Where to Go on a Date in San Diego This Fall

From speakeasies to music festivals, movie screenings, and more, these date ideas are sure to impress.

Near-perfect weather and practically limitless activities ranging from entertainment to adventure are at the top of the list of reasons why we all love living in San Diego. We’ve got scores of sparkling beaches, an award-winning brewery scene, and plenty of picturesque hikes to remind us why it’s called America’s Finest City. But our wealth of options also makes planning date night especially challenging. To help you narrow down the selection, we’ve rounded up the very best the city has to offer, whether you’re looking for a casual hang, an impressive first date, or a grand celebration. Here are our favorite things to do and places to go with someone special this fall:

Pacific Beachfest
Pacific Beachfest

Saturday, October 1
Free-$$
Pacific Beach
As if going to the beach isn’t enough fun, there’s Pacific Beachfest. The day starts early with a half-marathon race at 6:30 am, a volleyball tournament at 9 am, and a 5K race at 10 am. From 11 am to sunset, the festivities will include live music on three different stages, a DJ lounge, a Best of the Beach Fish Taco Contest, the Big Josh Beer Garden with local craft beers, a shape-up social, and vendor booths. The music festival is free to enter, but race registration, beer, and other costs vary.

San Diego Restaurant Week
San Diego Restaurant Week

$-$$$
Sunday, September 25–Sunday, October 2
Various locations
For eight glorious days, nearly 100 eateries all over the county will be participating in the bi-annual San Diego Restaurant Week, making dinner dates out a more wallet-friendly option. There are delicious options for every taste and budget, from diner favorites to white tablecloth steakhouses—restaurant offerings include two-course prix-fixe lunch menus and three-course prix-fixe dinner offerings for $10-60. Use the interactive website to plan your food odyssey, and be sure to make reservations at your favorite participating places early; tables are sure to fill up quickly. And don’t forget—your servers will be extra busy making your date a great experience during SDRW, so thank them profusely and tip as generously as you are able.

La Jolla Art & Wine Festival
La Jolla Art & Wine Festival

Saturday, October 8–Sunday, October 9
Free
La Jolla
Wander hand-in-hand down beautiful Girard Avenue in La Jolla from 10 am–6 pm both Saturday and Sunday to enjoy art and vino while supporting a good cause at the 11th annual La Jolla Art and Wine Festival. The free event will host 150 artists and craftsmen from San Diego and beyond. There will also be a silent auction, live entertainment, pet adoptions, a gourmet marketplace, and a wine and beer garden. All proceeds will go to support the arts programs at local elementary and middle schools. Purchase your tickets for the wine and beer garden (21+ only) online—depending on advance sales, they may not be available at the door.

Walk the red carpet at a film fest

$-$$$$
Various locations
Ditch Netflix for The 21st Annual San Diego International Film Festival and enjoy world-premiere films, never-before-seen studio releases, new and unique independent filmmaking together, as well as elegant parties and up-close and personal events with the filmmakers. Choose from single-day passes, five-day fest passes to all the films, or full VIP passes for access to all parties, screenings, panels, and events, VIP lounges, and more. Or, host your own screening party in the comfort and safety of your own home with the virtual pass, with 80+ features, docs, and shorts that will be available on demand in the Festival Virtual Village for ten days with pre-recorded Q&As.

Early November brings the 23rd Annual San Diego Asian Film Festival, the largest exhibition of Asian cinema in the western United States, featuring West Coast, North American, and world premieres of films from around the world.

