Oakland Rising: How to Spend a Perfect Day Across the Bay

·Associate Travel Editor
image

Paul Hayward, a San Francisco resident who opened Overland Country Bar & Restaurant in Oakland this year. (Photo: Greg Keraghosian)

When it comes to Oakland and its longtime residence in San Francisco’s shadow, I am part of the problem. I’m an SF native and resident who for years has chosen 30-minute bus rides to the Mission District’s eternally cool bars over shorter subway rides to Oakland’s more recently cool attractions. I wrote an article stating exactly why San Francisco is better than Oakland. I can think of one or two times I ventured to Oakland all of last year.

Why? Because I live in San Francisco! Why drive a Mustang when you can drive a Ferrari? Especially when you’d rather not drive at all and the BART trains stop at midnight?

I recently gave in and agreed to play Snob Cinderella by spending an entire day in Oakland on a sort of dare, letting the city show me its best until the clock struck 12 on a day that included a farmer’s market, kayaking, and jazz. Near the day’s end, I was surprised to identify most with a San Francisco resident who runs an unironically cheesy country bar with frozen margaritas and line dancing in the most touristy part of town. And I found that what won him over could someday compel me to move there.

image

My San Francisco Giants hat and I don’t spend much time here in Oakland’s Jack London Square. (Photo: Greg Keraghosian)

“I think San Francisco is the best city in the world,” said Overland Country Bar & Restaurant’s owner, Paul Hayward, when I asked him about opening in Oakland’s Jack London Square this summer across the bay from his home, where he’s lived since 1996. “But it’s insufferable.

“Everyone’s become grumpy with the standard of living. It’s not a great place to live anymore. Oakland is friendlier and it’s way more diverse. I’d move here in a heartbeat if I didn’t have such a sweet [housing] deal.”

I may play hard to get, but I’ve secretly wanted to be seduced by Oakland as he was – there’s still a lot to love, but San Francisco’s insane housing costs plus the encroachment of tech bro culture has weakened our quirk and community, spawning a delicious-yet-homogenous array of upscale New American restaurants and craft cocktail bars. Paying $20 or more for a burger is not unheard of, and affordable ethnic restaurants (not to mention ethnic people) are getting squeezed out by raised rents. The Brooklyn-Manhattan analogies don’t fully work here, but it’s safe to say that San Francisco has lost some of its edge and creative people to Oakland. (And yes, I totally realize that I work for a tech company, too.)

There are reasons why San Francisco will always be called “The City” on both sides of the Bay Bridge: Oakland will never win a beauty contest against San Francisco’s skyline and landmarks; it still has a reputation for being dangerous; and it’s facing gentrification issues that could lead to its own hipster backlash. There’s also a strong chance that it will lose the NBA-champion Warriors to San Francisco by 2018, and the A’s play in a decaying baseball stadium in sharp contrast with my beloved Giants’ Insta-perfect AT&T Park.

Related: Record-Setting Baseball Fan Travels on a Minor League Budget

image

Lake Merritt is a popular outdoor spot in Oakland. (Courtesy: Visit Oakland)

Even when Lonely Planet ranked Oakland No. 8 on its “Best in the U.S. 2015” list, it inspired some snarky reactions. (Though this was partly guilt by association with such curious choices as Queens and Duluth.)

Inferiority issues aside, Oakland is getting great in its own way, and we need Oakland to be great—to capture some of the soul San Francisco has lost—for the good of the Bay Area, and attracting tourists is part of that. So when my friend Kim Bardakian, who works for Visit Oakland, offered to drive me around and show off the city she genuinely loves and lives in, I willingly played tourist for one Saturday.

image

The night ended by watching jazz star Arturo Sandoval at Yoshi’s. (Photo: Greg Keraghosian)

Not intentionally, that day was the Fourth of July. If anything, that kept Oakland from putting its best foot forward, because places that might swarm with visitors, such as Swans Market in Old Oakland, were closed. And in perfect symbolism, San Francisco had a fireworks show that night while you could only hear them across the bay in Oakland.

On the other hand, Oakland did have the weather advantage that day, as it often does: you couldn’t really see the fireworks in San Francisco either, because of Karl the Fog’s glorious arrival. And when I stepped out of Oakland’s BART station that morning, I realized I’d worn too heavy a shirt, forgetting it’s often 15 degrees warmer in the summer here.

10 a.m.

image

Outside Farley’s East, which makes a solid cup of coffee. (Photo: Greg Linhares/City of Oakland)

I was my typical grouchy morning self, so after Kim picked me up our first stop was in the Uptown district to get coffee at Farley’s East. For sheer depth of top-shelf caffeinating options, San Francisco has Oakland beat, but Farley’s delivers some excellent brew in a space that’s right out of a coffee snob’s design magazine, with a cute parklet outside comprising red tables and a wooden bench.

