1 City, 3 Ways: Oakland

While San Francisco might be the heart of the Bay Area, Oakland is definitely its soul. Sunny, with easy transit and a strong restaurant game, Oakland is–as Oaklanders will tell you–ON. In the time it takes to walk up and down Lombard Street in SF, you can zip across to the sunny side of the Bay (aka Oaktown, if you’re a local). Here, we’ve put together a bunch of Oakland’s “greatest hits” into three different itineraries.

Nibble and Stroll

Start your morning at the Ferry Building in San Francisco, where you can grab coffee and a flaky pastry at Oakland-roasted Blue Bottle Coffee. From here, take the ferry to Jack London Square. Views of the Bay Bridge are amazing as the ferry passes underneath. Stroll through the Square, then Uber over to one of Oakland’s oldest and most diverse neighborhoods, Grand Lake.

Blue Bottle’s coffee is poured one cup at a time. (Photo credit: Blue Bottle Coffee/Melissa Ryan)

If you’re there on a Saturday, shop and sample your way through the Grand Lake Farmer’s Market (9 am – 2 pm), where you’ll find seasonal fruit, baked goods, meats, cheeses, sweets and more. If you’re adventuring Tuesday–Sunday, stop in at the original/flagship location of  Arizmendi, a worker-owned cooperative bakery.  Make sure to try the fresh-out-of-the-oven breads or the gourmet pizza of the day.

Next stop: Lake Merritt. Known as the “jewel of Oakland,” the Lake is a trendy gathering spot, and the 3.4-mile path along the water’s edge has a block party vibe on weekends. Loop the entire lake in one go, or stop and spend time exploring along the way–you’ll find gondolas, the oldest wildlife refuge (1870!) in the United States, and the Lake Chalet, a renovated boathouse restaurant over the water.

End your day at city fave Homeroom–they’ve got 13 different varieties of mac-n-cheese, or  you can customize your own. Don’t leave without trying the homemade Oreo cookie.

A bite + a bite + a bite….we’ll try them all, please. (Photo credit: @Homeroom510/Reese Lichtenstein)

Like A Local

Make your way to the Temescal neighborhood, filled with artist’s spaces, independent shops, and destination restaurants. Visit Temescal Alley for fresh doughnuts and coffee at Doughnut Dolly, find a new favorite statement necklace at Marisa Mason and then walk around the corner to Bakesale Betty to pick up a picnic lunch (locals line up daily for the addictive fried chicken sandwich). Spend a dollar to join the rest of the neighborhood at the Wine Mine’s weekly wine tastings , then buy your favorite bottle to complete your picnic.

The beachy-meets-luxe style of Marisa Mason’s handmade pieces. (Photo credit: @marisamasonjewelry)

A 15-minute drive to Alameda Beach will reward you with one of the best SF views you’ll see. Bonus: there are no tourists in sight–it’s a local secret. Definitely dress in layers, as Bay Area weather is notoriously fickle.

If you’re in the mood for something sweet after the surf, swing by Fenton’s, Oakland’s beloved ice cream parlor, open since 1894. The Black and Tan sundae is the one to get.

For a neighborhood-style dinner, go to Dona Tomas, Boot and Shoe Service or Pizzaolo, and for a true Oakland-style end to your evening, sit at the bar for a beer at the Kingfish Pub and Café–possibly the best dive bar ever.

Active Adventure

Hudson Bay Café, a local hangout in the heart of upscale Rockridge, is the perfect place to begin this adventure. Fuel up on strong coffee, then amble around the neighborhood to window shop and browse.  Try Atomic Garden for souvenirs and gifts, Body Time for custom-scented cosmetics, and Bittersweet for chocolate delights.

If it’s Sunday, follow the crowd to the Rockridge Farmer’s Market, where you can stock up on picnic supplies. Any other day of the week, go to Market Hall, which is an epicure’s delight. If you’d rather stay in the neighborhood and people watch, try Southie, where it’s all about the Spicy Hog, or Ike’s Place.

Drive to Inspiration Point in Tilden to enjoy your picnic and a walk along the Nimitz trail for stunning views of the Golden Gate Bridge and San Francisco.

If it’s Friday, you’re in luck – you can go to the Oakland Museum for their festive night market, with Off The Grid food trucks, half-price museum admission, live music, and more. If it’s the first Friday of the month, you’re even luckier – you can join everyone for the Oakland First Friday, an immersive art experience. Walk through the streets, celebrate art, and enjoy drinks, food, and music.

Oakland’s Lake Merritt lights up for nighttime strolling.

Still going? For a night of dancing to funk, hip-hop and reggae, city-wide favorite Layover is the place you want to be. Don’t be surprised if you get invited to a few friendly dance-offs.

– Kendra Collins