As we step into May, Simi Valley is buzzing with a variety of events catering to all interests. Here’s a roundup of some notable happenings you won’t want to miss:
Simi Valley Street Fair
Date: Saturday, May 2, 2026
Time: 9:00 AM – 4:00 PM
Location: Simi Town Center Way
The annual Simi Valley Street Fair returns, featuring artisan craft vendors, delicious food, a free Kids’ FunZone, live music, and a beer and wine garden. It’s a perfect outing for families and friends to enjoy the community spirit. Learn more.
Sunday Night Comedy
Date: Sunday, May 3, 2026
Location: Simi Valley Cultural Arts Center
Enjoy an evening of laughter with talented comedians at the Cultural Arts Center. A great way to wrap up your weekend with some humor and entertainment. More details.
Happy Face Music Festival ’26
Date: Saturday, May 23, 2026
Time: 10:30 AM – 7:00 PM
Location: Rancho Santa Susana Community Park
Celebrate Memorial Day weekend with live music and entertainment at the Happy Face Music Festival. Bring your blankets and lawn chairs to enjoy performances from bands like Bee Gees Fever and The fABBA Show. Food trucks and beverages will be available. Get tickets.
Fiddler on the Roof
Dates: May 30 – June 28, 2026
Location: Simi Valley Cultural Arts Center
Experience the classic musical “Fiddler on the Roof” performed by local talent. This production promises to be a highlight of the season. Purchase tickets.
These events showcase the vibrant community spirit of Simi Valley. Mark your calendars and enjoy what our city has to offer this May!