Labor Day Weekend (Aug 29–Sep 1, 2025)
Burlingame Movies in the Park (Free) – Fri Aug 29, sunset at Washington Park baseball field. Bring blankets and low chairs. Great family vibe.
Belmont Greek Festival (Holy Cross Church) – live music/dance, kids’ entertainment, plenty of food; a Peninsula Labor Day staple. Noon-10 p.m. Saturday-Sunday, Aug. 30-31. $3-$5; under 13 free. Holy Cross Church, 900 Alameda de las Pulgas, Belmont.
Kings Mountain Art Fair For its 62nd year, the annual festival is set to include works from more than 140 artists, food and drinks vendors and a children’s area. Proceeds support the Kings Mountain volunteer fire brigade and elementary school. 10 a.m.-5 p.m. Saturday-Monday, Aug. 30-Sept. 1. Free admission. Kings Mountain Community Center, 13889 Skyline Blvd., Woodside.
Millbrae Art and Wine Festival Downtown Millbrae will transform into a large street fair with seven blocks of artisan vendors, food trucks, live music, a youth fun zone, classic car show and more. 10 a.m.-5 p.m. Saturday-Sunday, Aug. 30-31. Free admission. Broadway, between 200 Victoria Ave. and 979 Broadway/Meadow Glen Ave., downtown Millbrae.
September 2025
San Mateo
Movies in the Park (Free) – Every Friday in September at Central Park (family films at dusk). (City of San Mateo, Facebook)
September Nights on B Street (Free) – Thu Sep 11 & Thu Sep 18, 6–8 pm: live music + street fun downtown. (City of San Mateo)
SM Firefighters’ Chili Cook-Off – Sat Sep 6, 11 am–4 pm at Central Park; food, music, kids’ zone. (Downtown San Mateo)
Bike Rodeo (Family skills ride) – Fri Sep 26, 5–6:30 pm at Beresford Park. (City of San Mateo)
San Mateo Certified Farmers’ Market (Year-round) – Saturdays 9 am–1 pm at College of San Mateo—easy family outing. (PCFMA)
Burlingame
Family Campout (Washington Park) – Fri–Sat Sep 12–13 (BBQ dinner, games, outdoor movie, pancake breakfast). (Burlingame)
Movies in the Park (Free) – Fri Sep 12 at Washington Park baseball field (movies start at sunset). (The San Francisco Peninsula)
Library Family Storytime (Free, indoors) – Ongoing; check Thu Sep 18 10:30–11:00 am Lane Room (good toddler option). (Burlingame)
San Carlos
HarringTunes (Music + chess afternoon, family-friendly) – Sun Sep 7 & Thu Sep 25 at Frank D. Harrington Park. (City of San Carlos)
Belmont
Belmont Greek Festival (repeat if you missed it Labor Day weekend) – details above. (BELMONT GREEK FESTIVAL)
Belmont Water Dog Run (5K/10K/1-Mile) – Sat Sep 27 at Twin Pines; kids welcome (great community morning). (Race Roster)
Redwood City
Fiestas Patrias (Free) – Sun Sep 14, 2–8 pm at Courthouse Square; family celebration of Latin American cultures with music, dance, food. (Redwood City, EventHub)
Oktoberfest Downtown (Ticketed; family day seatings available) – Sep 19–28 (no event Mon Sep 22) in the Courthouse Square festival tent. (Redwood City)
Pub in the Park – Sat Sep 6, 11 am–4 pm at Red Morton Park; lawn games, music, relaxed family hangout. (Redwood City, Funcheap)
Foster City
Community Bike Ride (Free) – Sun Sep 21, 10:30 am from Boothbay Park; 5- or 10-mile routes with refreshments. (Foster City)
Off the Grid: Foster City (Food-truck night) – Wed Sep 3 (and most Wednesdays) 5–9 pm on Shell Blvd—easy dinner + park time with kids. (Capelo's Barbecue