Self-Guided Walking Tour
The town began right here, at B Street and Third Avenue. Take a slow walk past the century-old storefronts and here's what you're actually looking at.
San Mateo started as a Catholic mission outpost in the 1790s and a stage stop between San Francisco and San Jose. The railroad made it a town: by the 1880s, brick buildings lined the square around the station, and for decades South B Street was where everyone shopped, the pharmacies, meat markets, cigar stores, hardware and lumber.
When East Third Avenue filled in through the 1920s and 1930s, San Mateo boomed as a San Francisco suburb, and the downtown took on the Spanish Colonial and Art Deco look it still wears. When the malls arrived in the 1950s, the big stores drifted south to Hillsdale, and that quiet exodus is exactly what left downtown's 1930s character intact. Here are the stops worth slowing down for.
Building histories drawn from the City of San Mateo Planning Division's Downtown Historic Building Self-Guided Walking Tour. Most of these buildings still stand, look up above the storefronts. Each stop also shows what’s there today, so you know you’re in the right spot (checked October 2026; storefronts change, so look for the address numbers too). Tap “History of this address” on a stop to see the businesses that came before, with sources.
Our pick of 19 highlights from the City’s longer historic tour, with what’s in each building today and the stories behind the addresses.
Simplified map from each stop’s location. Numbers match the stops below.
The city's original main street.
An early survivor in the Mission Revival style. Robert Wisnom, a giant of early San Mateo commerce and construction, ran a lumber yard behind this building starting in the 1880s. The Wisnom name is on storefronts all over downtown.
Find it → Next: 2. Odd Fellows Hall ↓One of the oldest structures left on B Street, built for the Odd Fellows, the oldest fraternal organization in San Mateo. It also housed the San Mateo Market and the Mountain View Fruit Company. Note the richly detailed brick upper bays.
Find it → Next: 3. Noah's Cafeteria (site) ↓In the 1920s this address was Noah's Cafeteria, run by one of the first known Black businessmen in San Mateo. Well known across the area with a growing clientele, Noah later moved his restaurant up to Third Avenue.
Find it → Next: 4. The old bank building ↓An elegant Greek Revival building that cost $50,000, designed by architect W.H. Weeks and built by Samuel Wisnom, one of Robert's sons. Its original occupant was the National Bank of San Mateo, and it’s on the National Register of Historic Places. Look for the paired fluted pilasters.
Find it → Next: 5. The House of Merkel ↓Considered by many the most significant historic building in San Mateo. German immigrants Carl and Cuna Merkel opened a cigar store on this corner in 1918, then built this Art Deco landmark and filled it with a soda fountain, confectionary, liquor store, billiard parlor, and horse betting. It was a gathering place for over fifty years. Look up at the octagonal corner bays and terra cotta tiling.
Find it → Next: 6. Old City Hall ↓This was San Mateo City Hall for nearly fifty years. The old judge's chamber still occupies the second floor, and a prison cell and a rifle range are tucked in the basement. The B Street frontage keeps its prominent ground-floor arches.
Find it → Next: 7. The Woolworth building ↓A stylish Art Deco storefront that was home to the F.W. Woolworth five-and-dime in the late 1930s. Note the stepped vertical elements and the patterns sculpted into the stucco.
Find it → Next: 8. The market building ↓Over the years this Spanish-mission-influenced building held the Tasty Cake Shop, a Piggly Wiggly, and a Safeway. One of its three storefronts still keeps its original transom window under the sloping clay-tile roof.
Find it → Next: 9. National Bank of San Mateo ↓A reinforced-concrete Mission Revival building that housed the National Bank of San Mateo, San Mateo Hardware, and Pope's Drug Store in its first thirty years. The same bank’s 1925 building is up the street at 164 S B St (stop 4).
Find it → Next: 10. The Medical Arts Building ↓The 1920s and 1930s suburban boom.
A handsome modernistic block with Art Deco ornament, one section four stories, one three. Chevrons decorate the spandrels between the piers, and the splayed main entrance keeps its original ornamental tile in stylized floral and geometric patterns.
Find it → Next: 11. Schneider's ↓A simple modern building with Art Deco details at Third and Ellsworth. Its early tenant was the Greenline Drug Company; JCPenney moved in during the mid-1940s; and for decades after the 1950s it was home to Schneider's, a locally owned clothier. Schneider's has since closed, but the building keeps its clean Art Deco lines.
Find it → Next: 12. The Avansino Building ↓San Francisco architects Fabre and Hildebrand designed this concrete-and-terra-cotta professional building for $28,000. Known for years simply as the Avansino Building, it has housed local businesses and offices since 1937.
Find it → Next: 13. J.J. Newberry ↓The five-and-dime J.J. Newberry & Company moved in as the first tenant in 1935 and stayed until 1957, when it followed the shoppers south to the brand-new Hillsdale Mall, a small moment that captured the whole downtown-to-mall shift.
Find it → Next: 14. The old San Mateo Theatre ↓Once a downtown movie theatre, later converted to offices. Its marquee and surface decoration were stripped away and a new front pushed out for ground-level shops, but the original upper portion is still visible above.
Find it → Next: 15. Levy Brothers ↓An excellent Tudor-style building, decorative half-timbering, an elaborate chimney, scalloped bargeboards, a rare bit of storybook architecture downtown. For years this was the Levy Brothers store, a San Mateo retail institution.
Find it → Next: 16. The Benjamin Franklin Hotel ↓Eight stories, built for $250,000 as a resort for vacationing San Franciscans, designed by architect W.H. Weeks. The building still stands and still anchors the block, even as new businesses fill it.
Find it → Next: 17. The Raybould & Johnson building ↓An idiosyncratic two-part block with a ribbon of casement windows, a semi-elliptical surround, and a whimsical red-and-white checkerwork cornice. It was built for Raybould and Johnson, realtors who subdivided many of San Mateo's grand old estates.
Find it → End of the main route. Two bonus stops are a block from stop 4 ↓Worth the short detour.
Built as the Wisnom Hotel and renamed the Hotel St. Matthew in 1920, this handsome brick building is the only remaining downtown hotel of its era, with four octagonal window bays projecting above the ground floor. It's on the National Register of Historic Places.
Find it → Next: 19. The old fire station ↓This Spanish Colonial Revival fire station is all that remains of the 1940-era City Hall complex. Look for the hipped tile roof over all three sections and the lunettes arching over each door.
Find it → Back to the route map ↑