There is plenty to like about Uptown, and you could plan many fun nights here: I’ve seen my favorite all-time band, New Order, play at the Fox Theater, and it’s arguably the best music venue in the Bay Area. Make Westing is an unpretentious, beautifully dark cocktail bar with bocce ball where I would end this night, and although Pican serves Southern food at San Francisco prices, I’m still thinking about their fried chicken drizzled with honey truffle months after a visit earlier this year.

Uptown is also the focus of the monthly First Fridays and Art Murmur art walk, which includes food, live music, and gallery-hopping. I’d be remiss if I didn’t mention the dive bar Stork Club and its delightfully weird burlesque show that happens every First Friday (think of a stripper in a chicken suit).

Since my visit, Uptown has opened a new attraction: The Hive, an indoor-outdoor multi-use space with everything from restaurants to a brewery to writing workshops.

11 a.m.

If you’re going to wow a San Francisco snob, you should swing hard, so it’s no surprise that we started with the Grand Lake Farmers Market near Lake Merritt. Located near a freeway overpass, it doesn’t have the postcard appeal of the farmer’s market just across the bridge at San Francisco’s Ferry Building. But that also means it doesn’t have the swarms of tourists.

image
image

Scenes and produce from the Grand Lake Farmers Market. (Photos: Greg Keraghosian)

The market, which runs weekly on Saturdays, is a true local’s destination, and as I took my first walk around it, I was impressed by the high-quality goods and the friendly vibe. Any Oakland-phobe who deems the city too dangerous to visit has never been here – families and small children abounded as if we were in a suburban park.

As for the food, you could scam your way to a free meal just by strolling past all the free samples before splurging on some artisanal jam, organic produce, local grass-fed beef, or sustainably caught wild salmon. And if you’re not done gorging yourself, there are food trucks parked here too.

I explored the two main thoroughfares near Lake Merritt, which have evolved noticeably over the years. Grand Avenue is a work in progress, and it’s easy to see: next door to a run-down vacuum store is Alchemy, a beautifully appointed boutique liquor shop with an impressive array of whiskey, tequila, and other spirits.

image

What’s for sale at Alchemy, a boutique liquor shop on Grand Avenue. (Photo: Greg Keraghosian)

Noon

Oakland’s gentrification is front and center on Lakeshore Avenue, where we had brunch at Shakewell. It’s no accident I was taken here: the Mediterranean eatery was voted Best New Restaurant by Oakland Magazine this year, and it’s co-owned by two Top Chef alumni: Jen Biesty and Tim Nugent. With rustically appointed wood chairs and cedar banquettes, the place is stylish without trying hard, and the chefs are known to mingle with diners.

Mingling with me was Nugent, the pastry chef here who moved from San Francisco to Oakland several years ago. He spoke glowingly of the local culture and the support his venture has received from fellow Oaklanders – it’s not the only time I heard an Oakland restaurant owner speak positively about support that day, and it stuck with me because I’ve also heard overregulated San Francisco business owners complain of a lack thereof.

image

Shakewell’s looks and food have been a big hit in Oakland since it opened. (Photo: Courtesy Shakewell)

Shakewell’s tapas-oriented menu has been critically lauded for everything from its bombas to its croquetas with squid ink aioli. Maybe I just chose wrong, but I was underwhelmed by my brunch – the scrambled eggs were perfectly good, but the ceviche was dry for my taste.

1 p.m.

As we got back in the car and drove through such residential neighborhoods as Glenview, Oakland Hills, and Rockridge (the latter has become as expensive as San Francisco’s pricier ‘hoods), I asked my host, Kim, about her own reformation as a former San Francisco snob who never crossed the bridge. Now in her 14th year as an Oakland resident, she says she was won over by the city’s underdog factor, and its inclusiveness.

“There are no gay bars in Oakland,” she said, in contrast with San Francisco’s Castro neighborhood. “It’s just Oakland. There’s no sectioning off here.”

One other question did come to mind in the car: Oakland is bursting with top-notch restaurants, bars, and music, and a gritty sense of art and design that I wish we had in my Russian Hill ‘hood. But where are the artsy, modern boutique hotels San Francisco has in spades? How can the city be anything but a fun day trip from The City until it gets them? Kim acknowledged the hotel scarcity, and said the city is working to add them. One option coming soon to the East Bay is the 279-room Claremont Hotel in Berkeley, which was bought by the Fairmont and is expected to be fully renovated by year’s end.

image

Temescal Alley, which has turned from horse stables to hip row of boutiques. (Photo: Greg Keraghosian)

Next we parked in Temescal Alley, where the Brooklyn analogy does apply for once. It’s a hipster fantasy and the kind of place where I’d hang out: a converted horse stables turned into a narrow aisle of artisanal shops with ironing boards for tables. Old-timey barber shop? Check! Men’s clothing store with $300 slim-cut jeans made of raw Japanese denim? Double check, and man did I want some from Standard & Strange. Instead I chose a freshly baked doughnut from Doughnut Dolly, with the recommended Nasty Cream that is nasty good. You might also want to brave the long lines at Bakesale Betty’s, which opens for only three hours and is renowned for its fried chicken sandwich and chocolate chip shortbread.

