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.
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.
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.
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.
“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.
Ryan Hardison is a freelance arts and entertainment writer and recent graduate of San Diego State. When he's not staring at his laptop, he's likely eating an adobada burrito or getting sunburnt at the beach.
