Downtown is where San Mateo began. Laid out alongside the railroad in 1863, the blocks around B Street and Central Park are still the city's beating heart, home to the restaurants, the bars, the farmers' market, and the Caltrain that started it all.
San Mateo began as a Catholic mission outpost in the 1790s and grew slowly as a stage stop halfway between San Francisco and San Jose. What turned it into a town was the railroad. In 1863, under Charles B. Polhemus, a director of the new San Francisco to San Jose line, the first train reached San Mateo, making the run from the city in just thirty-seven minutes. The station came first, buildings rose around Main Street and Railroad Avenue, and by the 1880s brick storefronts lined the square by the tracks. Downtown was born at B Street and Third Avenue, and that is still its heart today.
For decades, South B Street was where San Mateo shopped: pharmacies, meat markets, groceries, cigar stores, hardware and lumber. Much of it went up thanks to the Wisnom family, pioneer builders who ran a lumber yard here from the 1880s and whose name is still on several downtown buildings. The old Wisnom Hotel on Second Avenue, built in 1900 and renamed the Hotel St. Matthew in 1920, is the last downtown hotel of its era still standing. The 1891 Odd Fellows Hall on B Street, home to the city's oldest fraternal order, is one of the oldest buildings left.
As East Third Avenue filled in through the 1920s and 1930s, San Mateo became a booming San Francisco suburb. At one point newspapers claimed 85 percent of locals commuted to the city, and downtown took on the Spanish Colonial and Art Deco look it still wears. The showpiece was the House of Merkel at 201 South B Street, an Art Deco landmark where German immigrants Carl and Cuna Merkel ran a cigar store, soda fountain, confectionary, billiard parlor, and even horse betting, a gathering place for over fifty years. A few blocks over, the eight-story Benjamin Franklin Hotel opened in 1927 as a resort for vacationing San Franciscans.
Downtown has layers most people walk right past. The old City Hall at 215 South B Street served from 1914 to 1961 and still hides a judge's chamber upstairs and a prison cell and rifle range in the basement. In the 1920s, 139 South B Street was Noah's Cafeteria, run by one of the first known Black businessmen in San Mateo. When Hillsdale's mall opened in the 1950s, anchor stores like J.J. Newberry drifted south, and that quiet exodus is part of what preserved downtown's 1930s character. A walk down B Street and Third today still conjures the town San Mateo used to be.
Family-run coffee house with what regulars call the best espresso in the county, warm rotating local art, and sunny sidewalk seating.
Scratch-made Northern-Italian plates and house pastas with an all-Italian wine list; a Michelin Guide listee.
The Peninsula's in-house dry-aging steakhouse, with the meat locker visible at the entry.
All-you-can-eat rodizio with tableside skewered meats carved to order.
Generous rolls and traditional sushi in a casual room with a strong catering side.
Modern-leaning Thai with curries, pad see ew, and customizable spice levels.
Naturally leavened artisan breads and pastries baked fresh daily, visible through the open bakery windows.
Owner-run Italian-style cafe serving espresso plus homemade breakfast and brunch like Sicilian omelette, carbonara, and tiramisu.
French-inspired bakery known for croissants, macarons, scones, and vegan/gluten-free pastries.
Friendly neighborhood coffee shop on South B Street with long daily hours and Turkish-coffee options.
Hong Kong-style bakery with artisan breads, Asian-inspired pastries, custom cakes, and specialty drinks.
Craft cocktails and bar bites in a high-ceilinged room with an original brick wall and a nine-foot bar.
Reservation-only underground cocktail bar with an inventive, whimsical drink list.
Hundreds of wines by the glass and bottle paired with cheese and charcuterie boards, seafood, and cocktails.
Family-run wine and bruschetta spot since 2006 with live jazz on weekends and a real happy hour.
A cozy wine bar and art gallery pouring a curated selection of wines from around the world, with charcuterie and small plates, plus regular comedy and events.
A longtime family-run taqueria from the lineage credited with the original Mission-style burrito, hefty burritos, a full vegan menu, and $3.99 cocktails on Thursday nights.
Comfortable downtown Irish-style pub and local hangout with a global beer and drink mix.
A longtime downtown Irish pub since 1998, steps from the Caltrain station, with a full bar, sports on the screens, and live music, trivia, and karaoke through the week.
Modern Filipino cooking in downtown San Mateo, with elevated takes on kare kare, sinigang, pancit, and lumpia.
A quesabirria specialist near downtown known for birria tacos with consome for dipping. Closed Tuesdays.
A tiny downtown Japanese takeout counter, no seating, just fresh teriyaki with homemade sauces that locals have leaned on for years.
A downtown taqueria slinging tacos, burritos, and Mexican plates, a quick no-fuss local standby with a second spot on Ellsworth.
A downtown spot for Mexican and Salvadoran home cooking, from enchiladas salvadoreñas and carne guisada to super tacos and shrimp burritos.
