Things to Do in San Diego This Weekend & All October: The Complete Fall Guide
San Diego’s best season might just be the one everyone overlooks. As summer crowds fade, the city settles into what locals call “Second Summer” — warm days, cool nights, and a packed calendar of festivals, family events, and fall traditions. Here’s everything happening this weekend, plus the best of what October has in store.
What is there to do in San Diego this weekend and in October? This weekend brings the Pacific Islander Festival, dragon boat races, and the Little Italy Farmers Market, while October delivers the Del Mar Wine + Food Festival, Julian’s apple season, month-long free admission for kids, and citywide Halloween events — all against some of the year’s best weather.
This Weekend: September 26–27
Pacific Islander Festival (Saturday, September 26, 8am–5pm) — Held at Ski Beach in Mission Bay, this festival celebrates the traditional cultures of Melanesia, Micronesia, and Polynesia through music, dance, food, and crafts — a genuinely unique cultural experience for the whole family.
Dragon Boat Races (Saturday–Sunday, September 26–27) — Also at Mission Bay’s North Tecolote Shores, watch college, corporate, and international club teams compete in dragon boat racing, with a Vendor Village featuring local San Diego businesses on-site.
Little Italy Farmers Market (Saturday, September 26, 8am–2pm) — A weekly Saturday tradition, this certified farmers market brings fresh produce, baked goods, cheese, coffee, and local artisans to the heart of Little Italy — a great low-key morning stop before or after either of the above.
Del Mar Wine + Food Festival (September 30 – October 4)
The county’s biggest culinary week unfolds almost entirely across Del Mar and Rancho Santa Fe this year. Highlights include Rioja Uncorked at Rancho Valencia in Rancho Santa Fe, a Justin Wine Dinner featuring chefs from Estancia La Jolla and Top Chef alumni, a celebrity pickleball tournament hosted by Drew Brees benefiting Feeding San Diego, and the two-day Grand Tasting at Surf Sports Park on October 3–4, featuring hundreds of bites and pours from Southern California’s top restaurants and wineries. Full event details and tickets are available at delmar.wine.
A Day Trip to Julian for Apple Season
An hour and fifteen minutes northeast of the coast, the mountain town of Julian peaks for apple season through October — fresh-baked pies at Mom’s Pies and Julian Pie Company, apple cider straight from the orchards, U-pick farms open on weekends, and fall foliage along the mountain roads on the drive up. The Julian Autumn Jubilee at Fort Cross runs weekends from September 26 through late October, adding a pumpkin patch, hayrides, candle dipping, cider pressing, a petting zoo, and old-fashioned fall activities to the mix.
Kids Free San Diego (All Month)
Now in its 15th year, Kids Free San Diego runs all of October, offering free admission, meals, or hotel amenities for kids 12 and under at over 100 participating venues across the region. A full list of participants is available at KidsFreeSanDiego.org.
Halloween Events for the Whole Family
San Diego takes Halloween seriously. SeaWorld’s Howl-O-Scream runs select nights through October 31 with new scare zones and live entertainment, while HalGLOWeen at the San Diego Zoo lights up the park every Friday through Sunday, October 2–31, with musical entertainment, special performances, and family-friendly festivities. For something more low-key, Balboa Park hosts a Halloween Family Day Out with free museum admission for kids, and Little Italy’s India Street fills with trick-or-treaters visiting local businesses each year.
Late-Season Whale Watching in October
October marks the tail end of San Diego’s humpback whale season, as these massive whales begin their own southbound migration — often accompanied by large pods of dolphins. It’s one of the last good windows before winter’s main event: gray whale season, which doesn’t begin until mid-December and runs through April.
Why Fall Is San Diego’s Best-Kept Secret
Beyond the events, the appeal of October in San Diego comes down to conditions: highs around 75°F, lows in the low 60s, ocean temperatures still swimmable in the high 60s, and virtually no rain. Hotel rates typically drop 30–40% from peak summer pricing, and the crowds that fill the county’s beaches and attractions all summer have largely moved on — making it one of the best times of year to actually enjoy everything the region has to offer, whether you’re visiting or already calling Del Mar or Rancho Santa Fe home.
Frequently Asked Questions
What family events are happening in San Diego this weekend?
This weekend (September 26–27) includes the Pacific Islander Festival at Mission Bay, dragon boat races at North Tecolote Shores, and the weekly Little Italy Farmers Market.
Where is the Del Mar Wine + Food Festival held?
The 2026 Del Mar Wine + Food Festival runs September 30 through October 4, with events across Del Mar and Rancho Santa Fe, including a Grand Tasting at Surf Sports Park on October 3–4.
Is Julian a good fall day trip from San Diego?
Yes. Julian, about an hour and fifteen minutes from downtown San Diego, is known for its apple season through October, with pie shops, U-pick orchards, and the Julian Autumn Jubilee at Fort Cross running weekends through late October.
What Halloween events happen in San Diego in October?
San Diego hosts numerous Halloween events in October, including SeaWorld’s Howl-O-Scream, HalGLOWeen at the San Diego Zoo (Fridays through Sundays, October 2–31), and family-friendly events in Balboa Park and Little Italy.
When does whale watching season start in San Diego?
San Diego’s whale watching calendar shifts through the year — October marks the tail end of humpback whale season, while gray whale season, the region’s most iconic migration, begins in mid-December and runs through April.
What is the best month to visit or explore San Diego?
October is widely considered one of San Diego’s best months, combining warm, dry weather in the mid-70s with lower hotel prices and smaller crowds than peak summer.
Exploring San Diego and thinking about calling it home? Contact the Jason Barry Team to learn more about the neighborhoods that make weekends like this possible year-round.