explore
color and character at every turn
Our history can be seen in the unmistakable architecture that has defined Downtown San Mateo since the 1890s. As you explore on foot, the modern character of Downtown reveals itself in more unexpected places – through vibrant art that comes alive on street poles, in window fronts, and across green spaces.
Take a walking tour of Downtown to discover the latest installations that represent our diverse community.
Downtown Photo Gallery
history
San Mateo was first inhabited by the Ohlone Indians as far back as four thousand years ago. Spanish explorers came to the area in 1776, followed by missionaries who established an outpost at San Mateo in 1793. The abandoned mission later became a stagecoach stop, but it was the arrival of the railroad in 1863 that truly established Downtown San Mateo as a vital commercial center.
Downtown saw major growth after San Mateo incorporated as a town in 1894, and many historic buildings dating from the 1890s to the 1930s can still be seen. You can take an easy Walking Tour to learn more about the history and architecture of the downtown district.
join us at an upcoming event
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Golden Oldies Music Bingo (at Chill Spot Rendezvous)
Chill Spot Rendezvous 271 Baldwin Ave., San Mateo, CA, United StatesFrom Chill Spot Rendezvous: 2nd & 4th Tuesdays of the month 2-4pm Golden Oldies Senior Discount Day Last Thursday of the month 5:30-7:30pm Variety Song List for Everyone!
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Life Coach Workshops (at Chill Spot Rendezvous)
Chill Spot Rendezvous 271 Baldwin Ave., San Mateo, CA, United StatesClarity, Confidence, and Creativity WORKSHOP SERIES by Coach Ranger Enriching workshops led by Coach Ranger from within Range Coaching to help you start 2026 with clarity and confidence. Start 2026 with clarity, confidence, and creativity—three powerful Tuesday evening workshops in San Mateo to help you grow personally and professionally. Only $10/session, all proceeds support local […]
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Sunset Trivia (at O’Neills)
O'Neill's Irish Pub 34 South B Street, San Mateo, CA, United StatesUnearth your team's potential at O'Neills Irish Pub in San Mateo! This vibrant spot, perfect for continuing your evening, hosts exhilarating trivia every Wednesday at 7:15 PM. Gather your sharpest minds, join the craic, and put your knowledge to the ultimate test. Will you be the lucky team to claim victory? This is a recurring […]
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Latin Night Dance Party (at Motion Arts Center)
Motion Arts Center 217 South Claremont Street, San Mateo, CA, United StatesFrom Motion Arts Center: Join us for our weekly Latin Night Dance Party filled with Salsa, Bachata, and Cumbia music! Come, bring your friends and get ready for an unforgettable night of dancing and fun on the dance floor. We will provide snacks and light drinks. The dance studio has air conditioning, a beautiful hardwood […]
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Salsa 4 Week Workshop Series with Chris and Jewell (at Motion Arts Center)
Motion Arts Center 217 South Claremont Street, San Mateo, CA, United StatesCome join our fun Salsa 4-Week Workshop Series, taught by the wonderful instructors Chris & Jewell! This progressive series is designed to give you a strong foundation in salsa while helping you feel more confident, musical, and connected to your partner on the dance floor. Over four consecutive weeks, you’ll dive deep into both footwork […]
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Downtown San Mateo Walking Tour (with San Mateo Forward)
From San Mateo Forward: Join San Mateo Forward for a walking tour of downtown San Mateo! We’ll answer questions like: What’s currently happening inside Draeger’s, now that the store is gone? What’s planned for downtown San Mateo? Which parking structure is the most structurally sound, and why? We’re a group of San Mateo residents who […]
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Balourdet Quartet (at the San Mateo Public Library)
San Mateo Public Library (Main) 55 West 3rd Avenue, San Mateo, CA, United StatesMusic at Kohl Mansion and the San Mateo Public Library present a Musical Conversation with the Balourdet Quartet, featuring music by Béla Bartók, Amy Beach, Eleanor Alberga, and Johannes Brahms. Established in 2018 and winners of multiple international awards, the Quartet is Angela Bae & Justin DeFilippis, violins; Benjamin Zannoni, viola; Russell Houston, cello. The […]
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Life Coach Workshops (at Chill Spot Rendezvous)
Chill Spot Rendezvous 271 Baldwin Ave., San Mateo, CA, United StatesClarity, Confidence, and Creativity WORKSHOP SERIES by Coach Ranger Enriching workshops led by Coach Ranger from within Range Coaching to help you start 2026 with clarity and confidence. Start 2026 with clarity, confidence, and creativity—three powerful Tuesday evening workshops in San Mateo to help you grow personally and professionally. Only $10/session, all proceeds support local […]
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Sunset Trivia (at O’Neills)
O'Neill's Irish Pub 34 South B Street, San Mateo, CA, United StatesUnearth your team's potential at O'Neills Irish Pub in San Mateo! This vibrant spot, perfect for continuing your evening, hosts exhilarating trivia every Wednesday at 7:15 PM. Gather your sharpest minds, join the craic, and put your knowledge to the ultimate test. Will you be the lucky team to claim victory? This is a recurring […]