The Hippest Place to Be
Think "hip, up-and-coming city in the U.S." and there's a good chance Oakland will immediately come to mind (that or perhaps its East Coast sister, Brooklyn). The city has always been cool — home to diverse residents, multicultural cuisine and natural sights — but increasingly, it's been adding more quintessentially Oakland attractions to the mix, and the masses are catching on.
The city offers a cultural urban vibe that, compared to its pricey neighbor of San Francisco, is enjoyable on a budget. But the real heart and soul of Oakland is its locals — warm, friendly and abundantly creative. Look around, and you may spot them busking, guitar-strumming or decorating the city with brilliant, socially conscious street art. After visiting, you might very well decide to stay forever, too.
Experts Weigh In
Staying forever is exactly what Jessie Fetterling and Diane Tadano have decided to do. Both have lived in the city for several years, and are bona-fide experts on all it has to offer.
Jessie is such a fan of the city, she penned the guidebook "100 Things to Do in Oakland Before You Die," available on Amazon. A travel aficionado by passion and trade, she has written about wanderlust for Where San Francisco, TravelAge West, Prevue, Diablo and Time.com.
Diane is the manager of one of Oakland's most Oakland-y haunts: the New Parkway Theater, which connects locals and visitors to the community through Doc Nights, film festivals, special screenings and Karma Cinema, which kicks back part of ticket profits to local nonprofits.
We asked both to select their Oakland faves, so even those stopping in for a few days can feel like a tried-and-true local.
Best Place to go for Live Music
The Fox Theatre; New Parish; Starline Social Club; Yoshi’s
Jessie has seen such hot indie acts as Jenny Lewis, The Devil Makes Three, Yonder Mountain String Band, Spoon and Talib Kweli perform at the historic, extremely popular Fox Theatre downtown. But, she says, “I also have to give a shout-out to the New Parish and Starline Social Club, both of which know how to highlight the local music scene.”
Diane has enjoyed the sophisticated sounds of Goapale and Ledisi at Yoshi’s, a classy jazz club-meets-sushi lounge near Jack London Square.
Best Place to Nerd Out At
Oakland Museum of California
Jessie and Diane agree that this museum is the place to be, giving kudos to its extensive recent Black Panthers exhibit in particular. They also concur that it’s best to show up on a Friday night, when DJs spin music, wine is served and food trucks show up en masse. Jessie calls the scene “quintessentially Oakland and a good taste of the community, in the same way Grand Lake Farmers Market on Friday mornings is, or First Friday events are on Telegraph.”
Diane notes that you can reserve a picnic table outside the museum on Friday evenings, to eat with friends before or after hitting up the exhibits.
Best Fancy Dining Spot
Moa; Camino; Scott’s Seafood
Jessie likes Mua, a high-design tapas restaurant in downtown that’s “upscale but not too crazy experience.” Want something super-fancy? She suggests Camino, which in addition to serving sublime cuisine in a sophisticated space, is quintessentially Oakland in its ethos — it strives for minimal waste and “is really good to its employees,” adding a fair tip to the price of every meal.
When Diane wants an elegant night out, she heads for Scott’s, a waterfront, white-tablecloth favorite. “Everyone’s dressed up here,” she notes — so leave your jeans at home.
Best Cheap and Greasy Dining
Portal; Tacos Mi Rancho taco truck
Jessie can’t get enough of Portal’s cheekily named “garbage bread” — flaky bread stuffed with melted cheese and crispy pepperoni or fresh veggies, paired with marinara and pesto sauces “that add a flavorful kick.” Plus, she says, the restaurant has “a spacious patio that's tucked away from the downtown scene.”
Diane prefers that old Oakland standby: the taco truck. She recommends Tacos Mi Rancho, on the outskirts of Lake Merritt, serving simple, perfectly prepared classics until 2:30 a.m. Act like a local by casually referring to it as “the taco truck on the other side of the lake,” she recommends.
Wildest Night in the City
Downtown bars; warehouse afterparties; The Stork Club
Jessie says any evening that begins with a live-music show at the Fox Theatre inevitably “turns into a wild night,” culminating with closing down bars like Bar 355 and The Legionnaire Saloon downtown. A First Fridays art walk followed by a burlesque show at The Stork Club has also made for late nights/early mornings to remember.
After an evening of downtown bar-hopping, Diane ended one night out at an afterparty in a warehouse, featuring thumping techno and EDM music. “I thought the city shut down!” she says — but such after-hours get-downs are common, if you know how to connect with the right people for an invite.
Greyhound at Cafe Van Kleef
Cafe Van Kleefe’s Greyhound is the clear winner — a perfectly balanced mix of high-quality vodka and fresh-squeezed grapefruit juice, paired with a massive slice of the flavorful fruit.
“They give you basically a third of a grapefruit!” Jesse exclaims. “So it’s a good place to go if you want a snack too.” Diane agrees: “Its not pre-mixed or out of a can; you can see the squeeze in it.”
Best Cup of Joe
Timeless Coffee Roasters; Bicycle Coffee Co.; Philz Coffee
Timeless, Jessie says, is “your typical neighborhood coffee shop where everyone seems to know each other.” They roast their own coffee beans, and serve up a tasty rotating-flavor waffle special. Jessie also loves the laidback vibe of Bicycle Coffee, which includes onsite bike-docking stations for caffeine-craving cyclists.
Diane prefers Philz, which started in the Bay Area and offers an outpost on upscale College Ave. in Oakland. Their secret to success? Customized blends from the highest-quality beans. The dark roast Jacob’s Wonderbar with cream is so satisfying, Diane says, that she’s yet to try the roaster’s beloved cold brews, which are next on her list.
