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Whether you consider Memorial Day weekend or the solstice to be the start of summertime, get in the spirit of the season with traditional festivities like art and music festivals, the San Mateo County Fair, outdoor movie nights and more.
Here’s our running guide to Peninsula events through the rest of May and June. Check back at the end of May for a separate Pride Month events roundup. Events are free unless otherwise noted.
San Mateo County Fair, San Mateo: The county fair returns with the Bayside 101 Music Festival May 30-31 with performances by Better Than Ezra, Everclear, Hoobastank and more. Drone shows will also be held at 9:15 p.m. on festival days. The fair continues with more concerts, carnival food and rides, exhibits and much more.
May 30, 4-10 p.m.; May 31, June 1 & 4-8, 11 a.m. to 10 p.m. at the San Mateo Event Center, 1346 Saratoga Drive, San Mateo. Admission and ride prices vary; parking is $18 for credit cards, $20 cash. sanmateocountyfair.com.
Music on the Square 2025, Redwood City: The Friday night summer music series returns with Santana tribute Carnaval! May 30; Groove Ride playing dance favorites June 6; Neon Velvet playing modern rock dance hits June 13; cumbia and world music band La Gente SF June 20; and Foreigner Unauthorized June 27. A pre-show party will be held from 4-6 p.m. May 30 with bites from downtown restaurants, a cash bar and live music by Sound Union; a $25 donation is suggested at the door. A separate Classical on the Square event with Redwood Symphony is scheduled for June 21.
Fridays May 30 through Aug. 29, 6-8 p.m. (Classical on the Square is June 21, 7 p.m.) at Courthouse Square, 2200 Broadway, Redwood City. redwoodcity.org/residents/redwood-city-events/music/music-on-the-square.
PV Palooza Summer Music Festival: The free all-day music festival features 20 local bands on three stages (including a showcase stage for youth acts and smaller bands), local art exhibitors and kids’ activities. Food, wine and beer will also be available for purchase.
May 31, 10:30 a.m. to 8:30 p.m. at the Portola Valley Town Center, 765 Portola Road, Portola Valley. pvpalooza.com.
Pub in the Park, Redwood City: Red Morton Park will host four monthly Saturday events through September with inflatable pubs selling craft beer and cider, food trucks and live bluegrass music. Wildcat Mountain Ramblers will kick off the series.
May 31, 11 a.m. to 4 p.m. at Red Morton Park, 1455 Madison Ave., Redwood City. redwoodcity.org/residents/redwood-city-events/music/pub-in-the-park.
Movies on the Square 2025, Redwood City: Catch free movies for all ages every Thursday for 12 weeks beginning June 5 with “Twisters.” The rest of the month features “Mean Girls” (the musical, main feature) and “Despicable Me 4” June 12; a Juneteenth celebration and “Bob Marley: One Love” June 19; and “Dune Part 2” June 26. View the complete schedule online.
June 5, 8:30 p.m.; June 12 & 19, 6 p.m. kids’ feature and 8:30 p.m. main feature; June 26, 8:30 p.m. at Courthouse Square, 2200 Broadway, Redwood City. redwoodcity.org/residents/redwood-city-events/movies.
Summer Family Movie Night Series, Palo Alto: Bring blankets, lawn chairs and snacks and watch “Inside Out 2” June 6 and “Despicable Me 4” June 20 at Mitchell Park’s athletic fields. The movie night series runs through August; check online for the complete lineup.
June 6 and June 20, sunset (seating begins at 7 p.m.) at Mitchell Park athletic fields, 600 E. Meadow Drive, Palo Alto. paloalto.gov/Events-Directory/Community-Services/Family-Movie-Night-Series.
La Honda Fair: The annual music and art festival will feature local acts such as Banana Slug String Band, Pathetic Honey, Skalonda and more.
June 7-8, 11 a.m. to 6 p.m. outside La Honda Country Market, 8865 La Honda Road, La Honda. facebook.com/p/La-Honda-Fair-Music-Festival-100081783999718.
Children’s Day Celebration, Daly City: The Daly City Chinese Youth Committee hosts a day of performances, activities and family fun. Food will also be available on a first come, first served basis.
