Hunting Down Oakland’s Best Dive Bars During The City’s Cocktail Week

Keyla Vasconcellos

It’s no secret that Oakland, the larger of the East Bay cities, is in the throes of a new culture wave. The city has become a mecca for burgeoning new restaurants and bars and boasts an incredibly distinct food scene. While gentrification is an issue people are actively wrestling with, the soul of Oakland seems to have come this far unscathed. The locals exude fierce pride in their big city with small-town vibes, where diversity, inclusivity, and a sense of history are revered.

Recently, Oakland’s first ever Cocktail Week showcased its growing bar culture and drew guests from around the Bay Area. Although you’ll find plenty of listicles online highlighting where to eat or drink in Oakland, this week’s action was centered on the smaller neighborhood bars — where locals gathered, warmly chatting with friends and newcomers alike over a cocktail. To illustrate their community connectedness, most storefronts displayed “Oakland Stands United Against Hate” posters around town.

I arrived in Oakland in style with JetSuiteX, which provided a super Instagram-worthy flight from Burbank. If you’re going off to a new city to drink for a week, this is a pretty solid way to do it — it was great not having to deal with the hassle of lines and the TSA. Once we were in the air, Cocktail Week started early with a complimentary drink that went down as quickly as the hour-long flight. After landing and checking into my hotel, I left for the first event: Town Spirit: A Tribute to Oakland’s Enduring Bar Culture.

The Town Spirit event took place at the Oakland Museum, where guests took their seats to watch a short documentary followed by a reception with light food and cocktails. The film captured the essence of Oakland, which, despite significant gentrification and the skyrocketing cost of living, has managed to preserve its cultural identity and maintain its old-school drinking institutions. After viewing the film, I knew I had to ditch my plans to explore the new-age cocktail scene and instead discover the best dives Oakland’s community-driven neighborhoods had on offer. Here are several affordable, dark, iconic watering holes — the kind where you feel welcome as soon as you walk in the door.


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Entering Café Van Kleef almost feels like walking into a tchotchke museum, where a game of “I spy with my little eye” would keep you entertained for hours. It’s dark, resembling your typical dive, but filled with timeless treasures including paintings and random relics, giving the place tons of character.

Besides being around for over 15 years, Café Van Kleef is known for its Greyhounds with freshly pressed grapefruit juice that compliments the generous vodka pour, with a cartoon-sized grapefruit slice as the garnish.


The Ruby Room is your go-to for a seedy, affordable dive. The dim red lights keep the place dark – the perfect gateway to bad decision-making. You’ll meet some characters along the way and will probably forget your credit card, but you’ll have some great stories by the end of the night. After all, how else are memories are made?


You just can’t go wrong walking into a piano bar with talented singers belting out classics and your favorite spirit being poured. The Alley opened in 1933, and serves as a reminder of simpler times without electronics and social media. You’ll find comfy booths, traditional American fare, and over 40,000 business cards surrounding the space – an homage to those who have come and gone and imbibed at The Alley.


Heinolds’ First & Last Chance Saloon is a historical landmark that has been around since 1884. There might be some argument over whether or not it’s a dive, but it’s a unique and dimly lit bar that cannot be missed while in Oakland. It’s the city’s original saloon at its original site and sits within the Port of Oakland. It adopted the pseudonym ‘First and Last Chance’ when sailors would leave to go overseas back in the day; it was essentially the place for all “comers and goers” to grab a drink.


Starline Social Club is a bar that’s not comparable to any of its senior establishments, yet it’s situated in a historic 1893-era Victorian. The space has had many lives including a saloon, social club for the deaf, and home to Starline Janitorial Supply. Now, you’ll find a unique bar program, food pop-ups, and dance parties. As you head downstairs to the epicenter of the space, you can expect to find events highlighting diverse musicians as well as artists, activists and entrepreneurs focused on community building.


Although the Polynesian-themed restaurant Trader Vic’s has expanded all over the world, it was born in Oakland in 1934. Originally named Hinky Dink’s, 32-year-old Trader Vic was ahead of his time, creating the first Mai Tai with generous pours of light and dark rum, orgeat syrup, lime juice, and orange Curacao. Check out the Trader Vic’s headquarters (now in neighboring Emeryville) and unwind, as you pretend you’re somewhere tropical. Remember to cheers to the “Home of the Original Mai Tai.”


In the documentary portion of the Town Spirit event, Andie Ferman, a fixture in the Bay Area spirits scene, mentions that even with all the recent change in Oakland, these drinking institutions have upheld the flavor of the old city:

“I think it’s important when we have new blood, new bars, new restaurants moving in, that these bars that have been here and held true, we need to make sure they are still here for years to come. Because they have definitely informed what is now the new cocktail movement. ‘The new Oakland.’ Without the root system, the tree is going to fall. So it’s really important to support these bars, so they can continue.”

It’s a worthwhile sentiment for a city in the midst of such rapid upheaval to consider. And it’s not a big ask, either — considering how incredible the drinks at each establishment are.

Flight paid for by JetSuiteX. Read the Uproxx press trip policy here.