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.


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
Highland Park Single Malt Scotch Whisky Tasting (at Fogbird)
Fogbird 144 S B St, San Mateo, CA, United StatesFor more information, visit https://www.exploretock.com/fogbird/event/549201/highland-park-single-malt-scotch-whisky-tasting Event includes: - 3/4 oz. taste of 4 different Highland Park Single Malt Scotch Whiskys: 12 Year 15 Year 18 Year 21 Year PLUS: - […]
Beaute & Bosses (at Y Salon)
Y Salon Spa 241 S San Mateo Dr,, San Mateo, CA, United StatesA networking & beauty experience! Hairstyling - mini makeovers - braids - wellness - bites & sips - local vendors - IV vitamin infusion
Karaoke World Championships (at McGoverns)
McGoverns 215 E 4th Ave, San Mateo, CA, United StatesFrom the Karaoke World Championship: Are you the next Karaoke World Champion for 2025?... We invite you to try out for the Karaoke World Championships Global Music Contest where every […]
First Friday Dinner Dance (at the Peninsula Italian American Social Club)
Peninsula Italian American Social Club 100 North B Street, San Mateo, CA, United StatesFirst Friday of each month. Please visit peninsulaitalianclub.org/club-events for more details.
Cinema & Chill (at Chill Spot Rendezvous)
Chill Spot Rendezvous 271 Baldwin Ave., San Mateo, CA, United StatesFrom Chill Spot Rendezvous: CINEMA & CHILL EVERY SATURDAY 12pm-4pm Hangout and enjoy family friendly movies- free every Saturday. Bring yourself and/or your family for movies through the day. Join […]
DSMA Board Meeting (Open to the Public)
The Downtown San Mateo Association Board and staff, representatives from the City of San Mateo, DSMA members, and other community members gather each month to discuss DSMA business. If you […]
Death’s Head Hawkmoth Pinning Class (at Golden Moon Gallery)
Golden Moon Gallery 28 East 3rd Avenue Ste. 101, San Mateo, CA, United StatesFrom Silver Moon Curiosities: Join us on Friday the 13th! Learn to pin a Death's Head Hawkmoth at @goldenmoongallery in San Mateo. This will be a beginner-friendly, hands-on class appropriate […]
HEAD WEST Marketplace
South B Street South B Street (Between Baldwin Ave. & 2nd Ave.), San Mateo, CA, United StatesVisit Downtown San Mateo's B Street for HEAD WEST Marketplace on the third Sunday of every month in 2025! Browse unique gifts or find a treat for yourself from 50 […]
First Friday Dinner Dance (at the Peninsula Italian American Social Club)
Peninsula Italian American Social Club 100 North B Street, San Mateo, CA, United StatesFirst Friday of each month. Please visit peninsulaitalianclub.org/club-events for more details.