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San Diego's Best Events in May

Exciting things come to the city this month!


April 28:

A library at the mall? Give a warm literary welcome to Otay Ranch Town Center’s newest addition at the annual Bon Appetit: An Affair to Celebrate Food, Wine, and Our Libraries. $35.

Bicyclers celebrate their love of two wheels and the beautiful EastLake surroundings at the annual Cycle EastLake benefit for public schools.

April 29:

Grab a jug of water—it’s about to get spicy at the Rootin’ Tootin’ Chili Cook-off and Fair at the Chula Vista Golf Course in Bonita.

May 1:

Actor/producer Rita Wilson (aka Mrs. Tom Hanks) is an aspiring singer/songwriter?! See her on stage at Anthology, previewing her debut album. $10 and up.

Celebrate May Day with an adrenaline-pumping adventure courtesy of Jamul-based SkyDive San Diego, which flies you over Otay Lakes before a 13,000-foot free fall.

May 2:

Jsix chef Christian Graves cooks with consciousness, presenting four weeks of gluten-free prix fixe menus during Celiac Awareness Month. $30.

May 3:

All month, St. Germain’s Bistro and Café in Encinitas celebrates the female chef with its second installation of the Lady Chef Series, featuring food by Food Farm Truck’s chef, Kari Rich.

May 4:

Enjoy a three-day extravaganza of Mexican food, music, and culture at the free Fiesta Old Town Cinco de Mayo.

May 5:

La Jolla Cove serves up wine, beer, and food galore at Island Divine, Junior League of San Diego’s premier fundraiser. $70 and up.

May 6:

La Jolla Symphony and Chorus celebrates the change of season with two days of Spring Symphonies at UCSD. $15 and up.

Downtown Chula Vista’s Third Avenue is home to the annual Festival Cinco de Mayo, featuring such hit events as the Quinceañera Extravaganza, Mariachi Band Battle, and the spicy dish contest. Free.

May 8:

Model Christie Brinkley stars as cold-hearted killer Roxie Hart in the Broadway/San Diego production of Chicago.

May 10:

The Museum of Photographic Arts screens 1971 classic Harold and Maude at the Coming of Age Film Festival. $8.

Every Thursday night the music scene sizzles in Barrio Logan at the free Latin Jazz Jam at Voz Alta Project Gallery, a grassroots space to promote cross-cultural artwork.

May 11:

More than 50 local chefs and host Sam the Cooking Guy serve up a gourmet feast at Mama’s Day, in support of Mama’s Kitchen. $125.

The bayou comes to SD at the three-day Gator by the Bay festival. $25 and up.

Flock to Cricket Wireless Amphitheatre for the Channel 93.3 Summer Kickoff Concert featuring a lineup including Wiz Khalifa, Flo-Rida, The Wanted, and Maroon Five. $40 and up.

May 12:

City Ballet presents Shakespeare’s tragic romance Romeo and Juliet. $29 and up.

Celebrate Asian Pacific Islander Heritage Month at the Asian Cultural Festival at NTC Promenade.

Nibble on sweet treats at the San Diego Botanical Garden’s Chocolate Festival. $12.

Visit the source of your favorite restaurants’ farm-fresh produce. Head for the Second Saturday Harvesting Tour at Suzie’s Farm, a 70-acre organic farm in the Tijuana River Valley. $10.

May 13:

Treat Mom to a whale of a good meal at SeaWorld’s Mother’s Day Brunch with Shamu. $29 and up.

Get an inside peek at the good life on the Coronado Historic Home Tour. $35 and up.

Take a trippy trip back in time to the psychedelic ’70s at the return of Roger Waters – The Wall Live. $59 and up.

May 14:

Burlesque beauty Dita Von Teese brings her “Strip Strip Hooray” variety show to San Diego’s House of Blues for two nights of sultry entertainment. $46 and up.

May 15:

ArtPower! UC San Diego looks back at the early works of big-time directors in the fifth annual Press Rewind event, kicking off the Up & Coming Student Film Festival. Free.

May 16:

The name says it all at Eat Drink Read, a culinary benefit for the San Diego Council on Literacy, held at NTC Promenade. $60.

May 17:

San Diego Magazine honors the city’s smartypants during the Top Tech Exec Awards at The Paddock at the Del Mar Fairgrounds. $35.

Feast on multicultural fare at the 21st annual Taste of National City at Heritage Square. $20.

May 18:

When your coworkers ask why you’re still wearing your helmet in your cubicle, tell them, “It’s how I roll” on National Bike to Work Day. Learn about free pit stops with refreshments and t-shirts.

May 19:

Prepare for the summer BBQ season and celebrate National BBQ Month by learning to throw the perfect luau at Iowa Meat Farms and Siesel’s Meats Sweet Onion and BBQ Festival.

Run like an Olympian—or at least run/walk past one in training—at the fourth annual 5K Chula Vista Community Fun Run at the Olympic Training Center. $25 and up.

Celebrate Filipino-American culture and the 114th anniversary of Philippine independence at the Philippine Faire and Festival of Festivals Parade at the Robert Egger Sr. South Bay Recreation Center. Free.

May 20:

Mangia, mangia! The feasts and festivities never stop in Little Italy. This month’s free Festa Siciliana is no exception.

In North Park, music lovers, artisans, and craft beer lovers are out in full force at the annual Festival of the Arts.

It may not be for the faint of heart or those afraid of heights, but The Navy’s 26th Bay Bridge Run/Walk is certainly a unique opportunity to cross the Coronado Bay Bridge on foot—while raising money for the Navy’s Morale, Welfare, and Recreation programs.

May 22:

You know him as Dr. House, but on stage at the Belly Up, he’s Hugh Laurie. Watch him bring down the “house” (ouch) by singing the blues. $50 and up.

May 23:

See the Old Globe's Scottsboro Boys, with music and lyrics by Kander and Ebb - and choreography by Susan Stroman!

May 25:

The quintessential California band, the Beach Boys, reunite for their 50th anniversary, bringing “Good Vibrations” to the Cricket Wireless Amphitheatre. $45.50 and up.

May 26:

At the Tijuana Estuary in Imperial Beach, a free guided Nature Walk introduces guests to all the wildlife that abounds in the South Bay.

May 30:

Fifteen local chefs compete for the titles of “Best Poke” and “Surprise Poke” at the I Love Poke Festival at Bali Hai Restaurant. Live music and beer from Kona Brewing Company cap off this festive Hawaiian contest.

June 2:

The Chula Vista Nature Center celebrates its critters with fine cuisine and world-class wine at the Where the Wild Things Are Food and Wine Classic.

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