Bay Area Events | May 2024


Our sunny California weather is back, and along with it arrives plenty of opportunities to enjoy the outdoors of our gorgeous Bay Area! Head to the ballpark by the water to watch our very own San Francisco Giants in action at Oracle Park during one of 13 home games this month. Check out the Bay Area’s incredible live music scene at one of many concerts and festivals below. Plan to celebrate moms on Mother’s Day (May 12!) with a sunny brunch, sunset cruise, or garden stroll.

This month’s options are pretty much endless, so make the most of your May!


Cinco de Mayo Salsa Fest | Downtown San Jose | May 4

Take part in the city’s huge annual Cinco de Mayo festival featuring live music and salsa dancing, delicious food and drinks, and a beautiful array of local arts and crafts. For tickets and info, click here.

Santa Clara Valley Wine Auction | San Martin | May 4

Don your favorite Derby hat and discover the amazing wine and culinary delights of the Santa Clara Valley at this year’s “Kentucky Derby Style” Wine Auction at beautiful Clos La Chance Winery. Vineyard views and live music set the stage for an incredible evening. For tickets and more info, click here.

Home Tour | Willow Glen | May 4-5

Enjoy an afternoon touring five featured homes and a garden boutique in one of San Jose’s most treasured neighborhoods. Docents will be on site to answer questions about the history, architecture, and design of these enchanting homes.  For tickets, click here.

***** HAPPY MOTHER’S DAY! May 12 ******

77th Kiwanis Pet Parade | Downtown Los Altos | May 18

Hundreds of kids and their pets – dogs, cats, birds, chickens, turtles and even worms – parade through Downtown Los Altos during this beloved community tradition. Click here for more information or to register your pet!

KRTY Songwriter Series At Clos La Chance | San Martin | May 23-24

KRTY radio and Clos La Chance partner together to bring a series of special country music events and artists to the winery. Once a month from May – October, you can enjoy a beautiful evening under the stars listening to some of your favorite songs performed by the songwriters themselves. For more information and tickets, visit

Boogie Music Festival | Downtown Campbell | May 18-19

Get your boogie on! Named one of the South Bay’s best music festivals for multiple years, this two-day event in historic Downtown Campbell features four entertainment stages, continuous live music, food, beer and wine, arts and crafts, and fun for the whole family. Admission is free with varying prices for food, drink, and other festival activities. Visit

Zappos Bay To Breakers Race | San Francisco | May 19

This legendary foot race is a “12K-long party” and a true San Francisco original. More than 50,000 runners race through the city in colorful costumes from the Bay on the eastern side, all the way to the Breakers on the western coast of the city. For more information, click here.

BottleRock | Napa Valley | May 24-26

This large-scale music festival features three full days of star-studded lineups, great food, and wine, combining a vibrant atmosphere with gorgeous natural surroundings. Visit for more info, tickets, and lodging packages.

Memorial Day Celebration | San Francisco | May 27

Head over to the Presidio for this year’s Memorial Day Celebration honoring our nation’s veterans at the National Cemetery, one of the largest celebrations on the West Coast. A band concert kicks off the celebration at 10:30AM. Learn more here.

Wine & Jazz Festival | Half Moon Bay | May 31—June 1

Enjoy a perfect performance of wine and jazz at the coast in beautiful Half Moon Bay. Sample from 50 renowned California wineries and enjoy nationally known artists, plus food trucks and a beer and cider garden, all on historic Main Street. Visit for more info.