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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Dine & Discover Downtown San Mateo NOW EXTENDED THROUGH OCT 25!
Downtown San MateoExplore Downtown, try new cuisines, win prizes! Now extended through October 25th, 2026! Dine & Discover Downtown San Mateo is a simple way to explore the district’s dining scene and support local businesses. As you visit different restaurants, check in to earn points and prizes. Whether you are local or a visitor, it’s fun way […]
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Italian American Social Club Country Nights
Peninsula Italian American Social Club 100 North B Street, San Mateo, CA, United StatesCountry nights are here! The next Italian American Social Club Country Nights are officially on the calendar! Join us Friday, September 25 and Friday, October 16 for country music by DJ Shivers and beginner-friendly line dance lessons with Line Dancing Lisa. Please make sure to book your tickets on our website in order to secure your spot.
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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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New Class at Baking Arts! Cinnamon Rolls Baking Class
Baking Arts 18 E 3rd Ave, San Mateo, CA, United StatesMaster the art of baking soft, cloud-like cinnamon rolls in this hands-on 120-minute class led by instructor Laura Tyson! Participants will learn how to mix and knead a rich enriched dough, roll and fill it with a cinnamon-sugar swirl, and shape perfect spirals while discovering essential techniques for dough hydration and proper proofing. Each attendee […]
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Karaoke at McGovern’s
McGoverns 215 E 4th Ave, San Mateo, CA, United StatesJoin us for karaoke every Thursday and Sunday at 9:30 PM with $6 well drinks and $7 drafts.
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Bar Bingo Tuesdays at Blue Moon Bar
Blue Moon Bar 215 S B Street, San Mateo, CA, United StatesPlay free Bar Bingo hosted by SF Trivia every Tuesday at Blue Moon Bar in Downtown San Mateo!
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Trivia Night at McGovern’s
McGoverns 215 E 4th Ave, San Mateo, CA, United StatesJoin us for Trivia Night hosted by "Questionable Behavior with Misha" with prizes!
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Weekly Group Guided Meditation (at Tree of Life)
Tree of Life Healing Center for the Soul 316 S Eldorado Street, Suite 100, San Mateo, CA, United StatesBring the nervous system back to a sense of calm with a 30-minute in-person guided meditation led by Tiffany Allen at Tree of Life.