Silicon Valley by Night: an Insider Guide to San Jose

With improv, jazz jams, wine bars and night markets all clamoring for your attention, an evening out in San Jose is always an adventure. Discover the dynamic world of Silicon Valley as it lights up at night, from upscale video game bars to one of the most haunted houses in the world.

There’s nothing quite like sipping on a rich Californian red in California. So, where better to sample the local tipples than the Vintage Wine Bar? Step through the stone-arch entrance on Santana Row, order grazing plates and prepare for a wine experience like no other. Oenophiles are unsurprisingly well catered for, with grape varieties from across the globe. But don’t fret if wine isn’t your thing, the whisky menu will take you on a whirlwind journey from the US to Scotland. And if you try something you love, pick up a bottle (or two) from the adjoining store as a memento.

To really get under the skin of Silicon Valley, you need to eat your way around. So head straight to the source: San Pedro Square Market. Open until midnight, this free-to-enter dining destination hosts some of the best restaurants in the city, from seafood and pizza to all-out American burgers. Entertainment is never far away – lilting live music provides the perfect stall-sampling atmosphere. Don’t leave without trying the locally loved Loteria Taco Bar for expertly made Mexican food, a cold beer and some people watching.

A far cry from the Silicon Valley tech bubble, Winchester Mystery House is certainly the spookiest way to spend a night in San Jose. This mansion on South Winchester Boulevard was once home to Sarah Winchester, a wealthy widow who renovated and extended the property from 1886 to 1922. After her death, rumors of paranormal activity swirled. Harry Houdini even visited to debunk the stories (to no avail). Test your mettle and take the Flashlight Tour, an after-hours self-guided wander through this hunted building.

In the heart of buzzy Downtown, San Jose Improv is a comedy club with a difference. History lovers take note: it was built in 1904 as a hub for vaudeville acts and is the oldest theater in San Jose. Loved by Silicon Valley locals for its casual and welcoming vibe, the Improv hosts a smorgasbord of comedic talents, from up-and-comers to big-name stars. Score a comfy booth, order a pizza from the club bar, and spend the evening cackling to stellar acts.

For a dose of Americana, cruise straight to the West Wind Capitol Drive-In on the edge of town. Movie nights don’t get more nostalgic than this: simply park up by one of the screens and devour a bucket of popcorn while the movie blasts through your car speakers. Three screens and multiple showings per day – new releases and classics – ensure there’s a film to satisfy everyone. Better yet, you can bring your own food, so it’s worth stopping by the San Pedro Square Market ahead of curtain call.

An evening in San Jose just isn’t complete without live music. To get your fix, make your way east to JJ’s Lounge. A little rough around the edges (like all good dive bars), JJ’s has spent years earning its reputation as the home of traditional jazz in Silicon Valley. Stop in after a dinner in Downtown, order a drink from the vast Japanese whisky collection, and settle into an empty corner to enjoy the show. In between sets, stake your claim at the vintage pool table, it’s a dive bar right of passage.

When staying in San Jose, it seems only right to revisit Silicon Valley’s roots. Unleash your inner gamer at Guildhouse, an upscale entertainment destination near San Jose State University. Rent PCs and other consoles by the hour, load up an RPG and enjoy interactive gaming the way it was meant to be experienced – socially. Large open spaces are reserved for tabletop gaming, while the bar and kitchen serve home comforts, local beers and craft cocktails. Each food order bags you an extra hour of play, so don’t be surprised if your virtual adventure keeps you up until midnight (better known as closing time).

Find out more and start planning your trip now by visiting visitcalifornia.com/road-trips