May brings many, many opportunities to enjoy our sunny, gorgeous Bay Area outdoors! Explore the Bay Area’s incredible live music scene at one of many concerts and festivals below, and celebrate moms on Mother’s Day on May 11 with a brunch, sunset cruise, or garden stroll. Or, head to the ballpark by the Bay to watch our very own San Francisco Giants in action at Oracle Park at one of 13 homes games this month.
The sun is back—and I’m looking forward to seeing you out there!
Neighborhood Home Tour | Willow Glen | May 3-4
Explore one of San Jose’s most treasured neighborhoods at the 41st 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.
Cinco de Mayo Festival | San Jose | May 4
Enjoy this city’s huge, annual Cinco de Mayo festival! Come to Plaza Cesar de Chavez in Downtown San Jose and celebrate Mexican history with entertainment, delicious food, drinks, and a beautiful array of local arts and crafts. For tickets and info, click here.
Wine & Jazz Festival | Half Moon Bay | May 10
Savor the perfect combination of wine and jazz on the coast in beautiful Half Moon Bay. Sample from 50 renowned California wineries and enjoy nationally renowned 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 11 ******
77th Kiwanis Los Altos Pet Parade | Los Altos | May 17
Hundreds of kids and their pets—dogs, cats, birds, chickens, turtles, and even worms!—parade through Downtown Los Altos in this beloved community tradition. Click here for more information or to register your pet!
Boogie Music Festival | Campbell | May 17 & 18
Get ready to boogie in Downtown Campbell! Named one of South Bay’s Best Music Festivals for multiple years, this two-day event 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, beverages, and other festival activities. Visit DowntownCampbell.com.
Zappos Bay to Breakers Race | San Francisco | May 18
Join the party! 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 to the Breakers on the city’s western coast. For more information, click here.
Song & Wine Series 2025 | San Martin | May 22 & 23
Enjoy a beautiful evening under the stars at Clos La Chance Winery, sipping a glass of wine and listening to some of your favorite country songs performed by the songwriters themselves. Once a month from May through October, this special series brings writers that have multiple hit songs and are experienced performers to the stage in this stunning setting. It is truly one of a kind! For more information and tickets, visit clos.com.
BottleRock | Napa Valley | May 23 – 25
Kick off summer with music, wine, food, and fun in beautiful Napa Valley! This large-scale music festival features three full days of star-studded lineups and gourmet food and wine, bringing a vibrant atmosphere to a gorgeous Wine Country landscape. Visit bottlerocknapavalley.com for more info, tickets, and lodging packages.
Memorial Day Celebration | San Francisco | May 26
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. The events kicks off with a classic band concert tribute at 10:30AM. Learn more here.
