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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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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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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Cinemark Summer Movie Clubhouse
Enjoy family-friendly movies for just $1.75 per ticket, plus special $1 off concession deals.
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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.
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Downtown San Mateo Farmers’ Market
Draeger's 222 E 4th Ave, San Mateo, CA, United StatesCome support the Downtown San Mateo Farmers’ Market! West Coast Farmer’s Market brings a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your afternoon stroll. Support local farmers and this weekly Downtown Farmer’s Market—it all starts with you. The market is located in the parking lot of the […]
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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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Karaoke World Championships USA Qualifier (at McGovern’s)
McGoverns 215 E 4th Ave, San Mateo, CA, United StatesMcGovern's Bar hosts the Solo 21+ Qualifier Round for the 2026 Karaoke World Championships.
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Soccer Social Pop Up
South B Street South B Street (Between Baldwin Ave. & 2nd Ave.), San Mateo, CA, United StatesFrom the City of San Mateo: Learn more about Soccer Celebrations and participating businesses HERE All 2026 San Mateo Soccer-related events: Event Date Time Location Soccer Social Pop-Up Friday, June 12, 2026 5:00 PM - 8:00 PM B Street Pedestrian Mall, Downtown San Mateo Fan Zone Watch Party Thursday, June 25, 2026 6:45 PM - […]