Entertainment & Events

This Weekend in San Diego 10/18 – 10/20

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Another fall weekend in San Diego is approaching, so take in some time to enjoy everything this city has to offer and create some new memories with your friends and family. With beautiful fall weather on the horizon, experience everything from wine events to Halloween festivals, to concerts, and more – there is something for everyone to enjoy this weekend!

Friday, October 18

Clairo at House of Blues

20-year old American singer-songwriter, Clairo will be performing at the House of Blues as part of her Immunity Tour. Known for her bedroom pop tracks, Clairo rose to fame after her debut single, “Pretty Girl” went viral in 2017. Tickets start at just $72.35; the show begins at 7 pm.

Photo by Vishnu R Nair on Unsplash

Claudia Oshry

Claudia Oshry Soffer is the creator of the breakout Instagram account @girlwithnojob. Oshry, 24, is a former New York University student who’s made a career on social media about not wanting a job. She’s amassed a female-millennial-skewing audience of more than 4 million followers online, including 4 million on Instagram. She’ll be making a stop in San Diego’s Balboa Theater as part of her Dirty Jeans tour. Tickets are $30.

San Diego Gulls Hockey Game

Hockey is back! The San Diego Gulls will hit the rink on Friday night against Stockton Heat at 7 pm for their first home game. $2 bud lights will be offered at the game all night long. Starting prices for tickets are going for $21. Support your local hockey team at the Pechanga Area this Friday night!

Chris Brown – Indigoat Tour

Grammy Award-winning singer, Chris Brown will take the stage this Friday night at 6:30 pm in the Viejas arena at San Diego State University. Have a fun night dancing and singing along to the prince of Hip Hop and R&B. Tickets starting price is $63.50.

The Princess Bride at Rooftop Cinema Club

TGIF! Whether its date night or a night out with friends/family, enjoy San Diego’s beautiful skyline while watching a movie atop the Manchester Grand Hyatt. Catch The Princess Bride playing at 7 pm or get spooked by The Conjuring at 9:45 pm. Enjoy craft cocktails, popcorn, and all sorts of snacks during the show. The price for a general admission ticket and or known as lounge seat ticket is $17.

Hocus Pocus Movie Screening in the Park

Grab your warm fuzzy blankets and cozy up on the lawn for a screening of Hocus Pocus at Flinn Springs County Park in El Cajon. Pre-movie activities include a bounce house and Halloween craft table for the little ones to enjoy. The showing begins at 5 pm. This is a free event open to the public, dogs are allowed but must be on a leash.

Saturday, October 19

Hallo-Wine Festival

Get ready to sip and swirl at the 12th Annual Hallo-Wine Festival! From 3-6 pm enjoy complimentary wine and hors d’oeuvres for $60 in Balboa Park. This event is held every year in support of raising funds for the National Domestic Violence Charity. There will be an array of boutique wines, hand-crafted beers, spirits, a silent auction, and live entertainment.

Pumpkin Plunge

The pumpkin plunge is back at the Alga Norte Aquatic Center! Bring your swimsuit and enjoy fun pool activities, games, prizes, and floating obstacles. Admission is $10 per person and children under 3 are FREE. The event starts at 5 pm; movie will begin at dusk.

The Capitol Steps

The American political satire comedy group, The Capitol Steps, will perform at the Balboa Theater at 9 pm. The group will have song parodies along with a short skit. Tickets start at $31.50.

The Bahia Fest

Located at the Embarcadero Marina Park North will be San Diego’s Bahia Fest featuring live music from Cultura Profetica, Ramayana, and Alborosie. The event is from 12 – 10 pm with tickets starting at $60.

Villains In the Village

Experience a night full of eerie encounters and spooky times at the Villians in the Village from 4- 9 pm. Enjoy bites, boos, candy, and flavorful potion on Third Avenue in Chula Vista. Alter ego prizes will be available to whoever has the best creative costume. $20 for adults and $10 for kids.

San Diego Alzheimer’s Walk

Join 3,000 San Diegans this Saturday in support of raising funds for Alzheimer’s and dementia. The walk will begin at 8 am and you can either register with a team or individually.

Bernardo Winery Fall Arts and Crafts Fair

The 42nd Annual Fall Arts & Crafts Fair is back this weekend at the Bernardo Winery. The FREE two-day event will feature over 125 vendors of Southern California’s finest jewelry, soaps, paintings and sculpture, local honey, clothing, pottery, items for the home and garden and much more.


Calling all craft beer lovers! Karl Strauss Brewing Company is hosting Collabapolooza, featuring 40+ independent breweries in San Diego. The event is from 1-5 pm in North Park. Tickets are $40 for general admission which includes a tasting glass and unlimited 2oz pours.

Sunday, October 20

Boots in the Park

Dig out those country boots and grab your flannel for a day full of country music down at the Waterfront Park from 12-10 pm. The Boots in the Park event will feature top country singers in the U.S including Cole Swindell, Dylan Scott, and Cassadee Pope. General admission is $59; this is a 21+ event.

Uncork and Unwined

Calling all yogis! The Spa at The Inn at Rancho Santa Fe is hosting their monthly Uncork and Unwind yoga class with a wine tasting. This event is intended to bring the community together for an afternoon of rejuvenation and recharging. Namaste!

Art in the Garden

Art in Garden, presented by MAGEC, is a diverse art show featuring many talented local and SoCal artists. The show is located in the Heritage Garden in Escondido and will begin at 9 am. Stroll through the garden, listen to live music, shop and participate in interactive art booths for children to enjoy.

Young Frankenstein

Cinema Under the Stars, hosted in Mission Hills will be showing the Young Frankenstein at 8 pm. The venue includes single and double zero gravity recliner chairs, love seat cabanas, and a deck chair with a table. Rain or shine, this venue has a retractable covering, blankets, space heaters and all the amenities to keep you warm.

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