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16 Things to Do in San Diego This Weekend: September 17–21

Enjoy a taste of Gaslamp, sign up for Coastal Clean Up Day, and explore the sounds of the Adams Avenue Street Fair
Fun things to do in San Diego this weekend September 17-21, 2025 featuring Super Girl Surf Pro in Oceanside
Courtesy of Visit Oceanside

The end of summer is nigh, but there’s no need to say goodbye just yet. There are free festivals, theatre world premieres, and plenty of community events to take part in before the autumn equinox arrives on Monday. The Super Girl Surf Pro, ArtWalk Carlsbad, the Adams Avenue Street Fair, and PIFA San Diego will offer ways to engage with the city’s sports, culture, art, and music all weekend long (plus, they’re free to attend). Over in the performing arts category, La Jolla Playhouse (All the Men Who’ve Frightened Me), The Old Globe (Huzzah!), and the Diversionary Theatre (Manifest P*ssy) are opening their doors for exciting new productions. Additionally, San Diegans can volunteer their Saturday morning for environmental preservation at one of more than 100 local cleanup sites in honor of Coastal Cleanup Day. 

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

Fun things to do in San Diego this weekend September 17-21, 2025 featuring Canyon to Coupe at Fairmont Grand Del Mar
Courtesy of Fairmont Grand Del Mar

Food & Drink Events in San Diego This Weekend

Canyon to Coupe at Fairmont Grand Del Mar

September 19

Dine on the Fairmont Grand Del Mar’s outdoor terrace this Friday at 6 p.m. Canyon to Coupe guests will start out with an aperitif before embarking on a five-course, cocktail-pairing dinner with locally sourced ingredients, drinks, and live music inspired by the beauty of the adjacent Los Peñasquitos Canyon. Reservations are $165 per person, plus tax and 20 percent gratuity.

5300 Grand Del Mar Court, Del Mar

Whiskey & Wine at Estancia La Jolla

September 19

Grab a plateful of homestyle cooking to go with samples of whiskey, bourbon, and wine at Estancia La Jolla Hotel & Spa’s 21-plus Whiskey & Wine shindig this Friday from 6 to 9 p.m. Visitors can enjoy live music and unlimited food and beverage experiences from vendors like Whistle Pig Whiskey and Foley Family Wines. Patrons will also receive complimentary valet parking. Tickets are $103 for Whiskey & Wine. 

9700 North Torrey Pines Road, La Jolla

Taste of Gaslamp

September 20

Sample the gastronomy of the Gaslamp Quarter this Saturday from 1 to 4 p.m., with over 20 neighborhood restaurants taking part in the 29th annual Taste of Gaslamp. Foodies can pick up their wristband, map, tasting guide, and some groovy cocktails at the pre-party at Good Night John Boy. After the event, enjoy an outdoor afterparty from 4 to 7 p.m. at Margaritaville’s 5 o’Clock Somewhere Rooftop Bar. Ticket options include general admission ($55; $65 day of) and VIP passes ($80; $90 day of), which come with five extra bites and sips. 

Fourth Avenue and K Street, Gaslamp

Fun things to do in San Diego this weekend September 17-21, 2025 featuring the Adams Avenue Street Fair
Courtesy of Adams Avenue Business District

Concerts & Festivals in San Diego This Weekend

Super Girl Surf Pro

September 19–21

See women surfers shred at Oceanside Pier throughout the free, three-day Super Girl Surf Pro festival. Among those tackling the waves this weekend are competitors from the World Surf League’s Women’s Qualifying Series, including San Clemente native and reigning Super Girl Surf Pro champ Eden Walla. Festivalgoers can also check out roller skating, beach sports, wellness classes, DJ sets, a festival village, and 17 concerts, including performances by Plain White T’s, Lupe Fiasco, and local pop punk band Flailing Idiot.

300 The Strand North, Oceanside

Sacha Boutros: Paris After Dark at The Conrad

September 20

To celebrate the CD release of her new project Paris After Dark, jazz artist Sacha Boutros is embracing a century’s worth of French and American composers at her concert this Saturday at 7:30 p.m. at the Baker-Baum Concert Hall. Boutros will perform the works of Serge Gainsbourg, Cole Porter, Dalida, and more with the help of a Parisian musical ensemble and trumpeter Stéphane Belmondo. Presented by Boutros’ music education nonprofit Sacha’s Supper Club, this performance will officially kick off its new Music Without Borders series. Tickets range from $68 to $98.

7600 Fay Avenue, La Jolla

Pacific Islander Festival San Diego

September 20–21

Peruse Pacific Islander cuisine, entertainment, and craftsmanship at PIFA San Diego, a free weekend-long cultural celebration at Ski Beach. The festival grounds will open at 7:30 a.m. Saturday and Sunday, and attendees can explore unique cultural villages showcasing art and educational materials, a lineup of local PI-led food and craft vendors, and several booths for community groups and nonprofit orgs, plus a car and motorcycle show.

1600 Vacation Road, Mission Bay

Adams Avenue Street Fair

September 20–21

This Saturday from 10 a.m. to 10 p.m. and Sunday from 10 a.m. to 6 p.m., any time is a good time to catch live music. At the Adams Avenue Street Fair, 75 acts will perform across seven stages, with headliners including Strawberry Fuzz, The Schizophonics, Dave & Deke Combo, and Nortec: Bostich + Fussible. There will also be carnival rides; four beer gardens; food vendors; 300 art, craft, and retail booths; a Cool Zone to help beat the heat; and four comedy shows at Adams Avenue Theater. This festival is free for all ages, and VIP pre-sale beer tickets, which come with four craft brews, are on sale for $21 per day. 

