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
Painting and Vino (at Fogbird)
Fogbird 144 S B St, San Mateo, CA, United StatesFrom Painting & Vino: Join us for drinks, art and fun at FOGBIRD! Get ready for a creative, fun-filled night of painting and socializing at this beginner “ISLAND DREAM” paint and […]
2025 Central Park Music Series with Pop Fiction (Dance Party)
San Mateo Central Park 50 E 5th Ave, San Mateo, United StatesFrom City of San Mateo Parks & Rec: Concert Dates & Band Line-Up: Thursday, June 26, 2025 - 6-8 p.m. Native Elements (Reggae) Friday, July 4, 2025 - 11:00am - […]
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 […]
Bay Area Fit Fest (at Central Park)
San Mateo Central Park 50 E 5th Ave, San Mateo, United StatesBay Area Fitness Festival 2025 General Admission: Free Sweat Pass: $10 https://www.eventbrite.com/e/bay-area-fit-fest-tickets-1320666672569 This isn't just a fitness event- it's a full-on wellness experience. Get ready to SWEAT with the Bay […]
Farmer’s Market (from West Coast Farmer’s Market Association)
Draeger's 222 E 4th Ave, San Mateo, CA, United StatesHelp support local farmers and a weekly Downtown Farmer’s Market — it all starts with you. 222 4th Ave, in the parking lot of the former Draeger’s Market Sundays 9 […]
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 […]
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!
Painting and Vino (at Fogbird)
Fogbird 144 S B St, San Mateo, CA, United StatesFrom Painting & Vino: Join us for drinks, art and fun at FOGBIRD! Get ready for a creative, fun-filled night of painting and socializing at this beginner “RED BIRDS ON […]
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!