June 7, 11 a.m. to 2 p.m. at Gellert Park, 50 Wembley Drive, Daly City. instagram.com/dalycitygov.
Juneteenth Celebration, San Bruno: The cities of San Bruno and Millbrae are hosting this celebration, featuring live music, dancing, storytelling, crafts and lunch catered by Hip Hop BBQ Shack (while supplies last).
June 7, 11 a.m. to 3 p.m. at San Bruno City Park (near the gazebo), 251 City Park Way, San Bruno. sanbruno.ca.gov/873/Juneteenth.
Summer Puppetry Festival, Menlo Park: The Menlo Park Library kicks off its eighth annual festival with the authors of “A Century of California Puppetry: How the West was Strung” on June 9. On June 24, stop by for a screening of the documentary “I Am Big Bird: The Caroll Spinney Story.” And on June 29, The Puppet Company will tell the story of “The Sorcerer’s Apprentice” at the Belle Haven Library. The festival runs through August; go online for the full schedule.
June 9, 6-7 p.m. and June 24, 6-7:30 p.m. at the Menlo Park Library, 800 Alma St., Menlo Park; and June 29, 11-11:45 a.m. at the Belle Haven Library, 100 Terminal Ave., Menlo Park. menlopark.gov/Government/Departments/Library-and-Community-Services/Events.
Taste of Mountain View Food, Wine & Beer Walk: Enjoy bites and drinks from local businesses along with live music at this family-friendly event. Food-only tickets and tickets for food and drinks are available. Participants will receive swag bags plus event wine glasses for food and drink ticketholders.
June 11, 4-8 p.m. in downtown Mountain View. Food-only tickets are $44.52, food and drink tickets are $76.54. eventbrite.com/e/taste-of-mountain-view-food-beer-wine-walk-on-castro-street-tickets-1222379262279?aff=erelexpmlt.
Free Outdoor Movie Night, Foster City: “Moana 2” will be screened in the Leo J. Ryan Park meadow. Lawn games and concessions will be available until the movie starts. Attendees should bring chairs and blankets.
June 12, 7-10:30 p.m. (movie begins at 8:30 p.m.) at the Leo J. Ryan Park meadow, 650 Shell Blvd., Foster City. fostercity.org/parksrec/page/free-outdoor-movie-night.
Flick and Float, San Bruno: Watch “Moana 2” from a provided inflatable in the outdoor pool. Refreshments will be provided.
June 13, 7-9 p.m. at the Recreation & Aquatic Center, 251 City Park Way, San Bruno. $5 for RAC members, $10 for residents, $15 for nonresidents. Children under 14 must have an adult present. Register online at secure.rec1.com/CA/san-bruno-ca/catalog.
Biggest Little Air Show, San Carlos: The Sukhoi West Demo Team will headline the air show and be joined by demonstrations of radio-controlled model aircraft, including aerobatic helicopters, quadrotors, drones and more. Find the complete schedule of events online.
June 14, 10:30 a.m. to noon at Hiller Aviation Museum, 601 Skyway Road, San Carlos. Admission is $25 for adults, $17 for seniors 65 and up and youth 5-17, free for children 4 and under. Additional service fees apply. Tickets will not be sold at the door. hiller.org/event/biggest-little-air-show.
Juneteenth Community Festival, Los Altos: The sixth annual festival will include a family relay race, music and dancing, vendors, food and drinks, art and more.
June 14, 11:30 a.m. to 5 p.m. at the Los Altos Community Center, 97 Hillview Ave., Los Altos. eventbrite.com/e/6th-annual-juneteenth-community-festival-tickets-1145063077489.
Juneteenth Celebration, Menlo Park: Planned activities include live music and entertainment, family-friendly activities, a local tribute and a community basketball game for ages 13 and over. Food will also be available for purchase.
June 14, noon to 3 p.m. at Kelly Park, 100 Terminal Ave., Menlo Park. menlopark.gov/Citywide-calendar/Community-events/20250614-Juneteenth-Celebration-observed.
Dads & Dogs 2025 – Father’s Day Family Ride, Mountain View: Silicon Valley Bicycle Coalition is hosting a free group bike ride from Red Rock Coffee to Cuesta Park, where there will be therapy dogs, frisbee, soccer, hacky sack and bubbles. Meet at 9:30 a.m. for bike light giveaways, helmet fittings, light bike adjustments and snacks before the ride at 10 a.m.
