Spring is in full swing, and May is bringing a fresh wave of excitement to the Peninsula and South Bay. From the return of beloved community traditions to innovative new flavors and unique outdoor performances, there is plenty to explore this month.
Whether you’re looking to enjoy a scenic bike ride down El Camino Real or grab a refreshing new boba tea, here is what’s happening in our backyard this May.
Redwood City & San Carlos
Hometown Days
📍 900 Chestnut St, San Carlos
A local favorite is back! Burton Park hosts San Carlos Hometown Days from May 15–17. This weekend-long celebration is the heart of "The City of Good Living," featuring a parade, live music, local food vendors, carnival rides, and activities for the whole family. This year’s festivities will also include a Rotary Fun Run and Pancake Breakfast on Sunday morning, plus multiple live entertainment stages throughout the weekend. It’s the perfect way to kick off the pre-summer season with your neighbors. Visit the City of San Carlo website to learn more.
Woodside & Portola Valley
In a Landscape at Filoli
📍 86 Cañada Rd, Woodside
Experience the magic of Filoli like never before. On May 18, "In a Landscape" brings a classical music experience to the historic estate’s lush gardens. Imagine a grand piano set against the backdrop of blooming spring flowers while you wander the grounds with wireless headphones. Guests can also explore Filoli’s Formal Garden and surrounding natural lands during the performance, making it a truly immersive evening blending music, architecture, and nature. It’s a stunning intersection of nature and art. Visit Filoli.org to learn more.
Palo Alto & Los Altos
Wow Tea Drink
📍 2515 El Camino Real Suite 110, Palo Alto
Palo Alto’s boba scene just got a major upgrade. Wow Tea Drink is now open, serving up vibrant, high-quality tea concoctions brewed with premium ingredients and teapresso-style machines. In addition to fruit-infused refreshments and creamy classics, the shop has quickly gained attention for its tea gelato flavors and signature rice mochi milk teas. Its bright, modern interior and convenient El Camino location make it an easy stop for a mid-afternoon pick-me-up on the Peninsula. Visit their website to learn more.
Sunnyvale & Mountain View
Avakai & Co
📍 1191 E Arques Ave, Sunnyvale
Sunnyvale welcomes Avakai & Co, a fresh addition to the local dining landscape. Known for their curated menu that blends modern techniques with comforting flavors, it’s a must-visit for foodies looking for a new brunch or lunch destination in the heart of Silicon Valley. The café-style space emphasizes seasonal ingredients and a relaxed atmosphere, making it equally suited for casual weekday lunches or weekend meetups with friends. Visit their website to learn more.
Santa Clara & Cupertino
XiangBobo Hunan Cuisine
📍 10350 S De Anza Blvd, Cupertino
Spice lovers, rejoice! XiangBobo Hunan Cuisine has arrived in Cupertino. Bringing the bold, fiery, and authentic flavors of Hunan province to the South Bay, this new opening is already garnering attention for its signature stir-fries, chili-forward dishes, and traditional spices. Diners can expect classic Hunan specialties known for their smoky heat and layered flavors, all served in a modern and family-friendly dining space. Visit XiangBobo website to learn more.
San Jose
Global Spice Kitchens
📍 949 Ruff Dr, San Jose
San Jose continues to be a melting pot of culinary innovation with the opening of Global Spice Kitchens. This concept focuses on bold international flavors and high-quality ingredients, offering a diverse menu that celebrates spices from around the world. The venue also highlights globally inspired comfort food and rotating regional specialties, giving visitors something new to discover with every visit. Explore Global Spice Kitchens.
Featured Event: 2026 El Camino Real Ride
El Camino Real Ride
📍 Peninsula Corridor from Santa Clara to Menlo Park
🗓 Saturday, May 30, 2026
Dust off your bikes for the El Camino Real Ride! On May 30th, join fellow cyclists for a scenic journey from Santa Clara all the way to Menlo Park. This community-focused ride encourages sustainable transportation and active living while showcasing some of the Peninsula’s most iconic neighborhoods and historic corridors. Riders of varying experience levels are welcome, making it a fun and accessible way to experience the Bay Area from a different perspective. Event details and registration.
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