Things to Do in the San Francisco Bay Area
May 2026
Curated by Thomas Henthorne
The 2026 Bay to Breakers is May 17 in San Francisco
May is one of the most vibrant months of the year in the San Francisco Bay Area, bringing a lively mix of road-race spectacle, neighborhood traditions, cultural festivals, food-and-wine weekends, and creative gatherings across the region. This month’s guide highlights standout events from Bay to Breakers and Carnaval San Francisco to the Marin Irish Festival, Bay Area Book Festival, FanimeCon, and several Wine Country favorites.
While my work is centered in the towns and neighborhoods of Marin County, one of the great pleasures of living here is the easy access to the broader Bay Area. A May weekend might include a festival in San Francisco, a literary event in Berkeley, a makers market in San Jose, a food-and-wine experience in Napa or Sonoma, or a gorgeous Marin hike on one of my favorite local trails. If you are looking to add some time outdoors to your month, my guide to the Top 10 Hikes in Marin County is a great place to start.
If you are looking for fresh ideas for a spring outing, day trip, or weekend built around one memorable event, here are some of the standout things to do around the Bay Area this May.
What’s Happening Around the Bay May 2026
Bay Area Book Festival
May 30-31 Downtown Berkeley becomes a gathering place for authors, readers, activists, and literary voices during one of the Bay Area’s signature cultural festivals. |
Oakland Greek Festival
May 15-17 A long-standing Oakland tradition celebrating Greek food, music, dancing, specialty goods, and the warmth of Hellenic hospitality in the Oakland Hills. |
Marin Irish Festival
May 16-17 Lagoon Park at the Marin County Fairgrounds hosts a lively weekend of Irish music, dance, food, craft vendors, and lakeside celebration. |
A Day on the Green
May 25 Mill Valley’s Memorial Day community concert brings live music, food trucks, activities, and a festive outdoor atmosphere to the Mill Valley Community Center. |
Bay to Breakers
May 17 San Francisco’s legendary race-slash-street-party returns with costumes, crowds, and a 12K route from the Embarcadero to Ocean Beach. |
Carnaval San Francisco
May 23-24 Carnaval returns to the Mission District for Memorial Day weekend with music, dance, food, community, and the 2026 theme “La Copa del Pueblo.” |
Palo Alto May Fete Parade & Fair
May 2 A beloved Peninsula tradition, the May Fete Parade travels along University Avenue before continuing with a community fair at Heritage Park. |
FanimeCon
May 22-25 San Jose welcomes fans, artists, cosplayers, panels, and special guests for one of Northern California’s largest anime and pop-culture conventions. |
SJMADE Fest
May 30-31 History Park hosts SJMADE Fest, a free two-day marketplace featuring makers, artists, designers, food vendors, and creative small businesses. |
South Bay AANHPI Festival
May 16 History Park celebrates Asian American, Native Hawaiian, and Pacific Islander Heritage Month with performances, cuisine, crafts, and community booths. |
Garagiste Festival: Northern Exposure
May 2 Sonoma welcomes small-production winemakers from across Northern California for a rare tasting event focused on hard-to-find wines and artisan producers. |
Healdsburg Wine & Food Experience
May 14-17 This Sonoma County weekend celebrates farmers, growers, winemakers, chefs, and the food-and-wine culture that makes Healdsburg a Wine Country destination. |
Yountville Art, Sip & Stroll
May 16 Yountville’s annual art-and-wine event pairs local art, wine tasting, live music, and a walkable Napa Valley setting centered around town. |
BottleRock Napa Valley
May 22-24 BottleRock returns to Napa Valley Expo for a Memorial Day weekend of music, culinary performances, wine, food, and one of Wine Country’s biggest festivals. |
Considering Moving to Marin?
I hope this guide helps you make the most of May around the Bay. If you are exploring Marin more deeply this spring, you may also enjoy my San Rafael lifestyle guide, my San Anselmo guide, or my new Terra Linda neighborhood page. Together, they offer a closer look at some of Marin’s most appealing communities, from vibrant downtown living to sunny, residential neighborhoods with easy access to open space.
If making a move to or within Marin County is on your horizon, please reach out at 415-847-5584. I am always happy to help you navigate both the market and the lifestyle.
About the Author
Thomas Henthorne is a consistently top-ranked Marin County real estate agent with Golden Gate Sotheby’s International Realty, known for thoughtful guidance, strong negotiation, and polished marketing. He is the publisher of a widely read Marin real estate blog covering local market insights, neighborhood spotlights, and the lifestyle that makes Marin such an exceptional place to live. Thomas also brings a design and branding background to every listing and client strategy, with an emphasis on presentation, positioning, and results.
You can learn more about Thomas here.
Call or text Thomas at 415-847-5584 to discuss your real estate goals.
Let’s Tell the Next Success Story.™
Click Here to Contact Thomas
Please call / text Thomas at 415-847-5584 or fill out this contact form and he will be in touch right away.
Leave a Comment
What do you think?Please leave your comment below!