Related: The Newest Hipster Neighborhoods Across the U.S.

image

Bakesale Betty’s patrons get to eat on ironing boards. (Photo: Greg Keraghosian)

3 p.m.

Whereas Temescal Alley is the kind of fashionable retail space that’s after my heart, I knew my snobbery would be tested at Jack London Square, the one part of Oakland you can actually call touristy. Except for the towering harbor cranes, the area does little for me aesthetically. A new addition here is a sprawling bowling alley/sports restaurant named Plank with service so bad my friends and I got concussions from beating our heads against the table to get a waiter’s attention during this year’s NFC conference championship game.

I will say this much for Jack London Square: it has a tiny bar by the water called Heinold’s First And Last Chance Saloon that dates to 1883 and is the rare tourist trap you want to be trapped in. On this Independence Day, the timeless interior full of relics was decked head to toe in red-white-and-blue bunting, which was only appropriate.

image

Fourth of July bunting joins the already eclectic walls at Heinold’s First And Last Chance Saloon. (Photo: Greg Keraghosian)

I will say this for Jack London Square as well: it has kayaking. And kayaking is always a good choice. I spent a relaxing hour rowing around the inner harbor, past yachts and house boats. I didn’t see seals up close the way I can by kayaking up north in Sausalito, and the view isn’t as majestic, but it does put me under the shadow of those massive cranes, which takes me back to my childhood thinking of the AT-AT walkers in Empire Strikes Back (even though George Lucas denied they inspired him). You can rent your kayak or paddleboard just a few feet away from the water at California Canoe & Kayak.

image

I go kayaking under Oakland’s cranes, with San Francisco’s skyline in the distance. (Photo: California Canoe & Kayak)

The lowlight of my day was probably having wine on the patio at Rosenblum Cellars, steps from the ferry terminal – not because of the scenery, which is excellent, or the wine, which was adequate. But I was baffled by the service, from simply trying to order a glass of wine instead of a tasting, to the tiered membership system, to the “serve-yourself” meat-and-cheese meals. Don’t make me feel even more inept than I already am, guys.

5 p.m.

But that led to the country music dinner that begins my story, and it showed me one way Oakland can be cooler than San Francisco: by not trying to be cool at all.

It was uptight hipsterism that helped inspire Paul Hayward to open Overland just six weeks before my visit. He told me about one night at San Francisco’s rocker dive bar Lucky 13, where dour locals were dissing any country singer that wasn’t on their short, pre-approved list. It made me think about our rocker beer garden Zeitgeist in the Mission and its own service-with-a-scowl attitude.

image

Dinner at Overland, including pulled pork sandwiches, onion rings, and frozen margaritas. (Photo: Greg Keraghosian)

So Hayward, who was wearing a black cowboy hat when I met him, aimed to create a fun, friendly country joint where Johnny Cash tunes could play right before Garth Brooks, where if you wanted cheap beer or whiskey you could order a Bud or Jack Daniels without being shamed. Where you could take a line-dancing class and look absolutely awful doing it as long as you smiled.

Somehow, the setup works. The menu is cheap and it satisfies, with stuffed burgers, Hank Style fries with pulled pork, and fried pickles. I washed down my meal with a $6 frozen margarita that comes in a jar, and I’d gladly order one again. I didn’t expect to walk out thinking it, but San Francisco needs a place like this. Because it needs to remember how it was before it grew up.

“The biggest thing I can say about Oakland, said Hayward, “is the palpable sense of energy. It reminds me a little bit of how San Francisco used to be.”

7:30 p.m. to midnight

image

Last call before the last train home at Make Westing, which has bocce ball. (Photo: Greg Keraghosian)

My friend Jeremy and I finished the night by taking in a concert at Yoshi’s, a jazz venue/sushi restaurant in Jack London Square that’s been drawing big acts for over 40 years. I know little about jazz, but on this night we got Arturo Sandoval, who Jeremy says is a big deal, and as chill music venues go, Yoshi’s is great.

We finished the night with drinks at Make Westing and I ducked into BART before my train turned into a pumpkin at midnight. It’s been over two months since my visit and I haven’t been back to Oakland – old habits die hard. But for the first time I’m getting some Oakland FOMO when I don’t go, and I guess that’s a start.

WATCH: Hospitality or Hazing? Surviving a Vodka Fueled Night in Mongolia

Let Yahoo Travel inspire you every day. Hang out with us on Facebook, Twitter, Instagram, and Pinterest. Check out our original adventure travel series, “A Broad Abroad.”

For more on Yahoo Travel’s travel policy, click here.