11 Things To Do in San Diego This Weekend: May 25-29

It’s finally fall, and although it may not feel like it (our ceiling fans are this close to flying off their hinges), San Diego is ringing in the cozy season with a heap of fun events. Whether you’re wanting to find your new favorite outfit at Fashion Week, cheer at the Oceanside Shock’s home debut, or practice meditation at the Strength in the City Festival, these are the best things to do in October.

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

Concerts & Festivals in San Diego This Month

3

Go beyond the menu during the Taste of North Park, with over 50 food samples and 15 beverage stops, plus live music and art-driven programming to keep all the senses engaged.

7

Cross the Coronado Bridge—and bring your appetite—for A Taste of Coronado, an island-wide culinary jaunt in support of beloved businesses and the Promises2Kids nonprofit.

Theater & Art Exhibits in San Diego This Month

10/8–11/1

In the Roustabouts Theatre Co.’s newest comedy at Scripps Ranch Theatre, roommate beef has no age limit. In “Ripcord,” a feud between Abby and Marilyn escalates to absurd heights.

10 & 11

Pay it forward to local public schools with each pet adoption, purchased piece of art—from over 170 artists—and sip of wine, beer, or spirits at the free La Jolla Art & Wine Festival.

17

Those in search of creativity and community can find both at Other Places Art Fair South, a free showcase for independent artists and galleries at California Center for the Arts, Escondido.

More Fun Things to Do in San Diego This Month

9/30–10/4

Where can you play pickleball with celebs, sample local eats (including that place you’ve always been meaning to try), and take part in the scenic and delicious Grand Tasting at Surf Sports Park? There’s only one answer: the Del Mar Wine & Food Festival.

2–4

Sashay your way through the 19th annual Fashion Week San Diego, home to stunning runway couture, fall designer collections, and a trunk show—perfect for shopping for your new look.

9 & 10

Dance to Y2K throwbacks all weekend long during Ocean Beach Oktoberfest, which includes a beach party, a stein-holding competition, a brat-eating contest, and for VIP attendees, a custom “OB2K Oktoberfest” liter
mug.

10

First comes the sting, then comes the shock. San Diego County’s newest sports franchise, Oceanside Shock, will make its home debut in the Federal Prospects Hockey League versus the Fresno Falcons at Frontwave
Arena.

24

Working out is just one part of this Waterfront Park wellness experience. Practice meditation, play bingo, and recover with sauna zones during the Strength in the City Festival.

25

At the 25th annual Oceanside DÍa de los Muertos Festival, the Day of the Dead is alive and well. Walk through a chalk cemetery and Por Siempre Car Club’s decorative trunk altars during the free event.

At Del Mar Wine & Food Festival’s Grand Tasting, the walk between food tents can take a while. You might stop to watch a chef competition, get pulled toward the DJ, or find yourself playing mini golf before you remember which bite you were after.

Across the Del Mar Polo Fields, there’s also line dancing, a 1961 red Beetle ready for photos, and an aviation-themed pop-up with Reno Tahoe chefs and mixologists. Need a slower stretch? Check out the wellness stops or browse the shops. Here’s what to look for as you make your way through the festival’s zones:

VIP First Bites & First Sips

VIP ticket holders get a head start, with the VIP Reception running from 11:15 a.m. to 1 p.m. and serving first bites, first sips, and a few surprises before the Grand Tasting officially gets going. Champagne Telmont will make the festival’s first pour, while Cohn Restaurant Group brings carajillos alongside pours from Karl Strauss, Licor 43, Tap Truck San Diego, Bebemos Tequila, and Devil’s Grin Gin.

The bites are just as good. Celebrity chef Beau MacMillan will serve a first bite, while Warung RieRie is bringing one of its highly coveted dishes. Yes, this is the restaurant that currently has an eight-month waitlist. You’ll also find bites from The Shellfish Affair, The Waverly, Wolf in the Woods, Dora Ristorante, Cori Pastificio Trattoria, An’s Gelato, Pacific 333, Vintana, and more.

And because every good first act needs a soundtrack, there will be live painting and music, with Courtney Govan bringing live jazz to the reception. It’s the perfect opening act before the main event.

Live Cooking & Culinary Moments

During the VIP Reception, chefs Tommy Gomes and Jeff Roberto will conduct a live ahi cutting. Plant Paradise brings another culinary angle, with celebrity chef Zuliya Khawaja joining the plant-based lineup. The area combines chef talent with plant-forward restaurants and brands, giving guests a chance to see just how creative plant-based cooking can get.

