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
Events
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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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Karaoke (at Blue Moon Bar)
Blue Moon Bar 215 S B Street, San Mateo, CA, United StatesFrom Blue Moon Bar: Join us every Wednesday and Friday at 9:30 PM with your host @xfallingstarx. Sing your heart out in the heart of Downtown San Mateo.
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HEAD WEST Marketplace
B Street between 1st and 3rd AvesVisit Downtown San Mateo’s B Street for HEAD WEST Marketplace on the third Saturday of every month in 2026! Browse unique gifts or find a treat for yourself from local Makers, Merchants, Crafters, Designers, and Artists. While you’re here, explore Downtown’s retail offerings, and enjoy delicious food from our local spots—there’s something for everyone! More […]
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Stand-Up Comedy (at Sky Lounge)
Sky Lounge 76 E 3rd Ave, San Mateo, CA, United StatesThe Bay Area's funniest comedians walk into a lounge... join us for a night of free stand-up comedy at Sky Lounge in San Mateo! Expect fresh jokes, amazing drinks, and zero cover charge. We're bringing you comics who have performed at cobb's Comedy Club, San Francisco Punchline, and San Jose Improv. Doors open at 7:00 […]
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National Library Week: San Mateo Celebrates (at the San Mateo Main Library)
San Mateo Public Library (Main) 55 West 3rd Avenue, San Mateo, CA, United StatesJoin the San Mateo Public Library Foundation for a full week of community, music, science, and story! Highlights include a cooking demo with Martin Yan, a family concert with José-Luis Orozco, storytime and photos with Elephant & Piggie, a biotech talk with Dr. Lisa McGinnis, live Brazilian choro with Grupo Falso Baiano, and a film […]
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Kevin Blake, Magician Extraordinaire (at Peninsula Italian American Social Club)
Peninsula Italian American Social Club 100 North B Street, San Mateo, CA, United StatesFrom the Italian American Women’s Guild: KEVIN BLAKE MAGICIAN EXTRAORDINAIRE As seen on America’s Got Talent, Penn & Teller: Fool Us, Thrillist and in his show The Illusionist at the Palace Theater, Kevin Blake is a San Francisco-based magician, mentalist and illusionist. His show is a mind-bending experience of sleight of hand and mind that […]
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Cinemark Secret Movie Series
Surprise your eyes with Cinemark's Secret Movie Series! Every month, we feature a new, soon-to-be-released film from Hollywood before it comes out. And not only do you get to see the movie early before it's officially out, but you get to see it for only $5! The catch is: the title is totally secret until […]
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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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Karaoke (at Blue Moon Bar)
Blue Moon Bar 215 S B Street, San Mateo, CA, United StatesFrom Blue Moon Bar: Join us every Wednesday and Friday at 9:30 PM with your host @xfallingstarx. Sing your heart out in the heart of Downtown San Mateo.