Whether you're feasting on crawfish at the San Diego Crawfish Boil, dancing at the Avant Garde Ball, sampling cheese and local beverages at the San Diego Cheese & Libation Expo, or rocking out with legends at the Outlaw Music Festival, there's no shortage of ways to celebrate spring in America’s Finest City. Below is the ultimate list of top events and activities happening around San Diego this May - all in date order. Mark your calendars and dive into a month of unforgettable experiences!
Grease at Moonlight Stage Productions (April 30–May 17) - The classic '50s musical Grease kicks off Moonlight Stage’s summer season in Vista. Sing along to favorites like "Summer Nights" and "You're the One That I Want" under the stars.
Morrissey at San Diego Civic Theatre (May 1) - The former frontman of The Smiths returns to San Diego for a night of live music, including hits like "There Is a Light That Never Goes Out", "Heaven Knows I'm Miserable Now", and "Suedehead".
The Prom at San Diego Musical Theatre (May 2–June 1) - Celebrate love and acceptance with The Prom, a heartwarming and hilarious musical about supporting LGBTQ+ youth, performed at the San Diego Musical Theatre in Kearny Mesa.
The Prom at San Diego Musical Theatre (May 2–June 1) - Celebrate love and acceptance with The Prom, a heartwarming and hilarious musical about supporting LGBTQ+ youth, performed at the San Diego Musical Theatre in Kearny Mesa.
Julian Woman's Club Wildflower Show (May 2-3) - Head to Julian for a charming display of local wildflowers at Town Hall, celebrating the region’s colorful spring blooms in a quaint, historic setting. This event has been taking place in San Diego County's gold mining town since 1926!
Avant Garde Ball at MCASD La Jolla (May 3) - Enjoy an evening of avant-garde fashion, music, art installations, and an open bar at the Museum of Contemporary Art San Diego's first-ever Avant Garde Ball fundraiser.
San Diego Zoo Food, Wine & Brew Festival (May 3) - Savor Southern California’s best food, wine, and brews while enjoying wild entertainment at this all-inclusive tasting event, supporting wildlife conservation after hours at the world-famous San Diego Zoo.
Killers of Kill Tony (May 3) - Catch the #1 live podcast, Kill Tony, at San Diego Civic Theatre with the Killers of Kill Tony show! Starting at 9:30pm, enjoy comedy from Kam Patterson, Ari Matti, David Lucas, and Martin Phillips. Tickets are $54.30-$64.55.
Walk for Animals San Diego (May 3) - Support the San Diego Humane Society at the Walk for Animals at Liberty Station NTC Park! From 7am to 11am, join 4.3K animal lovers for a walk to raise funds for shelter animals in need.
Gaslamp Cinco de Mayo Festival (May 3) - Celebrate Mexican culture in style at this street fair in the heart of downtown San Diego's Gaslamp Quarter! This vibrant event promises a day of live Latin entertainment across two stages, featuring rhythmic live music, Lucha Libre wrestling tournaments, a dazzling Low Rider Competition and much more.
9th Annual Ocean Beach Pier Surf/Skate Classic (May 3-4) - Surf, skate, and support a good cause at this two-day event in the Ocean Beach Pier Parking Lot! Hosted by A Way of Life and Hodad’s, enjoy surf and skate contests, live music, food trucks, and vendors, benefiting Hodad’s Foundation for youth sports and veterans.
HAMILTON at San Diego Civic Theatre (May 6-18) - Lin-Manuel Miranda’s revolutionary musical HAMILTON returns to San Diego this May for a two-week run at the San Diego Civic Theatre.
Sleeping Beauty by State Ballet Theatre of Ukraine (May 9 & 11) - Witness the enchanting tale of Sleeping Beauty performed by the State Ballet Theatre of Ukraine at California Center for the Arts, Escondido (May 9) and Balboa Theatre (May 11).
Gator by the Bay Festival (May 8–11) - Spanish Landing Park transforms into a Louisiana bayou for Gator by the Bay, a ticked music festival featuring Zydeco, blues, and Cajun music alongside beignets, gumbo, and 10,000 pounds of crawfish.
An Evening with David Sedaris (May 8) - Laugh the night away with David Sedaris at Balboa Theatre in San Diego! Starting at 7:30pm, enjoy an evening of humor and storytelling from the acclaimed comedian and author.
Curebound Concerts for Cures: Elton John (May 9) - The great Sir Elton John is coming out of retirement and returning to San Diego's Petco Park for a night of live music for a worthwhile cause. Expect to hear hits like "Your Song", "Rocket Man", and "Goodbye Yellow Brick Road".
Coronado Art & Wine Festival (May 10) - Sip fine wines and admire works from talented artists at the Coronado Art & Wine Festival, a free-to-attend event featuring live entertainment, culinary delights, and a beautiful island setting.
University Heights Party on Park (May 10) - Join the University Heights Community Association and Appian Way Band for an epic street party on Park Blvd! From 3pm to 7pm, enjoy live music, delicious bites, drinks, shopping from local makers, and tons of fun with 2.1K attendees. Tickets are $20 at zefy.com.
San Diego Magazine's Brunch Bash (May 10) - Brunch lovers unite! Head to Omni La Costa Resort & Spa for an afternoon of bottomless mimosas, sweet and savory bites from San Diego’s top restaurants, and sunshine vibes.
James Taylor at The Shell (May 10 & 11) - The Grammy Award winner and Rock and Roll Hall of Fame American singer-songwriter and guitarist takes over The Rady Shell at Jacobs Park for two nights. Expect to hear hits like "Country Road", Something in the Way She Moves", "Fire and Rain", "You've Got a Friend", and more.