Throughout the weekend, The Stage keeps the cooking demonstrations coming, with celebrities and chefs sharing techniques, recipes, and plenty of inspiration for anyone who plans to actually cook something when they get home. Before you know it, you’re watching a chef demo, casting your awards vote, and sipping mezcal on the grass with friends you just met in line.

DJs, Music, & The Party

At the Grand Tasting, dancing just sort of… happens. A DJ drops the right song. Someone’s holding a taco in one hand and a glass of wine in the other. The country zone breaks into a two-step. Friends convince friends. Strangers become temporary dance partners. By the end of the day, everyone’s forgotten they were ever worried about looking cool.

DJ TENAX will be spinning in Plant Paradise, bringing house, techno, and UKG to an open-air dance floor that’s hard to leave. Chris Cantore, a veteran San Diego broadcaster, takes over the VIP Tent, while BootScootin Line Dance and PVO Events bring country-style line dancing to the Polo Fields, so you can work off your tasting itinerary one two-step at a time.

Then a live guitar hum in the distance leads you to a fuchsia boa over at the Pride Zone, where you’ll find yourself covered in sequins and having the lawn party of a lifetime.

Sports, Tailgates, & Games

Not every activity at the festival requires a tasting glass (although it’s certainly encouraged).

The Matchday Experience brings San Diego FC and San Diego Wave FC into the Grand Tasting, complete with interactive tents and plenty of game-day energy. Athletic Brewing is also sharing activation space with San Diego Wave FC, bringing a fun nonalcoholic option into the mix.

For golf fans, the Los Angeles Golf Club is bringing a Dryve Box golf simulator to the festival. And if your competitive streak is less fairway and more miniature windmill, SD Pop Up Mini Golf has you covered.

The Beach Zone gets in on the action, too, with surfing-inspired elements and Playavole paddle courts. Hemlock Hats and other California brands add to the coastal atmosphere, but the real draw is having somewhere to actually play. And don’t worry, you can cool down in COOLA’s turquoise beach chairs, too, and when your bestie suggests reapplying sunscreen, obviously you do. Basically, there are plenty of ways to work up an appetite between tastings.

Photo Ops & Instagram Moments

You’re going to want to take photos, and the festival has made that extremely easy.

A Timeless Day is bringing multiple photo moments to the Grand Tasting, including a 1961 red Beetle at The Italian Getaway and a teal VW bus in The Beach Zone. For something a little more polished than the standard group selfie, head to the Locals Zone for Pixster Photo Booth and San Diego’s version of a Glam-Bot, complete with a grass red carpet.

Bebemos Tequila is also bringing back its festival-favorite hidden speakeasy. If there’s ever a time for a photo, it’s here. Otherwise, people might not believe you. The speakeasy serves bone marrow shots straight from the bone, with candlelight, a lounge area that makes it hard to believe you’re in a tent outside, and little orange shot glasses. This is “first slide of your festival photo dump” material.

You can also grab your squad and head to LaCroix’s bright and ridiculously cute setup, or swing by San Diego Magazine’s area, where you might stop for a photo in front of the larger-than-life SD Magazine sign and find yourself watching a painting come to life.

But really, you’re in Del Mar. The ocean is essentially your backdrop, and every zone gives you an excuse to stop for the obligatory “totally candid” photo. And yes, the best strategy is to get the group shot before everyone has been sampling wine for three hours.

Shop, Browse, & Take Something Home

The Grand Tasting also doubles as a little shopping excursion, with local makers, fashion, vintage finds, jewelry, and lifestyle brands scattered throughout the grounds. Smoke Revival Vintage Vault brings the thrill of vintage treasure hunting, while Nortte Hats and Hemlock Hat Company make a pretty good case for leaving with a new accessory.

Keep an eye out for jewelry and creative vendors, too, including Iris Studio Jewelry and New Nightfall Jewelry, plus local artists and makers featured throughout the festival. 

You can come for an all day food and wine festival, but still leave with something shiny you definitely did not plan to buy.

Wellness & Reset Moments

We know, at some point, even the most dedicated grazer has to come up for air. The Novo Dia Wellness Zone is designed for exactly that, bringing together mocktails, coffee, hydration, wellness brands, and even bites from Parakeet Cafe.

Step away from the food and drink frenzy for a few minutes, relax in the shade, try some skincare, stretch with prAna, and maybe grab some Instant Hydration Electrolytes before round three.

