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June 2026
Jazz on the Hill
Date: Saturday, June 6, 2026
11:00 AM – 6:00 PM
Location: College of San Mateo
Event Page: https://collegeofsanmateo.edu/jazzonthehill/
Details: Jazz on the Hill is a free outdoor music festival at College of San Mateo featuring live jazz performances, local food vendors, community booths, and stunning Bay views. It's a long-running Peninsula tradition that brings together music lovers, families, and the local community for a fun summer day outdoors.
Why Families Will Love This:
• Free admission and free parking
• Open outdoor setting with plenty of space for kids and families
• Live music throughout the day without feeling crowded
• Food trucks, snacks, and local vendors on-site
• Bring a picnic blanket or lawn chair and spend the afternoon together
June 2026
San Mateo County Fair
Date: Sat May 30-Fri Jun 8 (closed Mon/Tue), 11AM-10PM daily
Location: 1346 Saratoga Dr, Event Center
Official Event Page: Fair Website
Details: Carnival rides, pig races, petting zoo at Event Center. Kids 12 & under FREE select days.
Why Families Will Love This:
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Kids 12 & under FREE Thu Jun 5
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Pig races + Creative Kids crafts
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Family Pride Day (Jun 6)
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Carnival rides all week
June 2026
Juneteenth Celebration
Date: Thursday Jun 18-19 (library events all day)
Location: County Library branches + city facilities closed Jun 19
Event Page: City Calendar
Details: Cultural storytimes, crafts, city holiday at County Libraries. Family learning + day off together.
Why Families Will Love This:
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Cultural storytimes + crafts for kids
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Holiday day off school/work
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Community picnic gatherings
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Family learning tradition
July 2026
4th of July Fireworks Events
Date: Thursday, July 4, evening (8-10PM)
Location: Multiple viewing spots (waterfront, parks)
Official Event Page: City Special Event
Details: Fireworks viewing parties, waterfront picnics, family BBQs.
Why Families Will Love This: Classic holiday tradition, neighborhood block parties, kids get sparklers.
July 2026
Free First Friday
Date: Friday, July 3, evening (5-8PM typical)
Location: Redwood City (10min drive from San Mateo)
Official Event Page: Museum Link
Details: Free museum night, history crafts, ice cream for kids.
Why Families Will Love This: Classic holiday tradition, neighborhood block parties, kids get sparklers.