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San Diego's Best Events in May

How to be busy and important this month in San Diego


May 2:

Mariachis, margaritas, and Mexican food abound at the “hot, hot, hot” Fiesta Old Town Cinco de Mayo weekend celebration.

Wine, Women, and ShoesWine, Women, and Shoes

May 3:

Wine tasting + shoe shopping = the perfect Saturday afternoon in support of Voices for Children at the Wine, Women and Shoes fundraiser in Rancho Santa Fe.

May 4:

More than 100,000 shoppers descend on downtown Carlsbad to stroll the Carlsbad Village Faire.

Meanwhile, more than 400 classic autos cruise into Coronado at Motor Cars on Main Street.

May 5:

If there’s a punk rock mariachi band performing, it must be a Cinco de Mayo Party at the Belly Up.

San Diego Surf Film FestivalSan Diego Surf Film Festival

May 7:

Catch a wave, catch a flick, or catch them both at the four-day San Diego Surf Film Festival at Bird’s Surf Shed.

May 8:

Live it up like a Louisiana local and get your groove on at the four-day Gator by the Bay zydeco, blues, and crawfish festival.

May 10:

Fly high with hippies and families alike at the OB Kite Festival.

Celebrate Asian Pacific American Heritage Month with food and family-friendly fun at the Asian Cultural Festival.

Near the Oceanside Pier, Rubio's Coastfest includes a beach cleanup, food, music, and beer garden.

May 11:

Whether it’s a Champagne brunch cruise on the bay or an upscale dinner downtown, whatever you do, don’t forget Mom on Mother’s Day.

May 14:

Three words say it all: Eat. Drink. Read. with dozens of San Diego chefs dishing it out in support of literacy.

May 16:

Giddy up and escape the city for some countrified fun at the Ramona Rodeo.

May 17:

It’s booth after booth of artsy bliss—including a Craft Beer Block—at the North Park Festival of Arts

Calling all country fans! Megastar Tim McGraw performs live at Sleep Train Amphitheatre.


May 18:

Manicotti, cannoli, Chianti, oh my! Feast on the flavors of (Little) Italy at the Sicilian Festival.

Fight your fear of heights and conquer the Coronado Bay Bridge in the Navy’s Bay Bridge Run/Walk.

May 19:

Scripps Health celebrates survivorship at its annual Concert for Cancer featuring blues artist Keb’ Mo’ at Humphreys Concerts by the Bay.

May 23:

Witness the strength of workout wonders at the Reebok CrossFit Games at the Del Mar Arena.

Omni La Costa Resort and Spa hosts a hot lineup of cool jazz at the three-day San Diego Jazz Festival

American Freedom FestivalAmerican Freedom Festival

May 24:

Kick off your Memorial Day Weekend by waving your red, white, and blue in concert with some “world classic rockers” at the American Freedom Festival on board the USS Midway.

May 25:

Take a culinary tour around the world via Balboa Park at the Ethnic Food Fair at the House of Pacific Relations International Cottages.

May 27:

Get ready to laugh yourself religiously silly at the Tony-award winning Best Musical, The Book of Mormon, from the creators of South Park.

Bacon CupcakesBacon Cupcakes | Photo by Jeremy Ball - Bottle Branding

May 31:

Please your palate all day long at the Bacon and Barrels Festival. Visit 140 booths in the Embarcadero Marina Park South for bourbon, beer, and dishes featuring bacon. There will be an all-bacon dinner for VIPs (Very Important Pigs).

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