Ready to know more about San Diego?

Subscribe

16 Things to Do in San Diego This Weekend: May 14–18

Observe the evolution of Filipino food at “Taste San Diego,” venture through the secret gardens of La Jolla, and enjoy live music all weekend long at Wonderfront
Fun things to do in San Diego this weekend May 14-18, 2025 featuring the Wonderfront Music Festival at the Embarcadero
Courtesy of Hitmarkgroup

This weekend in San Diego is filled to the brim with good eats and fun festivals. Enjoy unlimited dairy and drinks at the Cheese & Libation Expo, chow down at an LSU alumni–led seafood boil at Waterfront Park, and explore the interactive Taste San Diego exhibition at the San Diego History Center. Music superstars will perform all over the city, with Bob Dylan and Willie Nelson headlining the Outlaw Music Festival and the Wonderfront Festival offering its best lineup yet. Plus, fans of the performing arts can enjoy diverse shows at the San Diego International Fringe Festival, and San Diegans can fundraise for local education at the first-ever Goldenpalooza.

Food & Drink | Concerts & Festivals | Theater & Art Exhibits | More Fun Things to Do

Fun things to do in San Diego this weekend May 14-18, 2025 featuring a flyer for the Cheese & Libation Expo 2025 at BRICK in Liberty Station
Courtesy of Cheese & Libation Expo

Food & Drink Events in San Diego This Weekend

Cheese & Libation Expo 2025 at BRICK

May 16–18

Calling all cheeseheads: The Cheese & Libation Expo returns to BRICK Liberty Station this weekend with an unbrie-lievable spread. The expo begins Friday with the Maker’s Night trade show and will be followed by three tasting sessions Saturday and Sunday. Attendees can enjoy unlimited cheese, bottomless drinks, delicious pairings, bites from Dinner Bell SD, and boutique shopping. Ticket options include individual general admission ($77 per session) and weekend passes ($162). If you purchase your pass through a special donation link, $25 of the ticket price will go toward Anvil of Hope, Berry Good Food Foundation, or Zero Foodprint

2863 Historic Decatur Road, Point Loma

Over the Line Beer Fest & Tournament at the Old Mission Beach Athletic Club

May 17

Sports and suds will team up this Saturday at the annual Over the Line Beer Fest & Tournament, a warm-up for Old Mission Beach Athletic Club’s world championships in July. From 7 a.m. to 6 p.m. at Mariner’s Point Park, attendees can cheer on several teams as they compete head-to-head in games of over-the-line and enjoy food trucks and unlimited beer tastings from 20 San Diego County breweries from 11 a.m. to 3 p.m. Festival tasting tickets are $45, while spectator admission for the tournament is $6. 

1215 Mariners Way, Mission Bay

San Diego Crawfish Boil at Waterfront Park

May 17

For the 36th time, the LSU Alumni of San Diego will stake their claim for the world’s biggest crawfish boil this Saturday at Waterfront Park with the annual 21-plus San Diego Crawfish Boil. There will be live music from the Rebirth Brass Band, unlimited beverages, and 20,000 pounds of hot and spicy Louisiana crawfish served with corn and potatoes. Tents for LSU alumni open at 10 a.m. and standard tables open at 11 a.m. Single tickets are $97 while 10-person tables are on sale for $882 on Eventbrite

1600 Pacific Highway, Embarcadero

Fun things to do in San Diego this weekend May 14-18, 2025 featuring  Willie Nelson performing at the Outlaw Music Festival at North Island Credit Union Ampitheatre
Courtesy of Outlaw Music Festival

Concerts & Festivals in San Diego This Weekend

Outlaw Music Festival at North Island Credit Union Amphitheatre 

May 15

For its 10th anniversary tour, the Outlaw Music Festival will bring legendary artists, talented up-and-comers, and the outlaw spirit to San Diego this Thursday. The lineup for the festival’s local stop features a wide range of talents in country, folk, and Americana, with Willie Nelson & The Family, Bob Dylan, Billy Strings, Sierra Hull, and Lily Meola set to take the stage of the North Island Credit Union Amphitheatre. Tickets start at $46 for this concert, beginning Thursday at 4 p.m.

2050 Entertainment Circle, Chula Vista

San Diego Wonderfront Arts & Music Festival 2025 event lineup

Wonderfront Festival

May 16–18

Headliners for this year’s Wonderfront Festival, a three-day musical party starting this Friday at Embarcadero Park North, include Peggy Gou, Khruangbin, Anderson .Paak & The Free Nationals, and San Diegan Jason Mraz. Other performers to check out include a variety of R&B luminaries (Baby Rose, Jordan Ward), indie darlings (Magdalena Bay, Orion Sun, Vacations) and can’t-miss local acts (Helena Holleran, The Diz, Saint Luna, Three Legged Dog). Tickets start at $165 for single-day general admission and top out at $899 for three-day VIP. 

400 Kettner Boulevard, Embarcadero

Goldenpalooza

May 17

The Golden Hill neighborhood is coming together for the inaugural Goldenpalooza, a free music and arts festival happening Saturday from 11 a.m. to 5 p.m. at Golden Hill Recreation Center. Attendees can check out live music from local bands and youth performers, a silent auction, live artist demos, interactive art installations, and a makers’ market. There will also be booths from community orgs, food vendors, and a range of premium activities. Art experience passes, which come with five premium activity stamps, are $25, with proceeds benefiting the Golden Hill UTK-8 dual immersion school.

