On the Peninsula and into the South Bay, temperatures are rising and people are turning out for fun events and festivals. This May, there’s a lot to celebrate, with AAPI Heritage Month and Cinco de Mayo at the top of mind. Community-driven gatherings take center stage as the South Bay welcomes culture, the planet, art and more.
We’ve done the deep research for you on the best things to do in the South Bay including museums, cultural events, food tours, athletic events, hikes and more. Speaking of food, we also have an extensive list of our best restaurants in the South Bay, and if you’re planning a weekend, the best places to stay.
Featured Photo: Hillsborough Memorial Day Parade
April 4–May 17
Admission is free to this exhibition of contemporary pieces by Latinx artists, on display in downtown San Jose. El Movimiento de Arte y Cultura Latino Americana (MACLA) showcases 30+ California-based Latinx contemporary artists in this annual event, which finishes off with a live auction. Support Latinx artists and MACLA’s missions and continued art preservation by attending.Â
May 3 & 4
Put together by the community group Opening Doors 2020, this festival invites everybody to come dance salsa in Downtown San Jose. Look forward to live music, costumed dancers, a classic car show and loads of food and artisan vendors throughout the day for Cinco de Mayo. Hungry attendees can even compete in a burrito eating contest — a 5-pound burrito eating contest. Proceeds benefit Opening Doors 2020’s mobile meals programs which serve low-income seniors, families and people facing homelessness.
May 10
In the beautiful oceanside city of Half Moon Bay, a weekend of libations and improvisations awaits you. This relatively new music festival takes place on historic Main Street, which musicians and wine vendors will line with tents and plenty of tunes. The main stage will host prominent musicians like Tiffany Austin and Larry Vuckovich with their respective quintets, plus vocalist Jamie Davis, all in one afternoon. And for the other titular component of this festival: you can look forward to wines from nearly 50 vintners.Â
May 17
San Jose’s History Park lights up with a joyous celebration of the South Bay’s diverse Asian American, Native Hawaiian and Pacific Islander communities. Cuisine, performance and discussions are all part of the festivities, with an educational panel by the Japanese American Museum, open exhibits at the Chinese American Historical Museum and Viet Museum and even more activities all filling out the schedule for this free event.
May 24–25
Mushroom art. Mushroom dishes. Mushroom beer?! Learn about, buy and eat all things mushroom at the Morgan Hill Mushroom Festival. Not just a two-day festival for all things mycological, this event also boasts multiple music stages, hours of live entertainment and plenty of shopping on the street. With all these activities, it’s no wonder that the festival is 45 years strong.
May 26
The city of Hillsborough on the Peninsula holds a festive Memorial Day parade every year with marching bands, mounted patrols and community groups all making their way through the city. Be sure to stick around for the music festival slash carnival that follows the parade.Â
Event Venues
Looking to see what’s happening right now in the South Bay? Our comprehensive list of venues below will help you find what you need to know what’s going on.
Looking for more things to do in the area?
Visit our What to Do in Northern California page!
