Cocktail bars, a German beer hall, Irish pubs, wine bars, cafés, and live-music rooms, all a short walk from Caltrain. Places with something on tonight come first.
Large Irish pub and restaurant in a historic building off Broadway. Hosts weekly pub trivia, Bay Area games on the TVs, and occasional cover bands.
↻ Pub Trivia: Every Thu, 7:30 PM
↻ Speak Easy Monday: Every Mon
↻ Friday Live Music: Every Fri, 8:00 PM
+ 1 more every week
Historic 21+ music club next to the Fox Theatre, with shows most Thursday through Saturday nights. Tribute bands, blues, funk, and occasional comedy, mostly general-admission.
↻ First Thursday Blues Series: 1st Thu monthly, 7:00 PM
Craft cocktail lounge across from Blacksmith, open since 2018. Known for seasonal cocktails and molecular-mixology labs, with live music or DJs on weekend nights.
↻ Live Music & DJs: Every Fri & Sat, 9:00 PM
↻ Soft Jazz & Smooth Whiskey: Every Thu, 8:00 PM
Old-school lounge on El Camino with karaoke Thursday through Saturday, a free pool table, and a jukebox, on the edge of downtown.
Couldn't confirm current hours. Call ahead.
↻ Karaoke Nights: Every Thu & Fri & Sat, 9:00 PM
Latin-inspired tapas and cocktail spot next to Blacksmith, with brunch late in the week and a lounge that turns into a late-night party on Friday and Saturday nights.
↻ Lounge Party Nights: Every Fri & Sat, 9:30 PM
Family-owned 'upscale dive' modeled on Lafitte's Blacksmith Shop in New Orleans, with an open hearth, craft cocktails, and a patio. DJs spin on weekends, and Thursday is karaoke.
↻ Karaoke Thursday: Every Thu
↻ Weekend DJs: Every Fri & Sat
An elegant but unpretentious lounge on Brewster Avenue near El Camino, with more than 35 wines by the glass from the West Coast and beyond, cocktails made with fresh-squeezed juice, and small bites.
Couldn't confirm current hours. Call ahead.
Supper club and restaurant with a stage, long known for jazz, cabaret, and dinner shows. There's a weekday happy hour at the bar.
Flower shop on Winslow Street with a coffee bar tucked inside, where you can sip a latte among buckets of fresh blooms.
Low-key locals' bar around the corner from the Fox Theatre, with NFL Sunday Ticket, a big screen, and about 21 drafts.
Couldn't confirm current hours. Call ahead.
Weekday coffee and breakfast counter at the San Mateo County government center, with sandwiches, a daily lunch special, and catering for county offices.
Couldn't confirm current hours. Call ahead.
Micro-roastery on Main Street with an outdoor espresso bar, a pour-over menu, and breakfast and brunch plates to eat on the patio.
Roomy cafe in the old Young's Ice Cream building, a short walk from Caltrain. A popular laptop-and-hangout spot that also pours beer and wine.
Mexican-style coffeehouse in the former Cyclismo Cafe space, pouring Chiapas coffee alongside pan dulce, giant conchas, and seasonal drinks.
Venezuelan-rooted Peninsula coffee chain on the ground floor of the Marston building, with all-day breakfast, arepas, and sandwiches, plus beer and wine.
Wine-and-beer bar with a bottle shop in the former BottleShop space, aiming to be a neighborhood living room. Has hosted Peninsula Comedy stand-up nights since summer 2026.
↻ Raclette Night at de Vine: Every Wed, 5:00 PM
Bar and kitchen on Main Street serving brews, signature drinks, and premium liquor, with a weekly early-evening trivia night.
↻ Trivia Night: Every Wed, 6:00 PM
↻ Creative Meet-UP Bay Area: 1st Thu monthly, 6:30 PM
Family-run Bavarian bierstube, German market, and bottle shop open since 1975. Pours German drafts in liters, with pretzels and sausages in the beer garden.
Bar by the Caltrain station with 20 rotating NorCal taps, 400+ spirits, and Indian-fusion cocktails. Pizza comes from Curry Pizza House next door, and there's a pool table and dog-friendly patio.
Smoothies and fresh juices in Sequoia Station, plus açaí bowls, oatmeal, and snacks for a quick breakfast near the train.
Coffee lounge with its own street entrance in the rebuilt Rise City Church, from the team behind San Mateo's Kaizen & Coffee. Latin-inspired drinks like a panela latte and mango matcha, with Amour Bakery pastries.
Parisian-style patisserie on Broadway with croissants, tarts, and cakes, plus a short menu of breakfast and lunch plates and coffee to go with them.
Latin nightclub on the south end of Broadway that books regional Mexican and Latin concerts and dance nights.
Berkeley-born coffee chain at the El Camino end of Broadway, with warm breakfast items, pastries, and free Wi-Fi for commuters walking from Caltrain.
Made-to-order pour-overs from the San Francisco coffee company, including the minty Mojito iced coffee, on Broadway steps from Courthouse Square.
Yemeni coffeehouse at Broadway and Winslow pouring spiced Yemeni coffee, pour-overs, and cardamom-scented Adeni tea, with pastries on the side.
Members-only music clubhouse with rehearsal studios and a stage, running hosted weekly jams like Three Chord Thursday. Membership is required (21+), but drop-in tours are offered.
Coffee chain counter in Sequoia Station, steps from the Caltrain platform, with espresso drinks, breakfast sandwiches, and pastries for commuters.
Coffee chain counter in the Peninsula Boardwalk center at Veterans and Walnut, with espresso drinks, breakfast sandwiches, and pastries.
Deli near Maple St with a long sandwich board: Cubano, Reuben, Godfather, mango habanero chicken, and eggplant parmesan, plus classic cold cuts, salads, and coffee.
Couldn't confirm current hours. Call ahead.
European-style bakery and café on Main Street, opened in 2024, baking its baguettes, breads, and croissants on site. Go early for the best selection.
Two-level pub and performance space with a New Zealand-inspired kitchen in the old Underground Pub spot. Its weekly lineup includes an open mic, band jams, and board games, plus monthly burlesque.
↻ Open Mic Night: Every Tue, 6:30 PM
↻ Band Jam Night: Every Tue, 8:30 PM
↻ Board Game Night: Every Thu, 7:00 PM
+ 1 more every week
Irish pub that replaced longtime City Pub in June 2025. Keeps about 24 taps of mostly Bay Area beer, adds low-ABV cocktails and Irish comfort food, and has a patio.
↻ Tuesday Trivia: Every Tue, 7:00 PM
↻ Bar Bingo: Every Sun, 6:00 PM
Espresso and pastries in the historic Offerman House, downtown's oldest surviving building, with indoor seating and a garden-style yard that hosts community events.
↻ Community Craft Circle: Every other Sun, 12:00 PM
↻ Jane Austen Reader Theater: 1st Thu monthly, 6:00 PM
↻ Micro Market: 1st Sat monthly, 9:00 AM
+ 5 more every week
Steak-and-seafood restaurant whose bar is a draw on its own, with house syrups, bitters, and a zero-proof list. Happy hour runs Tuesday through Saturday.