2600 Golf Course Drive, Golden Hill 

LOUIS: A Silent Film with Wynton Marsalis and Cecile Licad at Balboa Theatre

May 18 

LOUIS: A Silent Film is a love letter to jazz, inspired by its beginnings in New Orleans and the upbringing of the genre’s most celebrated artist, Louis Armstrong. This Sunday at the Balboa Theatre, classical pianist Cecile Licad, trumpet virtuoso Wynton Marsalis, and an 11-piece jazz ensemble led by conductor Andy Faber will provide a live soundtrack to a screening of the film. A prelude interview hosted by Robert John Hughes will precede the show. Tickets range from $71 to $134 for this live performance. 

868 Fourth Avenue, Gaslamp

Fun things to do in San Diego this weekend May 14-18, 2025 featuring the San Diego International Fringe Festival performers on a theater stage
Courtesy of San Diego International Fringe Festival

Theater & Art Exhibits in San Diego This Weekend

The Counter at the MOXIE Theatre

May 14–June 1

Meghan Kennedy’s The Counter will open Wednesday at the MOXIE Theatre in a new production directed by Desireé Clarke Miller. At an ordinary New York diner, waitress Katie and regular customer Paul build camaraderie that deepens and grows as they begin to divulge close-kept secrets and grief-fueled feelings. General admission tickets range from $20 to $53 for The Counter.

6663 El Cajon Boulevard, Rolando

Theater performers at an event at the 2025 San Diego International Fringe Festival

Taste San Diego: Filipino Culinary Journeys Opening Reception at San Diego History Center

May 15

Feast your eyes on the San Diego History Center’s Taste San Diego: Filipino Culinary Journeys. The exhibition’s second installment opens with a reception this Thursday from 6 to 8 p.m. Taste San Diego tracks the evolution of Filipino cuisine in San Diego from family recipes to contemporary culinary leaders, with a fluid menu of Filipino food and beverage offerings from local vendors. Reception tickets for the general public are $10 and attendees will get to enjoy light hors d’oeuvres, with beer and wine also available for purchase. 

1649 El Prado, Balboa Park 

San Diego International Fringe Festival

May 15–25

The annual San Diego International Fringe Festival, back for year 13 beginning Thursday, brings together eclectic artists from all over the world for more than 230 performances spanning from Pacific Beach to Lincoln Park. Ticket options include individual passes ($13) as well as passes for three ($35), five ($55), and ten ($104) shows, with 100 percent of sales going to the festival artists after a one-time, $7 festival fee. 

Citywide 

Romeo et Juliet at Balboa Theatre

May 17

The San Diego Ballet is resurrecting a fan favorite with two performances of Romeo et Juliet. Artistic Director Javier Velasco’s wistful retelling of Shakespeare’s star-crossed romance Romeo et Juliet channels the feeling of forbidden love with intimate, entrancing choreography. There will be performances of Romeo et Juliet at 2 p.m. and 7:30 p.m. this Saturday at the Balboa Theatre. Tickets start at $48 for this production. 

868 4th Avenue, Gaslamp

Jaja’s African Hair Braiding at La Jolla Playhouse 

May 17–June 15

The 2025–26 season at La Jolla Playhouse kicks off Saturday with Jaja’s African Hair Braiding, which follows a group of West African immigrants working in a Harlem salon. Jocelyn Bioh’s Tony Award–winning comedy takes place on a summer day at Jaja’s African Hair Braiding, a communal space for hair care, gossip, and essential bonds built on the sacrifices of its employees. Tickets range from $30 to $80 for Jaja’s African Hair Braiding

2910 La Jolla Village Drive, La Jolla

Fun things to do in San Diego this weekend May 14-18, 2025 featuring  Fit Athletic's free yoga class at the  Rady Shell
Courtesy of AllEvents

More Fun Things to Do in San Diego This Weekend

Nat at Night 

May 16

During Nat at Night, the San Diego Natural History Museum stays open late with half-priced admission, special food and drink offerings from Wolf in the Woods and The Craft Taco, and a chance for a self-guided tour of the entire museum from 5 to 10 p.m. Adult admission is $12 and can be purchased online or at the door.

1788 El Prado, Balboa Park

San Diego Padres vs. Seattle Mariners at Petco Park 

May 16–18 

As the Padres enter mid-May, they are firmly on pace with the Dodgers, thanks in part to a resurgent season from Gavin Sheets, Luis Arraez’s incredibly low strikeout numbers—à la Tony Gwynn—and MVP-worthy playing from Fernando Tatis Jr. However, the team’s consistency has come from excellent pitching, with a shutdown bullpen anchored by Robert Suarez (aside from Monday’s meltdown against the Angels) and a sturdy rotation led by the reliable arm of Michael King. Friday through Sunday at Petco Park, the Friars will conclude a week-long homestand with a series against the Seattle Mariners, the current favorites to capture the AL West. Tickets for this series start at $38. 

100 Park Boulevard, Downtown

Fit Athletic Yoga at The Rady Shell 

May 17

Begin your weekend with an outdoor workout at a free Bootcamp Yoga class led by local instructor Viktoria Talbot on the grassy lawn of The Rady Shell this Saturday at 9:30 a.m. Taking place every third Saturday, his monthly event from Fit Athletic offers a scenic and rewarding hour-long workout by the bay. Be sure to bring a yoga mat, sunscreen, and water. Space is limited but spots remain available; RSVP here

222 Marina Park Way, Embarcadero

26th Annual Secret Garden Tour of La Jolla

May 17

Wondering what botanical beauties lie behind the gates of La Jolla’s most scenic homes? See for yourself this Saturday with the La Jolla Historical Society’s Secret Garden Tour, an excursion that takes guests into six of the area’s private gardens and includes live music, plein air art, and tabletop designs from local florists and designers. Take the self-guided tour from 10 a.m. to 4 p.m. ($55; $65 day of) and check out the free Secret Garden Tour Boutique, featuring handcrafted items, plants, and vintage finds at the La Jolla Historical Society Wisteria Cottage.

La Jolla

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