AANHPI Eats Week (May 10-18) - Celebrate Asian American and Native Hawaiian/Pacific Islander Heritage Month with multi-course menus at top San Diego restaurants, honoring AANHPI culinary traditions and stories. Reservations recommended.
Coast of Pacific Beach Restaurant Walk (May 14) - Savor Pacific Beach’s best eats at the Coast of Pacific Beach Restaurant Walk hosted by Discover Pacific Beach! From 4pm to 9pm, enjoy a self-guided food and drink tour along Mission Blvd to Dawes St, with tickets at $35-$50.
Outlaw Music Festival (May 15) - Don't miss Americana legends Billy Strings, Willie Nelson, and Bob Dylan as they bring their Outlaw Music Festival to North Island Credit Union Amphitheatre in San Diego's South Bay city of Chula Vista.
Outlaw Music Festival (May 15) - Don't miss Americana legends Billy Strings, Willie Nelson, and Bob Dylan as they bring their Outlaw Music Festival to North Island Credit Union Amphitheatre in San Diego's South Bay city of Chula Vista.
Chris Isaak at Humphreys Concerts by the Bay (May 15) - Enjoy an evening with Chris Isaak at Humphreys Concerts by the Bay starting at 7:30pm! Packages include dinner for two, premium seats, and a stay at Humphreys Half Moon Inn, with tickets at $126.55
Wonderfront Music & Arts Festival (May 16-18) - Headliners Anderson .Paak, Khruangbin, Peggy Gou, and more bring music, art, and interactive experiences to the downtown bayfront for this San Diego festival’s fourth edition.
San Diego Crawfish Boil (May 17) - The largest crawfish boil in the world and San Diego's best Louisiana-themed event returns to downtown's Waterfront Park. The 36th annual LSU Alumni of San Diego Crawfish Boil is an all-inclusive New Orleans-style party where attendees enjoy nearly 15 tons of boiled crawfish, as well as live music and all-in-all great times. Use promo code SDVILLE to save $5 per ticket or code SDVILLETABLE to save $50 per table for 10.
78th Annual Ocean Beach Kite Festival (May 17) - Enjoy a day of kite flying, games, and family fun at the 78th Ocean Beach Kite Festival hosted by the Ocean Beach Woman’s Club! From 10am to 3pm at Robb Field O.B., this free event features a kite-flying exhibition, craft fair, prizes, and food, open to all ages.
Goldenpalooza Music & Arts Festival (May 17) - Celebrate creativity at the Goldenpalooza Music & Arts Festival at Golden Hill Recreation Center! From 11am to 5pm, enjoy free entry with live music, local vendors, a kids’ zone, and art stations, benefiting Golden Hill UTK-8 school.
Romeo et Juliet by San Diego Ballet (May 17) - Experience the San Diego Ballet’s moving production of Romeo et Juliet at Balboa Theatre! At 2pm, Javier Velasco’s re-staging of Shakespeare’s classic blends lush romance and tragedy, showcasing the timeless star-crossed lovers.
Over the Line Beer Fest & Tournament (May 17) - Celebrate San Diego's original beach sport with the Old Mission Beach Athletic Club’s Over the Line Beer Fest, featuring local breweries, food trucks, and a spirited tournament.
Louis: Silent Film with Jazz Ensemble at Balboa Theatre (May 18) - Experience the magic of the silent film Louis, accompanied by a live 11-piece jazz ensemble performing an original score at the Balboa Theatre in downtown San Diego.
Louis: Silent Film with Jazz Ensemble at Balboa Theatre (May 18) - Experience the magic of the silent film Louis, accompanied by a live 11-piece jazz ensemble performing an original score at the Balboa Theatre in downtown San Diego.
Navy’s 38th Annual Bay Bridge Run/Walk (May 18) - Join Navy Life Naval Base Point Loma for the 38th Bay Bridge Run/Walk at Hilton San Diego Bayfront! Starting at 8am, choose a new 10K or classic 4-mile route across the bridge, presented by Leidos, Port of San Diego, Navy Exchange, and SDGE.
Taste of East Village (May 21 & 22) - San Diego's East Village is set to become a foodie's paradise this May as this self-guided tasting tour returns for two flavorful evenings of food, drink, and community. The culinary crawl invites ticket holders to sample bites and beverages from over 30 of the neighborhood's most popular eateries, bars, and cafés, and promo code SDVILLE saves on tickets.
Santee Street Fair (May 24) - Kick off Memorial Day weekend at the 15th annual Santee Street Fair on Riverview Pkwy! From 10am to 6pm, enjoy 200+ vendor booths, a 21+ beer garden, carnival rides, games, and live music at this free family event hosted by the Santee Chamber.
A Beautiful Noise: Neil Diamond Musical at Civic Theatre (May 27–June 1) - Experience Neil Diamond’s life story and music in A Beautiful Noise, a heartfelt musical journey from Brooklyn to superstardom, coming to the San Diego Civic Theatre for a very limited run.
Fiesta Del Sol at Fletcher Cove Park (May 31–June 1) - Kick off summer at Solana Beach's Fiesta Del Sol, a free, family-friendly festival featuring live music, over 200 local vendors, an arts and crafts area, and plenty of food and drinks.
What a jam-packed month! Shirk the May Gray and get out there to explore America's Finest City. If there are any great events we missed, feel free to send them our way at [email protected] - and we'll be sure to add them to this Ultimate List!
Fiesta Del Sol at Fletcher Cove Park (May 31–June 1) - Kick off summer at Solana Beach's Fiesta Del Sol, a free, family-friendly festival featuring live music, over 200 local vendors, an arts and crafts area, and plenty of food and drinks.
What a jam-packed month! Shirk the May Gray and get out there to explore America's Finest City. If there are any great events we missed, feel free to send them our way at [email protected] - and we'll be sure to add them to this Ultimate List!
Originally published on April 29, 2025.
