🌞 May 2025 Events in the South Bay & Peninsula
May is here, and with it comes sunshine, community vibes, and an amazing lineup of local events! Whether you're in San Jose, Los Gatos, Sunnyvale, Palo Alto, or Peninsula cities like San Mateo, Redwood City, and Burlingame — there’s something happening near you.
Here’s your curated guide to the best events this May!
🌼 Spring Festivals & Family Fun
Cupertino Cherry Blossom Festival
📍 Memorial Park, Cupertino | 📅 May 4–5, 2025
Celebrate Cupertino’s sister-city relationship with Toyokawa, Japan! Enjoy Japanese cultural performances, art, crafts, and food booths. A great day out for families!
Kidchella: Family Music Festival
đź“Ť Magical Bridge Playground, Palo Alto | đź“… May 11, 2025
Live music, interactive play zones, crafts, and kid-friendly food trucks make this event a must for little ones and their grown-ups.
🎶 Live Music & Entertainment
Music in the Park – San Jose
📍 Plaza de César Chávez, San Jose | 📅 May 23, 2025
This free concert series kicks off in May with live bands, local food vendors, and a high-energy crowd. Bring your blanket and dancing shoes!
Los Gatos Music in the Park Preview Night
đź“Ť Civic Center Lawn, Los Gatos | đź“… May 26, 2025
Enjoy a sneak peek of the summer lineup with live music and food trucks in a relaxed, family-friendly setting.
🍷 Wine, Beer & Food Events
San Mateo Wine Walk
đź“Ť Downtown San Mateo | đź“… May 18, 2025
Sip, shop, and stroll your way through local shops and restaurants while sampling wine from around the region.
Campbell Beerwalk: Star Wars Theme
đź“Ť Downtown Campbell | đź“… May 4, 2025
Grab your lightsaber and explore downtown while tasting beers from local breweries. Costumes encouraged!
🎠Theater & Performing Arts
South Bay Musical Theatre – Legally Blonde
📍 Saratoga Civic Theater | 📅 May 3–19, 2025
This upbeat musical will have you dancing in your seat. A fun night out whether you're a theater lover or just need a girls’ night!
Broadway by the Bay – Into the Woods
📍 Fox Theatre, Redwood City | 📅 May 10–26, 2025
Catch this stunning production of Sondheim’s fairytale-inspired musical at the historic Fox Theatre.
🛍️ Markets & Community Events
Downtown Campbell Farmers’ Market
đź“Ť Downtown Campbell | đź“… Every Sunday in May
Shop fresh produce, flowers, local honey, and handmade crafts at one of the most beloved markets in the South Bay.
Burlingame ArtzFest
📍 Downtown Burlingame | 📅 May 31 – June 1, 2025
A two-day celebration of art, music, food, and family fun! Shop works from over 150 artists, enjoy live performances, and discover local eats.
đźš´ Outdoor & Fitness Events
Viva CalleSJ
đź“Ť Streets of San Jose | đź“… May 19, 2025
Streets are closed to cars and open for people! Walk, bike, skate, and dance your way through San Jose with live music, food trucks, and pop-up fun zones.
Hike Fremont Older Preserve
đź“Ť Saratoga | đź“… Any Day in May
A local favorite for wildflowers, scenic views, and a good workout. Great way to recharge and connect with nature.
đź’ˇ Final Thoughts
May in the South Bay and Peninsula is buzzing with energy, creativity, and connection. From music festivals and wine walks to family-friendly celebrations and farmers' markets, there’s something for everyone this month.
✨ Thinking of buying or selling a home while enjoying all this spring magic? Let’s connect — I’m here to help you make smart, confident moves in today’s real estate market.
đź“© Reach out anytime for insights, guidance, and local know-how!
