If you can’t find something fun to do around Northern CA this May, you’re not trying hard enough. But we get busy schedules, so we’ve taken some of the work out of it with this list of can’t-miss events.
This May, Northern CA is hosting a range of unique activities, from a large-scale Wine & Jazz Festival and a Mother's Day flea market to specialized experiences like a NY Deli Pop Up and a thrilling Flamenco Arts International performance.
Whether you're looking for stand-up comedy at a winery or an upscale wine tasting for singles, there are plenty of ways to enjoy the mild spring weather.
When: Sun, May 10, 2026 at 10:00 AM
Where: Irving Street, Irving St, SF, CA, 94122
Details: The Inner Sunset Flea Market, a cherished local tradition held on the second Sunday of every month from April through November, will celebrate Mother's Day on May 10, 2026. Organized with Inner Sunset Park Neighbors, the event transforms two full blocks of Irving Street, between 9th and 11th Avenues, into a bustling open-air market. Visitors can browse a diverse array of vintage finds, handcrafted goods from local creators, and community booths. The market also features live musical performances, complimentary family activities, and direct access to the many distinct restaurants and boutiques throughout the Inner Sunset.
When: Sat, May 9, 2026 at 12:00 PM
Where: Half Moon Bay, CA, 94019
Details: Celebrating its fifth anniversary, the Half Moon Bay Wine & Jazz Festival will take over Historic Main Street on Saturday, May 9, 2026, from 12–5 p.m., offering California wines, jazz, and local food. Hosted by the Half Moon Bay Downtown Association, the festival showcases 50 wineries from regions like Napa and Sonoma, allowing attendees to sample various styles from sparkling wines to reds. Musical director Marcus Shelby curates the premier jazz talent on the Main Stage, complemented by local food trucks and a garden featuring craft ales and ciders. General admission is $68, including a souvenir glass, while $175 VIP passes offer a private lounge; tickets are available at hmbwineandjazzfest.com/.
When: Thu, May 14, 2026 at 5:30 PM
Where: 85 W Portal Ave, SF, CA, 94127
Details: The New York deli pop-up returns to West Portal Avenue at the old Empire Theater on Thursday, May 14. Craving classic, oversized pastrami or corned beef sandwiches on rye with a tangy pickle? This lively neighborhood event is the perfect pre-Mother’s Day outing. Preorders are highly recommended as it sells out quickly!
When: Fri, May 15, 2026 at 5:00 PM
Where: Red Bay Coffee Roastery, 3098 E 10th Street, Oakland, CA 94601
Experience an evening at Red Bay's industrial roastery in Oakland with "The Roastery Unplugged," presented by KQED Live on May 15. This casual event features live soundscapes and professional coffee cupping sessions in the lab, offering a rare after-hours look at the warehouse. General admission is $30 and includes a complimentary caffeinated beverage, while VIP tickets are available for $45.
When: Sat, May 23, 2026 at 4:30 PM
Where: Regale Winery & Vineyards, 24040 Summit Rd, Los Gatos, CA, 95033
The Upscale Wine Tasting/Speed Dating/Dance Party takes place Saturday, May 23, from 4:30 to 8:30 p.m. at Regale Winery & Vineyards in Los Gatos. Attendees can enjoy speed dating, wine tasting, and a dance party for a cost of $55 (advance ticket required), or $25 in advance ($30 at the door) for the dance party only.
When: Sat, May 23, 2026 at 7:30 PM
Where: Presidio Theatre Performing Arts, 99 Moraga Ave, SF, CA, 94129
Flamenco Arts International (FAI) presents the World Premiere of "Songs from a Sinking Ship," a dramatic production telling the story of a ship's crew caught in a supernatural battle for redemption, told entirely through passionate flamenco dance, original music, and immersive performance. The show will run for two performances only on Saturday, May 23, 2026, at 2 p.m. and 7:30 p.m. at the Presidio Theatre. The production has previously earned a Special Award from the Isadora Duncan Dance Awards. Directed by José Maldonado, the cast includes living legend El Torombo and other featured artists. Tickets are available online, ranging from $49–$93.
When: Fri, May 29, 2026 at 7:30 PM
Where: Concannon Vineyard, 4590 Tesla Rd, Livermore, CA, 94550
Details: The Late Pour: Comedy Night at Concannon offers a fun, grown-up Friday night of stand-up comedy starring Xander Beltran and special guests, held in the intimate Estate Room lounge at Concannon Vineyard in Livermore. This recurring late-night series takes place on the last Friday of the month through August, starting May 29, 2026, at 7:30 PM (doors open at 6:00 PM). The event features top professional comics, a relaxed atmosphere, local food trucks, and award-winning wines and craft beer available for purchase. Tickets are expected to sell out due to the lounge setting, and Wine Club 1883 members receive $5 off their purchase.
Are you planning an event this spring or summer? Feature it so nearby readers see it all across Patch — including in roundups like this!
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