Mad Hatter’s Mischief Soirée
Estancia La Jolla

Leave the trick-or-treating to the kids

Free-$$$$
Various locations
San Diegans of all ages love Halloween, and there’s no shortage of places to go and parties to attend. The Haunted Trail at Balboa Park will have you grabbing each other in fright from September 23 through Halloween night; San Diego’s most famous haunted hotel, the Hotel del Coronado, has a full slate of spooky fun planned; and Estancia La Jolla Hotel and Spa hosts their inaugural Mad Hatter’s Mischief Soirée on October 29. The biggest, goriest, creepiest haunted experience in San Diego happens in The Scream Zone at Del Mar Fairgrounds, with horrifying attractions like hallucinatory, zombie-filled Haunted Hayrides, Hell-Billy Hootenanny, The Passage, the most confusing maze you’ve ever set foot in, and the Spirit Lounge bar for after-scare cocktails and cuddling.

San Diego Brewers Guild
San Diego Brewers Guild

Friday, November 4-Sunday, November 13
$-$$
Various Locations
Hopefully you both have plenty of vacation days saved up because this is the best ten days for beer drinking in America’s Finest City. San Diego Beer Week kicks off with events happening at breweries and beer bars all over town, and with over 120 participating breweries, that’s a lot of hop-centered celebrating. Check the SDBW website to get updates on events happening all week long.

Fairweather
Fairweather

Visit a secret bar

$-$$$
Various locations
Everybody loves to be in on a secret, even when it’s not really a secret. There’s just something vaguely clandestine (and a bit naughty) about going into, say, Kilowatt Brewing’s Oceanside tasting room and finding the hidden passageway, where a “space elevator” beams you up to the planet Rillispore and The Space Pad, a 1950’s Atomic Era-styled spaceport. Open a door at the back of Common Theory in Kearny Mesa to visit a futuristic Chinese apothecary, the stunning Realm of the 52 Remedies. Go behind the walk-in refrigerator in Craft & Commerce for tropical libations at False Idol, while Rare Form’s delicatessen leads to a rooftop speakeasy, Fairweather, overlooking Petco Park. Reservations are usually required, so check the website before heading out.

Belly Up
Belly Up

Rock out to live music

$-$$$
Various locations
Nothing beats seeing a live band, but tickets for the big names can get expensive. Fortunately, San Diego’s live music scene is as exciting and diverse as the venues that provide them. The Belly Up in Solana Beach welcomes acts ranging from Saharan folk music to alt-reggae, with a good sprinkling of legendary early rockers from the ‘60s and ‘70s. The Music Box’s three tiers of seating include opera booths with bottle service, two outdoor patios, bars on two levels, and a private VIP skybox overlooking the stage, as well as a menu that includes kobe sliders, charcuterie, flatbreads, and cocktails on tap. See up-and-coming underground alt-rock at the famously divey Casbah, where past guests have included Nirvana and Smashing Pumpkins, or hit Winston’s Beach Club in Ocean Beach for a jam band/reggae vibe.

San Diego Bay Wine + Food Festival
San Diego Bay Wine + Food Festival

$-$$$
Various locations
What’s more romantic than strolling hand-in-hand through one of San Diego’s unique neighborhoods, noshing on all the best sips and bites from local restaurants? In October, explore all that North Park has to offer at Taste of North Park, a self-guided tour of one of San Diego’s culinary meccas, where you can munch on food from over 35 restaurants and sip beverages from more than 12 breweries. Head to North County on October 16 for the Grand Avenue Festival, a 30-year-old Escondido tradition with live music, a beer and wine garden, and the Art in the Garden juried art show.

November brings the West Coast Taco & Beer Festival to Spanish Landing Park, featuring unlimited craft beer tastings from local and regional breweries and dozens of culinary vendors and food trucks selling the best tacos in California. Celebrate 17 years of eating and drinking from November 9–13 at the biggest wine and culinary gathering on the West Coast, the San Diego Bay Wine & Food Festival, where events include The Grand Decant, a tasting with the country’s top sommeliers, wineries, and winemakers, a star-studded Grand Tasting at the Embarcadero Marina Park North on Saturday, with wine and spirit vendors, along with San Diego’s top chefs competing for bragging rights as well as cash and prizes and Taco TKO, the ultimate throwdown where you taste and decide who has San Diego’s best taco. Celebrate the return of Taste of December Nights to Balboa Park December 2-3 and enjoy amazing food while you stroll through the beautiful lights and attractions.

