May in the Bay Area is when everything comes alive: longer days, sunshine-filled weekends, and a calendar full of events worth getting out for. From vibrant festivals and live music to coastal escapes and neighborhood traditions, there’s something for everyone to enjoy.
Whether you’re celebrating Mother’s Day, catching a game by the water, or simply soaking in the season, May is the perfect time to roam about. I’ll see you out there!
Home Tour | Willow Glen | May 2-3
Explore one of San Jose’s most treasured neighborhoods at the 42nd Annual Willow Glen Home Tour with an insider’s look at five featured homes, plus a garden boutique for refreshments and more. Learn from on-site docents about the history, architecture, and design of these enchanting homes. For tickets, click here.
Downtown Cinco De Mayo Festival | San Jose | May 3
Enjoy the city’s third annual Cinco de Mayo festival in Cesar Chavez Plaza celebrating Mexican history with live music and dancing, delicious food and drinks, and a beautiful array of local arts and crafts. For tickets and info, click here.
Wine & Jazz Festival | Half Moon Bay | May 9
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 hmbwineandjazzfest.com for more info.
**Happy Mother’s Day! May 10**
79th Kiwanis Pet Parade | Los Altos | May 16
Enjoy this beloved community pet promenade in Downtown Los Altos as hundreds of kids, adults, and their pets—dogs, cats, birds, chickens, turtles, and even worms—parade in colorful costumes. Click here for more information or to register your pet!
Boogie Music Festival | Campbell | May 16 & 17
Get ready to boogie in Downtown Campbell! This award-winning two-day festival features four entertainment stages, continuous live music, food, beer & wine, arts, crafts, and fun for the whole family. Admission is free with varying prices for food, drink, and other festival activities. Visit DowntownCampbell.com.
Bay To Breakers Race | San Francisco | May 17
Join the party! This historic fun run is a “12K-long party” and made for everyone. More than 50,000 runners annually race through the city in colorful costumes from the Bay on the Eastern side, to the Breakers on the western coast of the City. For more information click here.
Memorial Day Celebration | San Francisco | May 25
Honor our nation’s veterans at the Presidio for this year’s Memorial Day Celebration at the National Cemetery, one of the largest celebrations on the West Coast, kicking off with a band concert at 10:30AM. Learn more here.
