Table of Contents
⚾ Sports & Outdoor Events
La Jolla Half Marathon
May 17
Ready to run 13.1 miles with views better than your last vacation? The La Jolla Half Marathon serves ocean breezes, hilltop climbs, and bragging rights on a silver platter. It’s the only time sprinting past sea lions is encouraged!
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Ocean Beach Kite Festival
May 17
Let your inner child (and actual kids) soar with joy at the Ocean Beach Kite Festival! Whether you’re flying high or just here for the breezy vibes and neon skies, it’s a perfect excuse to act like a kid—no strings attached. Bring sunscreen, a kite, and your best wind-resistant hat.
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San Diego Padres vs. Seattle Mariners
May 16–18
Sunshine, hot dogs, and high-stakes West Coast baseball—what more could you want? The Padres take on the Mariners at Petco Park, and the only thing swinging harder than the bats will be the fans doing the wave. Batter up, San Diego—this is your weekend to catch some serious SoCal sports energy!
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Over the Line Beer Fest & Tournament
May 17
Sun’s out, buns out—it’s Over the Line time! This iconic San Diego mash-up of sand, beer, and wildly creative team names is the ultimate way to kick off summer. Swing by for good vibes, cold brews, and balls flying in every direction (some more intentional than others).
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🎶 Music & Festivals
Outlaw Music Festival
May 15
Break out your bandana and dust off that old cowboy hat—Outlaw Music Festival is galloping into town! Expect legendary tunes, legendary vibes, and possibly Willie Nelson sightings (no promises, but manifest it). It’s like a country-fried block party with better guitar solos and less small talk.
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Wonderfront Music & Arts Festival
May 16–18
Beach views, boat rides, and a music lineup hotter than a Mission Beach bonfire. Wonderfront is back, ready to turn the waterfront into one giant three-day jam session. Don’t forget to stretch—your dance moves will be needed.
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The Used – 25th Anniversary Tour
May 15–16
Break out the eyeliner and scream your heart out—The Used is back to make your teenage angst feel seen (again). With 25 years of emo anthems under their belt, this is the nostalgia-fueled pit you didn’t know you needed. If you’re not hoarse by the end of the night, you’re doing it wrong.
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Ryan Adams: Heartbreaker ‘25 World Tour
May 16
Ryan Adams is back to break hearts and hit the high notes that got you through your early 2000s angst. Catch him live as he dusts off his iconic ‘Heartbreaker’ album—and maybe your feelings. Bring tissues… and maybe a locket of your ex’s hair for old time’s sake.
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Goldenpalooza
May 17
Is it a music fest? Is it a dog party? It’s both—and it’s pawsitively golden. Join a sea of goldens and their humans grooving to local tunes, because nothing says San Diego spring like live music and wagging tails.
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Chris Isaak Concert
May 15
Put on your best pompadour and prepare to swoon — Chris Isaak is crooning his way into San Diego! Whether you’re heartbroken or just here for the vibes, his velvet voice might just fix your love life. Bonus: it’s at Humphreys, so the bay breeze is included free of charge.
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🍷 Food & Drink Events
Cheese & Libation Expo
May 16–18
Cheese and booze? Yes, please! Swirl your wine and sniff your brie at San Diego’s classiest pairing party. Perfect for curd nerds and cocktail connoisseurs alike.
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San Diego Crawfish Boil
May 17
Pinch, peel, and party like you’re in the bayou! This crawfish boil is bringing Louisiana flavor to San Diego, and trust us—you don’t want to miss the chance to get messy in the most delicious way possible.
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🎭 Theater & Performing Arts
Hamilton
May 6–18
If you haven’t seen Hamilton yet, what in the name of King George are you waiting for? Lin-Manuel Miranda’s unstoppable musical revolution finally hits San Diego, and trust us—this one’s worth forfeiting your dueling pistols for. History’s never been this catchy or this cool.
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San Diego International Fringe Festival
May 15–25
From mind-bending mime to musicals about sentient toasters, the San Diego International Fringe Festival is where weird meets wonderful. It’s 10 days of daring performances that’ll leave you laughing, gasping, and possibly Googling what you just saw. Come for the fringe, stay for the glorious unpredictability!
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Romeo et Juliet (Ballet)
May 17
Love. Pirouettes. Tragedy… but make it en pointe! Catch San Diego Ballet’s dramatic take on Shakespeare’s most iconic couple—it’s like high school English class, but with better costumes and fewer pop quizzes.
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Jaja’s African Hair Braiding
May 17–June 15
From braids to bold dreams, this high-energy salon set is buzzing with life, laughter, and legendary side-eye. If you’ve ever spilled tea while getting your edges laid, this one’s for you. Come for the drama, stay for the deep conditioning.
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LOUIS: A Silent Film
May 18
Move over Charlie Chaplin—this silent film comes with a live jazz score by none other than Wynton Marsalis. ‘Louis’ is like time traveling back to 1920s New Orleans, but with better seats and fewer flappers. Catch it at the San Diego Theatres and pretend you’re a fancy film aficionado (pinky out optional).
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