cultural performances and local makers.
June 20, 10 a.m. to 6 p.m., 2600 Geneva Ave., Daly City. Early-bird admission is $6.50; kids 5 and under get in free. cowpalace.eventhub.net/e/ube-fest.
The Juneteenth Community Festival in Los Altos will include music, dancing, art, performances, food and drinks, plus Black-owned small businesses selling hand-crafted goods.
June 20, 11:30 a.m. to 5 p.m., 97 Hillview Ave., Los Altos. Free. eventbrite.com/e/7th-annual-juneteenth-community-festival-tickets-1901805654909.
The 2026 Stanford Jazz Festival kicks off June 21 with 25 concerts featuring Luciana Souza, Anat Cohen, Stefon Harris and more. Tickets are on sale now, and a couple of concerts have already sold out.
Select dates June 21-July 31, times and venues vary. Tickets are $12-$100 each. stanfordjazz.org.
Silicon Valley Bicycle Coalition hosts the “World Kit” Caravan Ride around Sunnyvale at the end of June. Wear your favorite soccer team’s jersey on this bike ride by some of the best parks and soccer pitches in the city.
June 27, 10 a.m. to noon, starts at the Sunnyvale Caltrain station, 121 W. Evelyn Ave., Sunnyvale. Free. bikesiliconvalley.org/events.
Bark n’ Brewfest, a dog-friendly beer-tasting benefit for the Peninsula Humane Society & SPCA in Burlingame, will feature local craft breweries and artisan wineries pouring 3-ounce samples into a commemorative glass. There will also be an adoption booth and food from Sunset 29 BBQ for sale.
June 27, 2-5 p.m., West Washington Park, 850 Burlingame Ave., Burlingame. $60 each, $70 at the door or online June 27. phs-spca.org/beer.
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