Ready to know more about San Diego?


14 Things To Do in San Diego This Weekend: May 16–19

Fly handmade kites in Ocean Beach, experience boundary-pushing performing arts at the International Fringe Festival, and sample Basquait-inspired bites in Logan Heights
San Diego Wine Week featuring a wine-paired dinner event this weekend in San Diego
Courtesy of San Diego County Vintners Association

With the weather finally creeping into the 70s this weekend, here’s a can’t-miss roundup of ways to enjoy the warmth, from a Solana Beach music fest to an all-day tournament for a uniquely San Diego sport. Seeking something more indoorsy? Try a showing of Swan Lake or an enigmatic art exhibition at SDMA, plus 10 more things to do in San Diego this weekend.

Food and Drink | Concerts and Theater | Festivals and Art | More Things to Do 

Jean-Michel Basquiat's sisters Lisane Basquiat and Jeanine Heriveaux at the Basquiat Gala this weekend in San Diego at The Soap Factory
Courtesy of

Food & Drink Events in San Diego This Weekend

San Diego Wine Week: Wine Country in the City

Friday, May 17

The Horton Grand Hotel and Stay Classy Selections will put their stamp on the second annual San Diego Wine Week with a swanky event highlighting the county’s wine heritage this Friday from 5 to 7 p.m. Bringing the rustic vineyard experience to the hotel’s open courtyard, Wine Country in the City will feature selections from 16 local wineries, including Los Pilares, Highland Valley Vineyards, and Ramona Ranch, plus palate-pleasing appetizers to pair with the pours. Tickets are $45 per person.
311 Island Avenue, Gaslamp

Basquiat Gala at The Soap Factory

Saturday, May 18

This year’s iteration of Vanguard Culture’s annual Artist @ The Table fundraiser celebrates the legacy of Jean-Michel Basquiat with appearances from his sisters Lisane Basquiat and Jeanine Heriveaux. Held at The Soap Factory from 6 to 10 p.m. this Saturday, the gala will feature Valle de Guadalupe wines from Baja Wine + Food and Basquiat-inspired appetizers from eight local chefs. Guests can also bid on auction items and enjoy live music from jazz ensemble Cacique and harpist Mariea Antionette. Ticket options include $150 VIP admission, which comes with two drink tickets and access to six chef stations.
2995 Commercial Street, Logan Heights

Fiesta Del Sol music festival event in Solana Beach in North County San Diego this weekend
Courtesy of Belly Up Presents

Concerts & Theater in San Diego This Weekend

San Diego International Fringe Festival 

Through Sunday, May 26

San Diego’s yearly Fringe Festival channels the weird, wacky, and wild of the performing arts world with boundary-pushing productions all over the city. A wide variety of local and international artists will descend upon local venues like the Marie Hitchcock Puppet Theatre and Centro Cultural de la Raza, putting on more than 70 creative, unpredictable, and off-the-wall shows. Admission for each performance ranges from free to $10.

Fiesta Del Sol Festival

Saturday, May 18 & Sunday, May 19

This free, annual, two-day festival from the Solana Beach Chamber of Commerce and The Belly Up features a stacked lineup of musicians playing on the main stage throughout the weekend. Attendees can also enjoy a beer and wine garden, food trucks, a shopping experience at Fletcher Cove Beach Park, and a pancake breakfast served by local firemen. For a more elevated experience, VIP passes ($150 single-day, $250 two-day) come with a meal and drink ticket, a gift bag, a private cash bar, snacks, and reserved cocktail area seating.
111 South Sierra Avenue, Solana Beach

Devil in a Box at the OnStage Playhouse

Opens Friday, May 17

Penned by San Diego playwright Tori Rice and directed by James P. Darvas, Devil in a Box will resonate with anyone who has grappled with addiction or seen its impact in a loved one’s life. There will be 16 performances of the play through June 9 at Chula Vista’s OnStage Playhouse, with three shows this weekend. Tickets are $25 for adults over age 30 (with a $5 discount for students, seniors, and educators) and $15 for those under.
291 Third Avenue, Chula Vista

Swan Lake at the Civic Theatre

Friday, May 17 & Saturday, May 18

The World Ballet Series production of Swan Lake—which is locked in an eternal battle with The Nutcracker for the title of Tchaikovsky’s magnum opus—will arrive at the Civic Theatre this weekend. Soundtracked by a live orchestra, the ballet’s two shows will feature hand-painted sets and dazzling, shimmering costumes. Tickets to Friday and Saturday’s performances of Swan Lake are still available, with prices starting at $75.
1100 Third Avenue, Gaslamp

Community Band Festival at Old Poway Park

Saturday, May 18 & Sunday, May 19

Poway’s annual Community Band Festival showcases groups from all over Southern California playing jazz, bluegrass, and classic concert jams. This two-day festival from the Old Poway Park Action Committee, Pomerado Community Band, and Poway Arts and Crafts Guild will include the sounds of North County Winds, the San Diego Community Jazz Band, and the San Diego British Brass Band. There will also be arts, craft, and music merchandise vendors and food service throughout the weekend (10 a.m. to 7 p.m. Saturday and Sunday) at Old Poway Park.
14134 Midland Road, Poway

