Five Points Cocktail Bar (Bowery Room) is a nightlife spot in Downtown, San Jose.
Five Points is one of downtown San Jose's top craft cocktail bars, with a hidden Bowery Room speakeasy in the back featuring exposed brick and a marble bar.
Editorially verified June 26, 2026 by Lewis Vaughan, TableJourney editor. Source.
Tip: The Bowery Room opens at 9pm Friday and Saturday; arrive early to claim a table in the tucked-away speakeasy. Free jazz jams Monday nights.
Address: 169 W Santa Clara St, San Jose, CA 95113
Paper Plane is a sophisticated craft cocktail bar in downtown San Jose open since 2013, known for one of the Bay Area's largest curated spirits collections.
Tip: The bi-annual rotating cocktail menu rewards repeat visits; ask bartenders to guide you through obscure spirits you've never tried.
Mac's Club is San Jose's oldest LGBTQ bar, a welcoming neighborhood dive serving the LGBTQIA+ community since the 1950s with strong drinks and a back patio.
Tip: The low-key outdoor patio is a local favorite for evening drinks; Mac's hosts occasional Pride season events and is cash-friendly.
Voted Silicon Valley's top gay nightclub, Splash has two dance floors, a rooftop patio, 20-plus video screens, and weekly drag shows in downtown San Jose.
Tip: Drag Bingo Monday nights is a community staple; the rooftop patio fills fast on warm weekend nights so arrive early.
The Hedley Club at Hotel de Anza is San Jose's premier art-deco lounge with live jazz Thursday through Saturday in a beautifully preserved 1930s room.
Tip: Live music also runs the 1st and 3rd Wednesday of each month; the seasonal cocktail menu and wine program are among the best curated in downtown San Jose.
Five Points is downtown San Jose's craft cocktail bar, hosting free live jazz jams every Monday night in its intimate Penny Room with San Jose Jazz.
Tip: Jazz jam starts at 9:30pm Mondays with a concert set at 8:30pm; free entry and open bar menu make this the best value listening night in the city.
Paper Plane is a sophisticated craft cocktail bar in downtown San Jose open since 2013, known for one of the Bay Area's largest curated spirits collections.
Tip: The bi-annual rotating cocktail menu rewards repeat visits; ask bartenders to guide you through obscure spirits you've never tried.
Mac's Club is San Jose's oldest LGBTQ bar, a welcoming neighborhood dive serving the LGBTQIA+ community since the 1950s with strong drinks and a back patio.
Tip: The low-key outdoor patio is a local favorite for evening drinks; Mac's hosts occasional Pride season events and is cash-friendly.
Voted Silicon Valley's top gay nightclub, Splash has two dance floors, a rooftop patio, 20-plus video screens, and weekly drag shows in downtown San Jose.
Tip: Drag Bingo Monday nights is a community staple; the rooftop patio fills fast on warm weekend nights so arrive early.
Dr. Funk is a rum-focused tiki bar in San Jose's San Pedro Square, channeling 1930s escapism with fresh-juice cocktails and a welcoming, inclusive crowd.
Tip: The Rum Club membership unlocks special releases; tiki cocktails are built with house-made syrups and fresh citrus, not mixes.
The Hedley Club at Hotel de Anza is San Jose's premier art-deco lounge with live jazz Thursday through Saturday in a beautifully preserved 1930s room.
Tip: Live music also runs the 1st and 3rd Wednesday of each month; the seasonal cocktail menu and wine program are among the best curated in downtown San Jose.
Five Points is downtown San Jose's craft cocktail bar, hosting free live jazz jams every Monday night in its intimate Penny Room with San Jose Jazz.
Tip: Jazz jam starts at 9:30pm Mondays with a concert set at 8:30pm; free entry and open bar menu make this the best value listening night in the city.