There’s also nothing wrong with stopping to smell the roses at Green Air Botanicals while devouring a dairy-free cheese dip. It’s less about disappearing from the party and more about making sure you have enough energy to keep going.

The zones give you somewhere to wander, and the activities give you a reason to keep going. So grab your tasting glass, check the schedule, and leave a little room in your afternoon for something you didn’t plan on doing. At Del Mar Wine & Food, that’s usually where things get interesting.

At Del Mar Wine & Food Festival’s Grand Tasting, everyone has their own goals for the day. One friend wants oysters and Champagne. Another heard there’s line dancing. Someone disappeared into Taco Alley. The food person is making a beeline for every chef demo, the golf friend has found the simulator, and someone else is already settled into a beach chair with a mezcal cocktail and has announced they’re “never leaving.”

Consider yourself zoned in.

This year, the Grand Tasting turns the Del Mar Polo Fields into a full-blown foodie wonderland, with chef showdowns, wellness escapes, art installations, lawn games, music, and plenty of magazine-worthy plates. But the zones are where everyone gets to play their own way. You might sip your way through the SLO Zone, accidentally spend the afternoon behind the DJ booth in Plant Paradise, or live out your best beach day in The Beach Zone.

With 100-plus chefs and restaurants, 150-plus wineries, breweries, distilleries, and drink makers, plus a whole lot more happening in between, there’s no shortage of ways to spend the weekend. And with the Grand Tasting taking place October 3 and 4, there’s actually time to explore.

Because the problem with bringing your favorite people to an adult playground is that everyone wants to play differently. Luckily, you get two days to figure it out. Here’s where to start:

The Beef Experience

The Beef Experience, presented by Brandt Beef – One World Beef, is for the people who believe a food festival is a perfectly reasonable excuse to build an entire afternoon around meat. Brandt Beef brings its signature fare to the Polo Fields alongside a seriously stacked lineup of local favorites, from Tanner’s Prime Burgers and Ranch 45 to Jimmy’s Famous American Tavern, Order Fire Barbecue, Flying Pig Pub & Kitchen, The Pit BBQ, Aloha Rib Shack, and more.

And then there’s the tent you might almost miss.

Tucked into Brandt Beef Alley, Bebemos Tequila has set up what looks, from the outside, like a fairly unassuming tent. Walk inside, though, and you’ll find a full little speakeasy lounge, complete with a bar and one very dramatic tequila trick. The team lights the shots right in front of you before pouring them straight into guests’ mouths. Candlelight, fire, tequila, barbecue. Suddenly, your casual afternoon tasting has taken a turn.

Grab a plate of Brandt Beef tallow fries, chase it with a pour from Bebemos Tequila or Tap Truck San Diego, and maybe browse Nortte Hats while you recover. The rules are simple: follow the smoke, trust the grill, and maybe don’t make dinner plans afterward.

The Beach Zone

For the friend who thinks every good afternoon should involve a little sunshine, a cold drink, and nowhere to be, there’s The Beach Zone. Presented by Reef Lifestyle, this laid-back corner brings the San Diego summer fantasy to the Polo Fields, complete with coastal bites, beach-inspired brands, and plenty of reasons to stay awhile.

Grab bites from Duke’s La Jolla, Jake’s Del Mar, Lofty Coffee Co., Dang Brother Pizza Co., and Coral Del Mar, then cool off with Summer Club, Volley, Surfside Iced Tea and Lemonade + Vodka, Tito’s Handmade Vodka, Mezo Mezoritas, Roseade Wine Spritzer, Pinkys, and more. Hemlock Hat Co., Coola, Sambazon, Playavole, Shibumi Shade, Spritz del Conte, and Out of the Woods add a little retail therapy to the mix, because the Grand Tasting obviously needs shopping, too.

And yes, there’s a photo op. Find the teal VW bus from A Timeless Day, gather your favorite people, and pretend you’ve spent the afternoon cruising the California coast instead of wandering around a wine and food festival.

It’s an area filled with surf-inspired games, your next favorite beach accessory, and a drink in hand. Basically, San Diego summer, condensed into one very convenient patch of grass.

Pride Zone

Neon boas, glitter-filled drinks, and enough food to make choosing a single dinner impossible. The Pride Zone presented by San Diego Pride is bringing the energy, gathering some of San Diego’s favorite restaurants, bars, breweries, and sweet spots in one very colorful corner of the Polo Fields. Expect bites and beverages from Cary Q Wines, Gossip Grill, Rootdown & Es Okay, T’Maro Brands, and more.