Artist and Painter Jasper Johns' piece titled "Perilous Night" featured in the San Diego Museum of Arts this weekend
Courtesy of Jasper Johns

Festivals & Art Exhibits in San Diego This Weekend

Street Level 2.1 at the Oceanside Museum of Art

Friday May 17

Coastal Exposures: 10 Years of Osider Photography will be the first exhibition to get the block party treatment at volume two of the Oceanside Museum of Art’s Street Level series. This Friday from 6 to 8:30 p.m., OMA will get the summertime vibes started with spins from DJ Chaps One, tunes from Devvlov and The Dappersons, bites from 7 Siblings, and a lowrider showcase from a pair of O’side car clubs: Members Only and Por Siempre. Street Level 2.1 is free for all OMA members and $15 for non-members; through May 17, you can purchase a $60 season pass that comes with admission to all five 2024 Street Level events.
704 Pier View Way, Oceanside

Ocean Beach Kite Festival

Saturday May 18

The Ocean Beach Kiwanis Club’s annual kite-flying get-together encourages San Diegans to take flight with homemade kites. From 10 a.m. to 3 p.m. at Robb Athletic Field, the 77th Ocean Beach Kite Festival will offer attendees the chance to make, decorate, and fly their very own kite and enjoy food, games, live music, and an exhibition from pro kitefliers. This classic SD event is free for all.
2525 Bacon Street, Ocean Beach

America on Main Street in El Cajon

Saturday May 18

Every year, downtown El Cajon holds a neighborhood street fair celebration highlighting the spirit of the USA as a melting pot for diverse cultures and communities. America on Main Street features a wide variety of arts, crafts, and international food booths, plus carnival rides, bounce houses, a petting zoo, and live entertainment stages. As a special part of this year’s street fair, attendees can sample all-you-can-eat appetizers, sweets, and drinks from more than 10 local restaurants and vendors in the Foodie Fest area. General admission is $20 for adults and $10 for kids ages 6 to 12; entry is free for children ages five and under.
East Main Street and Rea Avenue, between Magnolia and Claydelle Avenues, El Cajon

Asian Cultural Festival of San Diego 

Saturday May 18

The 11th annual Asian Cultural Festival of San Diego takes place this Saturday from 12 to 8 p.m. The free fest features all-day folk and contemporary entertainment, sizzling street food, and refreshing fruit flavors, highlighting more than a dozen Asian countries’ cultures and traditions. Those who stop by Mira Mesa Community Park can also expect a beer garden, martial arts demos, a video game tent, an escape room, a ramen-eating contest, and more. 
8575 New Salem Street, Mira Mesa 

Jasper Johns: Drawings and Prints at SDMA

Opens Satuday May 18

Opens May 18

Through October 27, the San Diego Museum of Art will display 14 works from artist and printmaker Jasper Johns’ six-decade-plus career. Don’t miss Green Angel, a 1991 etching with a distinctive and intriguing motif possibly inspired by a Rodin sculpture.
1450 El Prado, Balboa Park

Dance group performing at Shock'N The Park hip hop dance event at Liberty Station, San Diego this weekend
Courtesy of Culture Shock San Diego

 More Fun Things to Do in San Diego This Weekend

Over the Line Craft Beerfest & OTL Tournament in Mission Bay

Saturday May 18

One of San Diego’s most storied sporting customs returns to the sands of Mission Bay this Saturday. Dozens of local players will team up to play over-the-line all day (7 a.m. to 6 p.m.) at Old Mission Beach Athletic Club’s eighth annual OTL Craft Beerfest & Tournament. From 11 a.m. to 3 p.m., attendees can also enjoy bites and suds from San Diego’s best breweries and food trucks at Mariner’s Point. General admission tickets to this 21-plus event are $40 and can be purchased here; team entry for the OTL tournament is sold out.
1215 Mariners Way, Mission Bay

Shock’N The Park at Liberty Station

Sunday May 19

Culture Shock San Diego’s yearly ode to b-boys and hip-hop culture returns this Sunday from 12 to 4 p.m. to Liberty Station’s Legacy Plaza. San Diegans can stop by and root for their favorite local troupes as they battle it out on the dance floor. Then, watch a two-hour dance showcase that includes a special performance from acrobat, choreographer, and Liberty Station Arts District artist-in-residence Micah Parra.
2641 Truxtun Road, Point Loma

By Ryan Hardison

Ryan Hardison is a freelance arts and entertainment writer and recent graduate of San Diego State. When he's not staring at his laptop, he's likely eating an adobada burrito or getting sunburnt at the beach.

Share this post

Contact Us

1230 Columbia Street, Suite 800,

San Diego, CA