Adams Avenue between 32nd and 36th Street, Normal Heights

Fun things to do in San Diego this weekend September 17-21, 2025 featuring Huzzah! at The Old Globe
Courtesy of The Old Globe

Theater & Art Exhibits in San Diego This Weekend

Huzzah! at The Old Globe

Through October 19

It’s only appropriate that a musical that revolves around a renaissance fair is having its world premiere on the Shakespearean stage of The Old Globe. Huzzah!, created by Nell Benjamin and Laurence O’Keefe and directed by Annie Tippe, follows two feuding sisters whose father’s renaissance faire is unexpectedly bestowed upon them. Tickets range from $45 to $141, with nightly performances of Huzzah! Tuesday through Friday and Sunday. On Saturday evening, The Old Globe will commemorate its 90th anniversary with a swanky gala; visit here for more details. 

1363 Old Globe Way, Balboa Park

San Diego potter and ceramic artist Wayne Chapman from Solana Beach and featured in the Mingei's Mid-century ceramic art exhibit Boundless

Les Misérables at Civic Theatre

September 16–21

Romance, redemption, and a fight for freedom are at the heart of this spellbinding musical. Based on Victor Hugo’s novel of the same name, Les Misérables is a fictional ensemble account of 1800s France centered on the journey of escaped parolee Jean Valjean and policeman Javert’s ceaseless efforts to capture him. Tickets start at $39, with eight performances at the Civic Theatre.

1100 Third Avenue, Embarcadero

All the Men Who’ve Frightened Me at La Jolla Playhouse

September 16–October 12

What does it mean to become a parent? Noah Diaz’s All the Men Who’ve Frightened Me, which begins its run Tuesday at La Jolla Playhouse, aims to tackle this question from a unique perspective: Originating from the Playhouse’s DNA New Work Series, the world-premiere production revolves around a trans man’s decision to carry a baby. Tickets range from $30 to $64 for All the Men Who’ve Frightened Me, with six preview performances this week before it officially opens Sept. 23. 

2910 La Jolla Village Drive, La Jolla

Manifest P*ssy at Diversionary Theatre

September 17–October 12

Another world premiere, Manifest P*ssy, will kick off season 40 at the Diversionary Theatre this Wednesday. The theater adaptation of performer, writer, and director Shakina’s one-woman show will take audiences through her trek to Thailand for gender confirmation surgery and feature an original glam rock soundtrack. There will be daily performances of Manifest P*ssy Wednesday through Sunday, with opening night (Saturday) already sold out. Tickets range from $12 to $47 for previews (Wednesday through Friday) and rise to $12 to $72 for all following performances. 

4545 Park Boulevard, University Heights

Social Security at PowPAC

September 19–October 12

A new adaptation of Andrew Bergman’s 1986 comedy Social Security will open this Friday at PowPAC. Social Security follows Barbara and David Khan, married art dealers whose lives are jolted by a surprise entanglement of business and pleasure. General admission is $25 for Social Security, with performances Friday (7:30 p.m.), Saturday (7:30 p.m.), and Sunday (2 p.m.) this week. 

13250 Poway Road, Poway

ArtWalk Carlsbad

September 20–21

ArtWalk San Diego will continue its annual art showcases with a two-day stop in Carlsbad. Perched above The Flower Fields with the glistening Pacific Ocean in the distance, over 150 artists will display and sell their photography, sculptures, paintings, and much more this Saturday from 11 a.m. to 6 p.m. and Sunday from 10 a.m. to 5 p.m. There will also be an interactive KidsWalk, food trucks, two 21-plus beverage gardens, and all-day live music throughout this free festival. 

Armada Drive, Carlsbad

San Diego Dance Theater’s Trolley Dances 

September 20–21

Enjoy a choreography-filled ride on the Green Line throughout the San Diego Dance Theater’s Trolley Dances. Volunteers will lead attendees on a two-hour metro tour, with all six stops featuring a unique dance performance crafted by an acclaimed choreographer, including former SDDT Artistic Director Jean Isaacs. There will be hourly tour times from 10 a.m. to 3 p.m. on Saturday and Sunday, all of which will start and conclude at Fashion Valley Transit Center. General admission is $42 and can be purchased here; kids ages 8 and under can attend for free with a paying adult.

1205 Fashion Valley Road, Mission Valley

Fun things to do in San Diego this weekend September 17-21, 2025 featuring California Coastal Cleanup Day from I Love a Clean San Diego
Courtesy of I Love a Clean San Diego

More Fun Things to Do in San Diego This Weekend

California Coastal Cleanup Day

September 20

Help protect our local bodies of water from pollution this Saturday from 9 a.m. to noon during Coastal Cleanup Day, an international, volunteer-driven environmental initiative. Straighten up the northern shores of San Onofre, head south to the Tijuana River Valley, venture east to Julian’s Volcan Mountain, or sign up for one of the 100-plus other locations organized throughout the county by I Love A Clean San Diego. Be sure to bring gloves, water, and sun protection. Check out the full list of cleanup sites for more details about registration. 

San Diego County 

Dipper Dash 5K 

September 21

Zip through Mission Beach at your own pace Sunday morning in the Dipper Dash 5K. Racers will start and cross the finish line at Belmont Park and receive complimentary goodies (a Ride & Play wristband and a drink ticket) to savor a day of seasonal activities and treats—like pumpkin spice churro fries—at the Beachside Fall Fest. In recognition of Childhood Cancer Awareness Month, this 5K will support Lakeside-based nonprofit Team Parker For Life. Registration is $55 for the 5K and $45 for the Kids Loop, intended for children 10 and under. 

3146 Mission Boulevard, Mission Beach

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.

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