Free Outdoor Summer Entertainment In San Mateo County

REDWOOD CITY, CA — The City of Redwood has a long list of free and fun outdoor entertainment movies, music and more that will kick off May 30 with Music on The Square every Friday, featuring local musicians and bands.

Here is the full list of events:

Weekly Event Series 2025

Wednesdays: Music in the Park
June 18 - August 20, 6 p.m. - 8 p.m.
at Stafford Park*
https://www.redwoodcity.org/mu...

Thursdays: Movies on the Square
June 5 - August 28
Now showing double features!
Kids Movies at 6 p.m. / Independent Films at 8 p.m., Main Feature at 8:30 p.m.
Juneteenth Celebration on 6/11 featuring Black Independent Filmmakers with Bravemaker Films at 8 p.m.
https://www.redwoodcity.org/mo...

Fridays: Music on the Square
May 30 - August 29, 6 p.m. - 8 p.m.
https://www.redwoodcity.org/musiconthesquare

Other Event Series & Unique Events 2025

Saturdays: Pub in the Park
11 a.m. - 4 p.m.
May 31, July 12, August 2, September 6
at Red Morton Park*
https://www.redwoodcity.org/pu...

NOW ON Saturdays: Kids Rock!
10 a.m. - 12 p.m.
June 28, July 19, August 9
https://www.redwoodcity.org/ki...

NOW ON Saturdays: Sounds of the Shores
5 p.m. - 7 p.m.
June 28, July 19, August 9
at Marlin Park*
https://www.redwoodcity.org/re...

Art on the Square
ART on the Square: Friday 6/20, 5:00-8:30 p.m.
JEWELRY on the Square: Friday 7/11, 5:00-8:30 p.m.
ART on the Square: Friday 7/25, 5:00-8:30 p.m.
ART on the Square: Friday 8/22, 5:00- 8:30 p.m.
https://www.redwoodcity.org/ar...

Shakespeare in the Park - The Two Gentleman of Verona
Saturdays & Sundays, August 9 - 24, 6 p.m.
at Red Morton Park*
https://www.redwoodcity.org/sh...

Classical Music on the Square - Redwood Symphony Performance
Saturday June 21, 7 p.m.
https://www.redwoodcity.org/classical
Oktoberfest Redwood City - Extended Dates!
Friday September 19 - Sunday September 21
Tuesday September 23 - Sunday September 28
Matinée and Evening seatings
https://www.redwoodcity.org/ok...

Zoppe F a.m.ily Circus
Starting Friday, November 1, matinée and evening show times
Ticketed Event
Redwood City Library Parking Lot**
https://www.redwoodcity.org/zoppe

Series Schedules

Wednesdays: Music in the Park
In Stafford Park, June 18 through August 20 6 p.m.-8 p.m.

June 18 San Benito County Line
June 25 Tempest
July 2 Top Shelf
July 9 Jimbo Scott & Yesterday's Biscuits
July 16 Andre Thierry
July 23 Jokers and Thieves
July 30 Jessica Johnson Band
August 6 Pacific Vibration
August 13 Michelle L a.m.bert
August 20 Sinister Dexter

Thursdays: Movies on the Square

June 5 through August 28. Now showing double features!

First listed is Main Feature at 8:30 p.m. Second listed is Kid's Feature at 6 p.m.

All other dates, Bravemaker Independent Films at 8 p.m.

June 5 Twisters
June 12 Mean Girls (The Musical)
Despicable Me 4
June 19 Bob Marley: One Love
June 26 Dune Part 2
July 3 NO MOVIE JULY 4th
July 10 Juneteenth Bravemaker Films
July 17 Jaws
Inside Out 2
July 24 Wicked
July 31 Sonic the Hedgehog 3
Moana 2
August 7 Beetlejuice Beetlejuice
August 14 Godzilla x Kong: The New Empire
The Wild Robot
August 21 Clueless
August 28 Argylle
Kung Fu Panda 4

Saturday: Classical Concert on the Square

June 21, 7 p.m. Redwood Symphony Performance

Saturdays: Pub in the Park, 11 a.m.-4 p.m. in Red Morton Park

May 31 Wildcat Mountain R a.m.blers
July 12 Stragglyrs
August 2 Purple Mountain Majesty
September 6 Savannah Blu

Other City Events
Friday Night Fundraiser – May 31, 5:30 p.m.-8 p.m.

Downtown Redwood City Car Show – June 7, 10 a.m.-3 p.m.
Independence Day – July 4, Parade @ 10 a.m.; Firework Festivities at Port of Redwood City, 6 p.m.-10 p.m.
Chalk Festival – July 3 & 4th All Day Downtown
Picnic en Blanc – August 16
Lebanese Festival – August 23, 10 a.m.-3 p.m.
Fiesta Patrias – September 14, 3 p.m.-8 p.m.
Port Fest – October 5, 11 a.m.-3 p.m.

The first group of events runs every week during the scheduled time.
Events are free and all happen downtown on Courthouse Square in Redwood City at 2200 Broadway, unless otherwise noted with*.