Best Pint of Beer
Our experts agree: Drake’s Dealership is the best in town. Both Jessie and Diane dig its expansive outdoor patio, featuring Adirondack chairs and fire pits. Even more importantly, they can’t get enough of the home-brewed beers. Even though she’s “not usually a fruity beer person,” Jessie loves the not-too-sweet pomegranate brew, which she says is “especially refreshing on a warm Oakland day.” Diane, meanwhile, is a fan of the red ale.
(The beer list is rotating, but you have a good chance of seeing at least one of these on the menu if you go.)
Weirdest Oakland Destination
Beer Revolution; The Kingfish Pub & Cafe; The Alley Karaoke Bar
Beer Revolution is, says Jessie, a “grungy punk bar” that encapsulates Oakland’s edgy vibe; ditto the “funky” Alley Karaoke Bar, adorned with oddball old posters and featuring a live piano player who accompanies locals as they croon songbook standards. The Kingfish is among the best in the genre of “very Oakland, very dive bar,” featuring shuffleboard, cheap beer and free popcorn.
Diane singles out Chinatown, but notes “it’s not weird, but different. In so many other areas, it doesn’t necessarily feel like you're in a different neighborhood. But you know you’re in Chinatown when you’re in Chinatown.” A self-described “street shopper,” Diane likes perusing the shops, ordering Vietnamese sandwiches and sipping on boba bubble tea.
Sports Team to Root for (And Sports Team to Hate)
Golden State Warriors; Oakland A’s; Oakland Raiders
No surprise here: Jessie and Diane are fans of the Warriors, Oakland’s beloved NBA team. (Go Dub Nation!) “It’s exciting because they’ve won a bunch of championships in the last couple years,” Jessie notes, not entirely hyperbolically. (They won the NBA Finals in 2015 and 2017.)
Diane also roots for the NFL’s Raiders and, with that, boos their rival teams: the Denver Broncos (“They’re in the same division, so if they do well, we don’t do well”), Dallas Cowboys and Los Angeles Chargers. Want to save money? “The (MLB) A’s have the best ticket prices — it’s the most affordable thing to watch,” Diane says.
Still, both are quick to point out that with the Warriors soon moving to San Francisco and the Raiders to Las Vegas, sports fervor is likely to fade. “It’s a pretty big hit to Oakland,” Diane laments.
Best Spot for a Day Trip
Muir Beach; Muir Woods; Tilden Park
Jessie likes to head north to Muir Beach, featuring quiet coastline surrounded by wilderness, and Marin Headlands, a hilly peninsula overlooking the dazzling Pacific Ocean and Golden Gate Bridge. “The perfect day is going hiking in the headlands, then grabbing a glass of wine or pint of beer at Pelican Inn, an English pub in the middle of nowhere,” she says.
Diane also enjoys the North Bay, recommending Muir Woods, home to ancient towering redwoods. Closer by, in Oakland's next-door-neighbor Berkeley, she likes to venture through Tilden Park. “I just start walking around on random trails,” she says. “Then I try to to get to the top of something by just climbing.”
Best Birthday Locale
Piedmont Springs; Caña Cuban Parlor and Cafe; local food bank
For a romance-infused birthday with your partner, Jessie suggests Piedmont Springs, where you can rent out hot tubs carved from redwood, and luxuriate in your own private patio area fenced out from the one next to it. The result, she says, is an “escape-from-it-all sense of relaxation.”
For a group get-together, Jessie suggests Caña Cuban Parlor and Cafe, which features not only delectable eats — think fried chicken and succulent Cuban pork — but Sunday salsa dancing.
Or, to really act like a local, take part in the city’s proud cultural tradition of do-goodery. Diane spent her last birthday helping out the community. “I took my family to a food bank, asked my friends to bring toiletries that we bagged, and then we all cleaned up a local park. I didn’t need to go out to eat — I wanted to make a difference.”
Where to go on a Rainy Day
Grand Lake Theater; New Parkway; Plank; The Terrace Room
The Grand Lake Theater, Jessie says, has “stood the test of time”; dating back to 1926, it still features a classic marquee, ornate decor and, every Friday and Saturday night, the musical stylings of a live organ player. Plus, Jessie notes, “its ticket prices are a bargain by today's standards.”
Alternatively, she suggests heading to Plank in Jack London Square for arcade games and bowling. (When it’s not raining, the venue also offers outdoor bocce ball courts.)
Diane says the “huge window overlooking Lake Merritt” at The Terrace Room restaurant is perfect for watching the rain without getting drenched. Or, she says, people should head to The New Parkway (“obviously!”) to select from mainstream hits, classic films and quirky oddities.
Best Place for Adventure
Redwood Regional Park; Lawrence Hall of Science
When Jessie wants to satiate her local wanderlust, she heads for the woods — Redwood Regional Park, to be exact. “This is one of my favorite spots to hike in the East Bay because you can see the area's famous redwood trees without making the trek to Muir Woods or way up north to other better-known redwood forests,” she says.
Though she hasn't been in 15 years, Diane can't stop thinking about her trip to Lawrence Hall of Science, in nearby Berkeley, perched in the hills above the skyline of Oakland and San Francisco.
Why Oakland is Objectively the Best City on Planet Earth
“It’s not pretentious in any way,” Jessie says. “And it has a really strong sense of community and history, with an interesting meld of people.” After years in San Francisco’s shadow, she says, “it’s time for Oakland to really shine.”
Diane loves that the city “offers everything for everyone. Want a big city feel? You can create moments around big city items, with popular bars and touristy places and mainstream shopping. At the same time, there’s a local feeling — you can be in a neighborhood where everyone knows all their neighbors, and where they go to local watering holes where everyone knows their name.”