Plant Paradise

Plant Paradise is your green oasis, but don’t expect it to be particularly peaceful. DJ Tenax returns with house, techno, UKG, and the kind of set that can turn a quick stop into an hour on the open-air dance floor. As Green Air Botanicals sets the mood, grab a cocktail from Mission Craft Cocktails, Makku, or San Hagen Tequila, and a bite from the sprawling lineup of plant-based bites and snacks from some of San Diego’s vegan favorites.

Kindred, Nourish Eats, The Plot, Maya’s Cookies and more. There’s also a full lineup of brands to snack your way through, including Aficio 22, Bücha Hard Kombucha, Nichols Farms, Nuts For Cheese.

Fall Arts Preview presented by SDFC Playmakers

September

Cecil Beaton’s Fashionable World

Museum of Photographic Arts at the San Diego Museum of Art

Now through Jan. 10, 2027

Sift through over 200 photographs, sketches, letters, and costumes from “The King of Vogue,” who photographed World War II, modernized royal portraits, and created the aesthetic for 1920s socialites in London.

Washed Ashore: Art to Save the Sea

Natural History Museum

Now through Feb. 28, 2027

Walk through an 18-foot whale ribcage (and a couple dozen other marine-creature sculptures) made entirely of plastic bottles, flip-flops, lighters, rope, and other plastic detritus found on the beach in the Nat’s 3,000-square-foot second-floor gallery.

Forging a Legacy: 15 Years of Landmark Acquisitions

San Diego Museum of Art

Now through May 31, 2027

Part of SDMA’s centennial, “Forging a Legacy,” highlights artists from the past (Picasso, Monet) and modern day (Hugo Crosthwaite) who contributed to the museum’s collection.

ZWO Astronomy Photographer of the Year

Fleet Science Center

Now through 2027

See the stars (without the smog) at their best from the winners of the world’s largest astrophotography competition—all in the Fleet Science Center’s new basement gallery, specifically dimmed to let the cosmos shine.

Begin Again

The Old Globe

Sept. 6–Oct. 11

From the 2013 silver screen to this year’s The Old Globe stage, you can “Begin Again” (again) with a world-premiere musical adaptation featuring new songs—courtesy of Train—and a story overflowing with hope.

Dear Evan Hansen

Cygnet Theatre

Sept. 9–Oct. 4

“On the outside, always looking in…” marks the emotional crux of the Tony-, Grammy-, and Emmy-award winning musical coming to the Cygnet Theatre.

Kumeyaay Comics by the Kumeyaay Visual Storytelling Project

Museum of Us

Opening Sept. 12

Learn the history of the Kumeyaay Nation from the perspective of the members themselves in an immersive exhibit inspired by graphic novels “Our Past, Present, and Future,” and “Beyond Gaming.”

Good Night, Oscar

North Coast Repertory Theatre

Sept. 16–Oct. 11

During Oscar Levant’s appearances on “The Jack Paar Show,” he explained his reality with mental illness—the institutionalizations, electroshock therapies, nothing was too taboo for him. “Good Night, Oscar” takes us backstage in the raw moments before his 1958 television appearance.

Visiones Nocturnas: Queer Nightlife in Contemporary Art

Museum of Contemporary Art San Diego

Sept. 19–Jan. 17, 2027

A disco ball isn’t just a disco ball. It’s a symbol of where queer communities can finally exhale and be their fullest selves. “Visiones Nocturnas” uses paintings, sculptures, textiles, performances, photos, and videos from Latin American artists to explore what’s at stake when nightclub lights shut off.

Silent Movie Mondays

Balboa Theatre

Sept. 21, Oct. 26, Dec. 7

Guest organists from across the country will come to the Balboa Theatre to accompany a new silent film for each performance. This year closes out with The Headless Horseman (1922), Dr. Jekyll & Mr. Hyde (1920), and a holiday triple feature of Laurel and Hardy films.

Oh, Mary!

Civic Theatre

Sept. 29–Oct. 4

“What if Abe’s assassination wasn’t such a bad thing for Mary Todd Lincoln?” was the question that inspired Cole Escola’s play “Oh, Mary!” In the production, Mary Todd desperately tries to return to the cabaret stage, but her husband (President Lincoln in the midst of the Civil War) keeps getting in the way.

October

Payare Leads Strauss’ A Hero’s Life

Jacobs Music Center

Oct. 3–4

Conductor Rafael Payare opens the San Diego Symphony’s 2026-2027 season with a three-part concert featuring composers Sofia Gubaidulina, Wolfgang Amadeus Mozart, and Richard Strauss.