An industrial-chic downtown cocktail lounge with house-made syrups and Indian-inspired drinks like the Bangalore Old Fashioned, plus Curry Up Now street food alongside.
A downtown lounge and late-night spot with drinks, DJs, and events just off B Street.
Lively downtown sports bar with karaoke on Wednesday and Friday nights plus trivia, in the old Moon's Family Sports Pub space on B Street.
Downtown donut counter beloved for its apple fritters, plus coffee and bagels.
Nagoya-style brothless abura soba (oil noodles), listed in the Michelin Guide.
Hong Kong-style desserts and late-night snacks with a 1960s-nostalgia feel, reopened under new owners in 2026.
Build-your-own spicy malatang hot-pot soup, priced by the weight of what you pick.
The Half Moon Bay brunch favorite brought its American diner classics to the Brickline building on B Street downtown.
Binchotan-grilled yakitori and skewers, small plates, and tonkotsu ramen, in a cherry-blossom room with a karaoke lounge. Open late.
A sixteen-acre downtown park with a 1960s Japanese tea garden and koi ponds, a kids playground, and tennis courts. The beloved miniature train that ran here since the late 1940s is retired for now while the city looks for a replacement, but the garden and playground keep it a downtown favorite.
A downtown indoor playground for kids up to about ten, with slides, a zipline, and obstacle courses.
The city's main library branch with a big children's area, story times, and free community programs near downtown.
Free outdoor concerts in Central Park on summer evenings, a San Mateo tradition of blankets, picnics, and live bands under the trees.
A twelve-screen downtown movie theater within walking distance of B Street's restaurants and parking garages.
A walk-in paint-your-own-pottery studio where families pick bisque pieces and glaze them for kiln firing.
A European-style art school teaching academic drawing, painting, and ceramics to kids and adults.
Salsa, bachata, hip-hop, and Zumba classes plus social dance nights, right downtown.
An artist-run gallery, boutique, and oddities shop that also runs adult and kids art classes.
A boutique of clothing, jewelry, housewares, books, and gifts, much of it from California makers.
A skate shop and art gallery since 2007 with boards, shoes, apparel, and curated streetwear.
The oldest continuously running Asian American bookstore in the country, a nonprofit selling books and educational materials since 1970.
A specialty shop for Gunpla model kits and imported anime figures and merchandise from Japan.
A small-batch chocolatier of fifteen-plus years making handcrafted chocolates and gift boxes.
A baby and kids boutique focused on ethically made, eco-friendly clothing and accessories.
A longtime downtown florist with fresh arrangements, plants, and gifts.
A downtown boutique of timeless, organic, ethically made clothing for babies and kids, with in-store gift wrapping.
A family-owned downtown jewelry store operating since 1937, offering fine jewelry, watches, repairs, and gold buying.
A family-owned downtown San Mateo jeweler specializing in custom design, stone setting, and jewelry and watch repair.
A downtown B Street gift shop selling K-pop merchandise, Sanrio items, Asian beauty products, plushies, and accessories.
A longtime market selling Hawaiian and Asian groceries and prepared foods like Spam musubi and poke.
A family-owned Japanese grocery established in 1980, known for fresh sashimi, seafood, produce, and prepared bento.
A full-service Latin supermarket with an in-house tortilleria, carniceria, Mexican bakery, and aguas frescas in downtown San Mateo.
A downtown produce market stocking fresh seasonal fruits and vegetables alongside European and international specialty groceries.
A Turkish and Mediterranean market and cafe carrying halal goods, fresh baklava, pickled vegetables, and made-to-order borek and gozleme.
A small corner grocery focused on Indian spices, pantry staples, and pooja items in downtown San Mateo.
An appointment-style shop where independent barbers specialize in current cuts and fades, open Tuesday through Saturday.
A full-service salon offering hair, nails, and body treatments under one roof, run by stylists with decades of experience.
A physician-founded healing center that blends modern medicine with ancient practice, breathwork, yin yoga, meditation, sound healing, and ketamine-assisted therapy.
An established studio running more than sixty-five weekly classes across Iyengar, flow, restorative, prenatal, and kids' yoga since 2008.
A full-service salon and spa since 2018, color and balayage, cuts, nails, facials, and scalp treatments, using natural green products.
A family dental practice offering same-day crowns, Invisalign, implants, and sedation dentistry for all ages.
A family-owned optician since 1958 with a curated selection of Japanese and European frames and an in-house lens lab.
A family-owned, full-service lock and safe shop operating in San Mateo since 1927, with a downtown storefront and mobile service.
A long-running walk-in barbershop in downtown San Mateo known for classic cuts and straight-razor work.
An acupuncture and herbal medicine clinic in downtown San Mateo, founded in 2000.
A downtown San Mateo optometry practice providing eye exams, contact lens fittings, and eyewear since 2005.
More added every week. Spotting something missing? Suggest a spot. · Own a business we're missing? Get listed, free.