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Oakland is no harmonious melting pot, not currently at least. For many years, hip-hop, punk, biker and hippie subcultures had managed to live there together without incident (aside from, you know, some rioting). But today, the success of Silicon Valley has encroached on the East Bay. As San Francisco has priced out young techies, they’ve infiltrated Oakland in search of cheaper real estate. Cue the tension. The new Oaklanders want to make the city in their image, as when Manhattanites crossed the East River to create the Brooklyn we know today. While locals might benefit from the influx of tech money, the gentrification has left longtime residents jealously guarding their neighborhoods, parties and bars from the tech crowd. Today, the fight for Oakland’s soul has grown even more intense—wealthy newcomers on one side, rough-and-tumble old schoolers on the other. The divide, however, can be navigated—at least if you’re just visiting—with both factions providing plenty of reasons not to pick a side.

3 P.M. You’ve just gotten off the BART (Bay Area Rapid Transit to the uninitiated), and you aren’t sure you’re in the right place. Was the stop “Civic Center” or “City Center”? Why is nobody in the agent booth? Guess what? You’re on your own. Oakland is a city that strongly abides by survival of the fittest. Walk up the first steps you see—because the escalator is broken. If you got off at “City Center,” welcome to Oakland. (If you got off at “Civic Center,” you’re in San Francisco, the wrong side of the Bay Bridge and a place where Oaklanders rarely wander.)


3:12 P.M. The region orients itself largely in relation to the Bay, but a day in Oakland requires getting familiar with a lake. Walk east on 12th Street from the City Center BART stop until you hit the southern edge of Lake Merritt. In 1870, the small lake (its circumference measures 3.4 miles) made history as the country’s first wildlife refuge. Surrounded by the diverse, family oriented Grand-Lakeshore neighborhood, there are a lot of great restaurants and bars, despite the number of strollers. On the lake’s north side is Children’s Fairyland, America’s first theme park, which helped inspire Walt Disney to design Disneyland. It’s a great place to go with kids or experience while tripping balls.

3:45 P.M. A short walk past Fairlyland is Los Cantaros, a counter-service taqueria that’s perfect for grabbing lunch to go. Order the super burrito—a flour tortilla stuffed with beans, sour cream, cheese, guacamole (ask for extra, it’s awesome), homemade salsa and your choice of meat (choose steak). All of the aguas fresca are good, but the watermelon stands out above the rest.

4:27 P.M. Follow the lake around a little farther clockwise to Heart and Dagger Saloon. While it might not be the local equivalent of Switzerland, it’s relatively neutral when it comes to welcoming the new breed and old schoolers alike. Be forewarned: It isn’t a place for artisanal cocktails. If you dare order a drink with more than two ingredients, a bearded, tattooed bartender named Hicksmokey will pour you a shot of whiskey instead (possibly in a pint glass) and then yell “Put it in your boozehole!” until you finish it.

6:49 P.M. Once you’ve completed the lap around Lake Merritt and you’re back near City Center, venture inside the Ruby Room (sister bar to Hollywood’s delightfully grungy dive bar, the Burgundy Room). New money would love to turn this prime location into a spot for mixologists and Bon Iver fans; locals pray it will never happen. Scarlet bulbs light most of the Ruby Room—meaning nobody can see well enough to care what anybody looks like. The six-foot-two leather-clad co-owner, who also happens to be the president of East Bay Rats Motorcycle Club, might be around, and he’s perfectly friendly. He has staffed the place with competent and only slightly surly bikers and punks. Order a drink and get enveloped in the punk, rock, goth and nu wave blaring over the speakers. If you want to finish your drink, don’t make any music requests.


8:10 P.M. Your taste of New Oakland starts with dinner at Flora. The restaurant serves new American fare in a 1930s art-deco building that inspires its interior decor, and its penchant for reimagining, early 20th century cocktails. Order the filibuster; it isn’t always on the menu but the bartender will gladly make one for you—it is, more or less, George Dickel whiskey mixed with maple syrup, lemon, egg white and bitters. For an appetizer, get the house-cured king salmon lox and potato cake. It’s delicately plated to display the bright colors of the fish, which is accompanied by an apple-radish salad, a Bartlett pear sauce and crème fraîche. For the main course order the burger. It may sound boring but the grass-fed beef is ground in house cooked to perfection and then topped with aged cheddar and caramelized onions. End the meal with the spiced Bartlett pear tart that comes with bourbon cream and a roasted-pear sorbet.

10:36 P.M. Hit the Uptown Nightclub on the right night and you’ll be treated to a great show. Every Monday, with some Fridays and Saturdays sprinkled in, the bar hosts the Hubba Hubba Revue, the Bay Area’s premier burlesque show. Feel free to marvel at Lady Satan, the sassy, irreverent dancer; Balla Fiya, who’s curvy, sexy, and does things with feather fans that will make you sweat; and Kara Nova, a fit and gorgeous acrobat. Even if the revue isn’t performing, there’s plenty more entertainment—from the Rocket Queens (a Guns N’ Roses tribute band) to Uptown Boogie (a dance party where a DJ plays funk and hip-hop jams from Parliament to Tone Loc).


1:45 A.M. It’s a quick cab ride from the Uptown to Home of Chicken and Waffles. Located in Jack London Square, this family-owned and -operated spot has a 1960s diner look but a soul-food-heavy menu. Each dish is named after a family member and each family member is commemorated—holding their eponymous meal no less—on the murals decorating the restaurant’s walls. But don’t complicate things. Stick to the part of the menu that’s all chicken and waffles. The waffles are covered in butter and the chicken is tender, providing the perfect combination of sweet and savory.

3:08 A.M. The nearby Waterfront Hotel beckons. As its name suggests, the hotel is located on the waterfront, along Oakland Inner Harbor. This boutique hotel doesn’t break the bank, and it provides clean rooms, good service and a nautical theme with a touch of kitsch. Solid but not fancy features, welcoming and less expensive than its neighbors? Sounds like quintessential Oakland.


This article was originally published on Playboy for iPhone. For more exclusive content and the best articles from the latest issue of Playboy, download the app in the iTunes Store.


Jade Hoffman is a Bay Area blogger. Follow her on Twitter at @whiskeypants.

Photo by Zoe Nauman

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