Emily–No Prisoner Be

Baker-Baum Concert Hall

Oct. 8

Two dozen of Emily Dickinson’s poems are turned into songs—composed by Pulitzer Prize winner Kevin Puts and performed by Grammy-winning mezzo-soprano Joyce DiDonato—for a one-night-only exploration of love, loss, loneliness, and mortality.

Ripcord

The Roustabouts Theatre Co.

Oct. 8–Nov. 1

Roommate beef has no age limit. The latest play from Pulitzer Prize winner David Lindsay-Abaire turns that experience into a comedy through retirement home roommates Marilyn and Abby and the bet between them to see who will break first and move out.

Des Canyons aux Étoiles

La Casa del Zorro

Oct. 12

Composer Olivier Messiaen has chromesthia, so for him, sound evokes a visual connotation. His work “Des Canyons aux Étoiles” brings desert rock and the night sky to mind. See what he means from La Casa del Zorro in the Anza-Borrego Desert, in this performance immersed within nature.

San Diego International Film Festival

Locations Vary

Oct. 13–18

San Diego International Film Festival salutes the silver screen for a 25th time, now with a sixth day adding extra time for parties, screenings, and movie-star tributes.

Rigoletto

Civic Theatre

Oct. 23–25

Considered one of the masterpieces from opera great Giuseppe Verdi, San Diego Opera’s “Rigoletto” sees what happens when the prurient Duke of Mantua and his sharp-tongued court jester become entangled in a fatal curse.

Grim

La Jolla Playhouse

Oct. 27–Nov. 29

When the Grim Reaper’s job becomes too…grim…and he retires after 300,000 years, his daughter picks up the family business. But when she falls for a human and finds beauty in the souls she’s meant to reap, she questions her purpose.

November

Skate Craft

Mingei International Museum

Nov. 21–May 9, 2027

San Diego is nothing without skate culture. Mingei’s “Skate Craft” portrays skateboarding as “living folk art” via its DIY roots (skateboards built in garages) and shows how that ethos shapes the future.

People remember the first time they see Joe Dreamz.

Mine was a mile into the 2023 Carlsbad Half Marathon. He was standing on a speaker in the middle of the course, singing: “Hey you with the shoes, are you living Joe Dreamz?” Clearly not. I’m running uphill at 7 in the morning, I thought.

Months later, walking out of The Rady Shell, there he was again—parting the crowd of concertleavers Moses and the Red Sea style, singing the same song: “Hey you with the purse, are you living Joe Dreamz?”

Who’s this man at every public spectacle, singing metaphysical questions in a hand-altered, color-coordinating suit that would make James Brown proud and standing on a Soundboks speaker with a microphone and tip bucket?

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A few years ago, San Carlos–born, El Cajon–based Joe Dreamz wasn’t exactly living Joe Dreamz—making $5 footlongs at Subway, dealing with croissant coworkers at Costco’s bakery, and selling life insurance. After he got let go from the life insurance gig and his car broke down in the middle of a 2020 road trip in Seattle, he used his emergency savings to buy a microphone and a speaker; a self-taught musician, he pulled from the only skillset he knew to monetize. He’d set up at Seattle’s Pier 55 and ask people what their dreams were. Then, for $5, create a freestyle rap to commemorate (and hopefully activate) those dreams.

“The goal is that someone listens to a Joe Dreamz song, and they don’t have to wait until metaphorically their car breaks down before they chase their dreams,” he says.

A chance encounter with an airport worker led to a free flight back to San Diego, and Joe Dreamz came home “transformed,” he says. He started busking at the Mission Beach boardwalk, Kate Sessions Park, outside Gaslamp bars; then Padres games, farmers markets, marathons. He also hit the mic outside of Coachella this year (“Joe-chella,” he says).

It’s not a get-viral-quick gimmick; people’s lives are changing. One fan finished writing her book after a dose of Joe Dreamzpiration. Another named his own daughter Joy Dreams.

Now, he’s working on the upstart “Tell Me Your Dream” podcast and DREAM Week in local schools, where each day represents a step toward achievement (D is destination day, R is reason day…). He doesn’t want inspiration to reach you only after hearing a song or watching a video: He believes in this message so much that he literally got DREAM tattooed onto his forehead.

“It’s on my face, so people have no choice [but to see it],” he says. “I’m a local celebrity here, so everywhere I go, people ask me for pictures. In every selfie, the message goes along for the ride too.”