May 2025 Bay Area Arts & Culture Highlights
May brings a wealth of performing arts, music, and culture to the Bay Area—an ideal time for theater lovers, festival-goers, and anyone eager to be inspired by live performance.
From a legendary tenor in Napa Valley to Shakespearean comedy in downtown San Francisco, there’s something for every kind of arts enthusiast.
Below is our curated roundup of standout events to consider this month across San Francisco, Berkeley, Mountain View, and beyond.
Bay Area Arts Highlights – May 2025
Andrea Bocelli at Charles Krug Winery
June 21–22, 2025 – St. Helena, Napa Valley
World-renowned tenor Andrea Bocelli returns to Napa for two magical evenings at the historic Charles Krug Winery. This intimate outdoor concert is part of “A Weekend in Napa” and promises a transcendent blend of classical music and wine country ambiance. More info.
Berkeley Repertory Theatre – 2025–26 Season Launch
Berkeley Rep kicks off its season with bold new works including three world premieres. Highlights include The Reservoir, a lyrical portrait of recovery, and Mother of Exiles, a time-jumping epic spanning from 1898 to a climate-ravaged 2063. Season announcement.
The Curious Incident of the Dog in the Night-Time – SF Playhouse
May 1 – June 21, 2025 – San Francisco
This Tony-winning play immerses audiences into the extraordinary mind of a teenage protagonist navigating a mysterious incident—and the wider world—on his own terms. Tickets and details.
Two Trains Running – ACT
April 15 – May 4, 2025 – San Francisco
August Wilson’s powerful drama explores the African American experience in 1960s Pittsburgh through the lens of a local diner. Timely, poetic, and steeped in community. More info.
Yerba Buena Gardens Festival – 25th Anniversary Season
Opens May 10, 2025 – San Francisco
This beloved free outdoor festival returns with a high-energy launch featuring Grammy-winners La Santa Cecilia and Bay Area sensation La Doña. The summer season promises dozens of multicultural music, dance, and performance events in the heart of downtown. Festival lineup.
The Comedy of Errors – ACT
April 22 – May 3, 2025 – San Francisco
Shakespeare’s classic farce of mistaken identity, brought to the stage with wit and energy by ACT. A smart, satisfying theatrical romp. Show info.
Cinco de Mayo Celebrations Across the Bay
May 3 – May 10, 2025
Parades, mariachi concerts, and lowrider shows will light up the streets across the Bay Area in celebration of Mexican culture and heritage. Notable events in San Francisco, Hayward, Richmond, and San Jose. Event guide.
Here There Are Blueberries – Berkeley Rep
April 5 – May 11, 2025 – Berkeley
A haunting docudrama by Moisés Kaufman and Amanda Gronich that begins with a mysterious photo album from Auschwitz—and ends in a searing examination of historical complicity. Get tickets.
Looking ahead, summer previews and season announcements are beginning to roll in across the Bay Area. Stay tuned to Stark Insider for updates on outdoor festivals, wine country performances, and fall theater programming.
For the full spectrum of West Coast culture—from espresso to Shakespeare—you know where to find us.
