May in San Diego means longer days, blooming flowers, and a calendar full of can’t-miss events. This month, locals can sip bottomless mimosas at San Diego Magazine’s Brunch Bash or crack crawfish shells at Gator by the Bay. Music lovers can two-step their way through The Outlaw Festival or vibe with R&B trio Flo, while beachgoers flock to Fiesta Del Sol or the annual Mission Beach Over-the-Line tournament. For fans of the arts, there’s a packed lineup of theater productions and exhibits—including one celebrating the surprisingly adorable armadillo. So grab your tickets, gather your crew, and explore all the best things to do in San Diego this May.
Food & Drink | Concerts & Festivals | Theater & Art Exhibits | More Fun Things to Do
Food & Drink Events in San Diego This May
San Diego Magazine’s 2025 Brunch Bash
May 10
San Diego Magazine presents our annual Brunch Bash, a daytime feast full of unlimited bites, mimosas, and sweet desserts from local restaurants and vendors at Omni La Costa Resort & Spa.
Gator by the Bay
May 8–11
Gator by the Bay, a spectacle of the sounds and eats—like beignets, gumbo, and 10,000 pounds of crawfish—that define Louisiana’s Cajun and Creole culture, brings the bayou to Spanish Landing Park on Harbor Island.
Concerts & Festivals in San Diego This May
Flo at the North Park Observatory
May 11
Fresh off the late 2024 release of their debut album Access All Areas, British R&B girl group Flo stops by the Observatory North Park.
The Outlaw Music Festival at North Island Credit Union Amphitheatre
May 15
The Outlaw Music Festival will celebrate giants of Americana sound—including Billy Strings, Bob Dylan, and Willie Nelson—at the North Island Credit Union Amphitheatre in Chula Vista.
Louis at the Balboa Theatre
May 18
At the Balboa Theatre, an 11-piece jazz ensemble will perform an immersive score to soundtrack Louis, a silent film based on the life of legendary trumpeter Louis Armstrong.
Fiesta Del Sol at Fletcher Cove Park
May 31 – June 1
Hit the beach for Fiesta Del Sol, returning for a sunny weekend at Fletcher Cove Park in Solana Beach. Enjoy free entry, more than 200 vendors, and live music from several local bands.
Theater & Art Exhibits in San Diego This May
Grease at the Moonlight Ampitheatre
April 30 – May 17
Moonlight Stage Productions in Vista kicks off its summer musical season with ’50s nostalgia favorite Grease, a tale of unlikely high school romance that boasts an irresistibly classic soundtrack.
The Prom at the San Diego Music Theatre
May 2 – June 1
The San Diego Musical Theatre production of the musical comedy The Prom arrives in Kearny Mesa right in time for “promposal” season with a funny and moving show of support for LGBTQ students. sdmt.org
Sleeping Beauty at CCA Escondido and Balboa Theatre
May 9 – 11
See the State Ballet Theatre of Ukraine’s dreamy adaptation of Sleeping Beauty, on stage for two nights at the California Center for the Arts, Escondido followed by a Sunday matinee at the Balboa Theatre.
Tuck and Roll: The Art of Armadillos at the Mingei
May 24 – January 11, 2026
The Mingei International Museum draws from its collection to highlight armadillos in all their leather- shelled, spiny-tailed glory with Tuck and Roll: The Art of Armadillos.
A Beautiful Noise at the Civic Theatre
May 27 – June 1
“Sweet Caroline” singer Neil Diamond’s journey from Brooklyn beginnings to musical superstardom unfolds throughout A Beautiful Noise, coming to the Civic Theatre in downtown.
More Fun Things to Do in San Diego This May
The Avant Garde Ball at MCASD
May 3
Embrace the innovative and unconventional in the worlds of art, music, and fashion at The Avant Garde Ball, featuring an open bar, live music, and art installations at the Museum of Contemporary Art San Diego in La Jolla.
Over the Line Beer Fest & Tournament at the Old Mission Beach Athletic Club
May 17
Old Mission Beach Athletic Club celebrates San Diego’s signature sport with local breweries, food trucks, and a community showdown at its Over the Line Beer Fest & Tournament.
