Karen DeGasperis REALTOR

San Diego Calendar of Events – May 2025

San Diego May 2025 Events Calendar

When: Now - May 11, 2025

The Flower Fields at Carlsbad Ranch in California bloom with nearly 50 acres of vibrant Giant Tecolote Ranunculus flowers each spring, offering a stunning display for six to eight weeks.

When: May 2-3, 2025

If you enjoyed our Virtual Wildflower Show, don’t miss the 2025 Wildflower Show! Where you can see, smell, and experience the stunning Jewels of the Backcountry in person.

When: May 2 – May 18

Feel the rhythm and flavor at Viva La Música and SoCal Taco Fest at SeaWorld San Diego — a lively fusion of Latin music, tacos, Lucha Libre, and nonstop fiesta vibes, all included with park admission!

When: May 3, 2025

Time: 11 AM – 7 PM

Gaslamp Downtown & Old Town San Diego
Make it a Cinco de Mayo weekend to remember in San Diego, with epic celebrations in the
Gaslamp and lively fiestas at Old Town’s Fiesta de Reyes!

When: May 3, 2025

Rancho Bernardo Inn presents a special James Beard Winners Dinner — a six-course culinary experience featuring award-winning chefs, Food Network stars, and a celebrity mixologist for one unforgettable evening.

When: May 3, 2025

Experience a wild night at the San Diego Zoo with Southern California’s top food, wine, and beer, plus live entertainment and dancing—all at this one-of-a-kind tasting event

When: May 4, 2025

Cruise into vintage vibes at Coronado’s classic car show with 400+ stunning rides, live music, prizes, and free seaside fun just steps from the beach!

When: May 4, 2025

Kick off your race season with the Spring Sprint Triathlon, Duathlon & Aquabike in San Diego! Featuring a calm bay swim and flat bike and run courses, it’s the perfect way to jumpstart your year and hit the ground running or swimming and biking!

When: May 8-11, 2025

Get your Southern vibes on at Gator By The Bay, San Diego’s ultimate four-day Louisiana-style festival packed with live music, dancing, and 10,000 pounds of crawfish by the bay!

When: May 10, 2025

Time: (2pm – 10pm)

Get ready for the return of Tacos & Beer Fest — a vibrant celebration packed with food, drinks, live entertainment, and a special tribute to Mexican Mother’s Day!

When: May 11, 2025

Celebrate Mom with the ultimate Mother’s Day getaway in sunny San Diego from spa days to seaside brunches, special deals, and endless ways to make her feel unforgettable!

When: May 16-18, 2025

Enjoy a 3-day festival of music, food, and art along the Embarcadero, featuring yacht parties, water sports, art installations, after-parties, a craft beer village, and local flavors.

When: May 17, 2025

Kick off summer at the 7th annual Over the Line tournament at Mariners Point, featuring San Diego’s top craft breweries, food trucks, and plenty of fun—so grab your bat and join the action!

When: May 17, 2025

Soar into fun at the Annual Ocean Beach Kite Festival — the oldest children’s kite festival in the country! Enjoy free kite making, decorating, and flying, plus jaw-dropping demos from top kite pros. With live music, games, delicious food, and a lively street fair, it’s a family day out you won’t want to miss. No wonder Westways Magazine named it one of the “five worth the drive”!

Experience breathtaking coastal views at the La Jolla Half Marathon & 5K! Starting at the Del Mar Fairgrounds, this iconic race winds along the San Diego coast, tackles the climb through Torrey Pines, and finishes at stunning La Jolla Cove. Want a shorter challenge? The 5K offers a scenic, mostly downhill course you’ll love!

When: May 18, 2025

Take in breathtaking views at the Coronado Bay Bridge Run/Walk! This unique 4-mile course leads you from downtown San Diego over the iconic bridge to beautiful Tidelands Park a one-of-a-kind experience you won’t want to miss!

When: May 24, 2025

Time: 10 AM – 6 PM

Celebrate 15 years of fun at the Santee Street Fair & Craft Beer Festival, featuring local brews, 300+ vendors, live entertainment, a kids zone, and excitement for the whole family!

When: May 24, 2025

The Asian Cultural Festival of San Diego is the city’s largest celebration of Asian Pacific American Heritage Month, featuring traditional performances from over a dozen countries and cultures.

When: May 25, 2025

Time: 8 AM – 6 PM

Celebrate 14 years of sweet fun at the Vista Strawberry Festival with tasty treats, live entertainment, a 5K run, and more in Downtown Vista!

When: May 25 - August 31, 2025

Celebrate 55 years of music with the 2025 Coronado Promenade Concerts, featuring 16 summer shows, fresh new bands, fan favorites, and a special Military Appreciation Day with Nashville’s SixWire and a surprise guest!

When: May 26, 2025

This Memorial Day, honor our fallen heroes in San Diego with heartfelt tributes and ceremonies and welcome the unofficial start of summer with moments of reflection and celebration.

When: May 26, 2025

Honor our heroes at the Fort Rosecrans Memorial Day Celebration, one of San Diego’s largest tributes to the brave men and women who made the ultimate sacrifice.

When: May 30-31, 2025

The Kuumba Festival returns safely to Encanto’s 4th District—San Diego’s longest-running celebration of Black youth, family, community, health, art, culture, and heritage.