June 15, 9:30 a.m. to noon. Meet at Red Rock Coffee, 201 Castro St., Mountain View. eventbrite.com/e/dads-dogs-2025-fathers-day-family-ride-tickets-1355598725279.
Music in the Park 2025, Redwood City: Stafford Park will host 10 weeks of live music every Wednesday starting June 18. Performances in June will include San Benito County Line (country) June 18 and Celtic rock band Tempest June 25. The Optimist Club of Redwood City will serve hot dogs, hamburgers, chips and drinks. All proceeds benefit the Save the Music program in Redwood City schools.
Wednesdays June 18-Aug. 20, 6-8 p.m. (5:30-7:30 p.m. starting Aug. 13) at Stafford Park (corner of King Street and Hopkins Avenue), Redwood City. redwoodcity.org/residents/redwood-city-events/music/music-in-the-park.
ART on the Square, Redwood City: Shop fine arts and crafts in downtown Redwood City with the first of four summer markets June 20. Cumbia and world music band La Gente SF will perform.
June 20, 5-8:30 p.m. on Hamilton Avenue at Courthouse Square, 2200 Broadway, Redwood City. artonthesquarerwc.com.
Summer Kick Off Movie Night, Colma: The Colma Community Center will host an all-ages viewing of “Barbie,” plus “Barbie”-themed activities and snacks. Attendees are encouraged to dress up in “Barbie”-inspired outfits.
June 20, 6-9 p.m. Children 13 and younger must be accompanied by an adult. Registration is encouraged at colma.ca.gov/event/summer-kick-off-movie-night-barbie.
Around the World, Sunnyvale: This new family-friendly event celebrating the region’s multiculturalism will feature live performances, food trucks and over 40 vendors.
June 21, 3-8 p.m. at Cityline Redwood Square (intersection of Murphy and W. McKinley avenues), Sunnyvale. eventbrite.com/e/around-the-world-in-collaboration-with-vibes-smiles-tickets-1320724104349.
Kids Rock!, Redwood City: The kid-centric music series returns for the summer with Andy Z and the Andyland Band June 28.
June 28, 10 a.m. to noon at Courthouse Square, 2200 Broadway, Redwood City. redwoodcity.org/residents/redwood-city-events/music/kids-rock.
Circus Bella: HOOPLA!, San Bruno: Circus Bella is stopping in San Bruno as part of its free Circus in the Parks series. The circus troupe includes acrobats, aerialists, jugglers and clowns. Audience members are invited to bring picnic blankets and small folding chairs, as seating isn’t provided. There will also be food vendors, face painters and balloon twisters. Midpeninsula residents, mark your calendars for the troupe’s July 4 show at Burgess Park in Menlo Park.
June 28, 11 a.m. and 1 p.m. (performances are 60 minutes) at San Bruno City Park, 251 City Park Way, San Bruno. Suggested donation $20. circusbella.org.
Bark n’ Brewfest, Burlingame: Bring your canine companions to this annual fundraiser for Peninsula Humane Society at West Washington Park. Ticket holders will receive unlimited 3-ounce pours of beer and cider in a commemorative glass. Participating breweries include Barebottle Brewing Company, Ghostwood, Laughing Monk Brewing and many more. There will also be treats for dogs plus food from Sunset 29 BBQ available for purchase.
June 28, 2-5 p.m. at West Washington Park, 850 Burlingame Ave., Burlingame. Tickets are $55.09 through May 26, $65.75 from May 27-June 27 and $76.41 online and at the door June 28. phs-spca.org/beer.
Sounds of the Shores 2025, Redwood Shores: Listen to music by the lagoon and grab a bite from a food truck as part of this special monthly summer concert series. The first concert will feature The Cocktail Monkeys (rock, R&B and soul music) plus food from Melina’s Kitchen.
June 28, 5-7 p.m. at Marlin Park, Neptune and Cringle drives, Redwood Shores. redwoodcity.org/residents/redwood-city-events/music/sounds-of-the-shores.