San Diego Museum of Art
Boycez/Shutterstock

Ogle some art

Free-$$
Various locations
Whether your date takes you to Barrio Logan, Balboa Park, Hillcrest, Liberty Station, or almost any other neighborhood, wandering through local art galleries and museums is a must-do for any art lover. Experience Comic Con all year long at the new Comic Con Museum in Balboa Park, where comic art and similar genres are celebrated through rotating exhibits and interactive displays. Elsewhere in Balboa Park, the San Diego Museum of Art is hosting three outstanding exhibits spanning late October through March 2023: Chapel of the Rocks by Justin Sterling (October 29, 2022–February 12, 2023), is an immersive experience of broken and mended stained-glass windows; Lisa Ross: Elegy to a Uyghur Homeland (November 5, 2022–March 5, 2023) poignantly captures the rituals and spiritual traditions of Uyghur shrines and everyday life in and around the Taklamakan Desert captured during the artist’s decade-long travels through the area; and Sergio Hernandez: Embers of Oaxaca (November 12, 2022–February 12, 2023), the first U.S. solo museum exhibition by Oaxacan contemporary artist Sergio Hernandez. It showcases more than 30 large-scale paintings and mixed-media works, some of which will debut to the public for the first time as part of this exhibition.

Ocean Beach MainStreet Association
Ocean Beach MainStreet Association

$-$$$
Various locations
Given our status as a craft beer capital, it’s inevitable that you and your love will find yourself bonding over saisons or sessions at a beer garden or festival. Autumn in San Diego is ridiculously stacked with beer festivals and Oktoberfest celebrations, starting on the weekend of September 30-October 2 with the 49th Annual La Mesa Oktoberfest and the first weekend of the El Cajon Oktoberfest, both are from Friday-Sunday, and North County’s Olivenhain Oktoberfest is only on Sunday, October 2. The weekend of October 7-9 includes the second weekend of El Cajon Oktoberfest, as well as the two-day Ocean Beach Oktoberfest, where your beer comes with a complimentary million-dollar view.

$-$$
University Heights
Introduce each other to the agave spectrum at Cantina Mayahuel, where over 100 different mezcals, sotols, bacanoras, and raicillas line the wall behind the bar. While mezcal margaritas are available (and delicious), aficionados prefer to sip it neat, and the friendly, knowledgeable bartenders will gladly guide you through your tasting experience. If mezcal isn’t your thing, there are also 250+ varieties of tequila, including the house brand, Don Lorenzo Reposado Reserva. Their expanded patio can accommodate in-house drinking and dining on a first-come basis.

Balboa Park
SunflowerMomma/Shutterstock

Explore Balboa Park like a tourist

Free
Balboa Park
Not unlike human relationships, it’s easy to start taking even a treasure like Balboa Park for granted. Renew your love for both with a romantic hand-in-hand stroll through the exquisite gardens and architecture, hike one of the 19 trails, or snuggle through a free afternoon concert at Spreckels Organ Pavilion, held every Sunday at 2 pm.

Windmill Food Hall
Windmill Food Hall

Check out a food hall

$-$$
Various locations
Food halls, the latest trend in casual dining, are a far cry from the old mall food courts you used to hang at back in middle school, plus you can scope out your new crush’s culinary leanings while indulging your own whims. The Sky Deck at Del Mar Highlands Town Center, Market on 8th in National City, the Liberty Public Market in Liberty Station, and the Old Town Urban Market in Old Town host craft cocktail bars and nearly every kind of food shop you can imagine, from pizza to poke.

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Mary Beth Abate is a San Diego-based freelance writer by way of Chicago and Los Angeles. Her hobbies include yoga, pickling and fermenting stuff, reading cookbooks and drinking fabulous gin. Keep up with her experiments @MaryBeth_Abate.