Around the Peninsula
A running list of the community events I love in San Mateo County — the concerts, movie nights, and neighborhood gatherings that make this such a good place to live. Flyers below.
Browse City of San Mateo Activities →Friday, October 30, 2026 — 4:30 to 6:30 p.m. on 25th Avenue in San Mateo. Trunk set-up starts at 4 p.m., and participating businesses will decorate and pass out treats. Bring the family!
Friday, October 30, 2026 — 4:30 to 6:30 p.m.
25th Avenue, San Mateo
Save the date! Trunk set-up starts at 4 p.m. Participating businesses will decorate and pass out treats at this family-friendly Halloween event.
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Thursday, September 10 & Thursday, September 17
Downtown San Mateo — B Street, between 1st and 3rd avenues
Spend an evening with us on B Street, where live music, great food and family-friendly activities bring the block to life. Join the fun from 6–8 p.m.
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Fridays, September 11, 18 & 25, 2026
Shoreview, Laurie Meadows, and Beresford Parks
Upcoming free family movie nights hosted by City of San Mateo Parks & Recreation: How to Train Your Dragon (Sep 11), Lilo & Stitch (Sep 18), and Wicked: For Good (Sep 25).
View flyer ↓City of San Mateo Special Events →
Saturday, September 26 — 11 a.m. to 6 p.m.
B Street, Downtown San Mateo
A day of local art, live culture and community on B Street, hosted by the San Mateo Area Chamber of Commerce with Downtown San Mateo and the San Mateo County Arts Commission.
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