Come Experience the Magic of HEADWEST Marketplace in San Mateo!
Join us every 3rd Sunday of the month in the heart of Downtown San Mateo for a day filled with sunshine, creativity, and conscious community vibes! From handmade goods and sustainable art to crystals, music, and local eats—HEADWEST is more than a market, it’s a movement.
HEADWEST Marketplace | San Mateo
📅 3rd Sunday of Every Month • 11 AM–5 PM
📍 South B Street, Downtown San Mateo (1st Ave to 3rd Ave)
✨ Local Vibes & Community Roots
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Community Focused – Juried and curated in-house by a dedicated “HW Family” of creatives. HEADWEST champions diversity and welcomes BIPOC, AAPI, LGBTQIA+, and differently-abled makers, offering community booth spots for rising artists.
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Eco-Conscious Approach – Proudly a “Clean + Green” market since 2020, reducing plastic waste, banning vinyl signage, and donating 1% of revenue through “1% for the Planet” initiatives.
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Downtown Destination – Set across five bustling blocks filled with 100+ restaurants, boutiques, and local art. The pedestrian-friendly South B Street becomes a vibrant open-air hub every month .
🎤 Good Vibes & Experiences
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Enjoy live music, artisan conversations, healthy bites, and a family-friendly atmosphere—bring your water bottle, pet, and curiosity .
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Vendors receive full event support, including custom social media kits, load-in logistics, and booth coordination—a well-organized experience from start to finish .
Why Visit Us at HEADWEST?
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Crystals + Conscious Creativity – Shop handcrafted gemstone water bottles, crystal jewelry, raw and polished stones, and our delightfully mysterious Gem-Ball Machine.
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Meaningful Connections – Meet like-minded souls, support independent makers, and immerse yourself in San Mateo’s lively downtown scene.
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Sustainable Shopping – Align with eco-conscious practices in a welcoming, vibrant marketplace setting.
🗓️ Plan Your Visit
HEADWEST Marketplace
When: 3rd Sunday each month
Time: 11 AM–5 PM
Where: South B Street, Downtown San Mateo
Cost: Free admission, pet & family friendly, ADA accessible, rain or shine
Stay sneaky on weather and vendor news by subscribing to HEADWEST’s newsletter or following @headwestmarketplace online.
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