It’s been called “San Francisco’s Brooklyn,” and San Francisco’s sister city, just across the water in the East Bay region, has the same kind of historic twists, beautiful views, and exploding food and wine scene as that New York borough. Diverse, dynamic, artsy, edgy—Oakland invites you to add a colorful twist to your Bay Area adventures. An influx of young locals, drawn not only by the vibe but by the city’s lower rents too, have moved into downtown lofts and condos, and so have come the single-pour coffee bars, cafes, galleries, and clubs, too. Lower costs in the East Bay have also lured chefs—both established big names and new-gen kitchen whiz kids—to open restaurants here, in settings ranging from splashy Art Deco (Flora) to sleek hipster chic (Plum).
Jack London Square, an inviting complex perched on the edge of San Francisco Bay, mixes outdoor fun with indoor diversions. The square is named after the intrepid adventurer and author of Call of the Wild and The Sea Wolf, a book allegedly inspired by tall tales told by the crusty folk who frequented the legendary—and still open—Heinhold’s First and Last Chance Saloon. Near the sloped entrance to the historic watering hole, the wall hands on the wall clock haven’t budged since April 18, 1906—the moment a massive quake struck the Bay Area, and jolted the building so much the timepiece stopped ticking. Time may have stopped, but not service, and stepping down into this little wooden shack is about as time-warpy as you can get: 19th-century gas lamps glow each evening, World War II photos photographs and memorabilia, and a small photo of a young London sitting at one of the saloon’s tables adorn the walls. Settle in and talk to your elbow-mate at the bar; you never know what tall tales you might hear.
But save your visit to this historic bar until later in the day. When the sun’s up and shining, paddle a kayak around the adjacent Oakland Estuary, especially lively during the fall bird migration. You’ll also get great views of the oddly creature-like dock cranes used to load cargo ships. Urban legend says the cranes inspired local filmmaker George Lucas to create the ominous AT-AT Walkers in Star Wars; true or not, the cranes do resemble the movie’s creepy four-legged tanks.
Post paddle, stroll the square to visit shops, or tour two historic vessels: the Lightship Relief, a floating lighthouse which aided navigation along various U.S. coastlines from 1951 to 1974, and the USS Potomac, President Franklin Delano Roosevelt’s historic yacht (ask about bay cruises). Dine at inviting options like Baia for organic pasta, or have crab cake benedict for brunch at Oakland Grill. Farmers’ markets and outdoor movies add to Jack London Square’s neighborhood-y appeal.
The warehouse-filled back streets of the East Bay are attracting urban wine warriors who like blending and bottling in the middle of city buzz. More than 20 wineries dot Oakland and the nearby cities of Berkeley, Emeryville, and Alameda; visit them on your own, or consider taking an entertaining guided tour by bike with East Bay Winery Bike Tours.
Oakland and surrounding cities are also enjoying a culinary renaissance as celebrated chefs open new establishments in up-and-coming neighbourhoods such as Uptown, Jack London Square, Grand Avenue, and Glenview. Try sophisticated tapas at always-packed Bocanova, contemporary Japanese at Ozumo, or charcuterie and craft cocktails at Adesso. Chicken and waffle fans flock to West Oakland’s Brown Sugar Kitchen, where chef Tanya Holland puts her creative twist on classic soul food dishes.
Oakland is becoming a hotbed of artisanal food makers too, with getting-to-be-household names like Numi Teas, Blue Bottle Coffee and Linden Street Brewers making the region home base for operations. Learn more about this new wave on a guided walking tour with Savor Oakland, focusing on food, culture, and history. Wind down the evening and recline in Kasbah-like splendour at Layover.
With vibrant galleries, hands-on activities, education programs, and community events that celebrate and illuminate California—past, present, and even future—this museum is an exciting cultural hub near Oakland’s Lake Merritt. Established in 1969 as a “museum for the people,” OMCA brings together collections of art, history, and natural science, all wrapped with beautiful terraced gardens.
Time your visit for a Friday and your experience gets even better. Friday Nights @ OMCA are family-friendly outdoor parties, with live music, spontaneous dancing, gourmet food trucks, and local craft beer and wine at the Blue Oak beer garden. Get creative at drop-in art workshops and learn from locals in the Makers & Tasters Series.
With elaborate peaks, turrets, and moldings of classic Victorian-era buildings, this is one of Oakland’s prettiest districts. Historically, it’s where locals used to put on their finery and strut; today, it’s an eclectic mix of businesses, indie shops, and restaurants, and its roughly six block area of richly restored buildings makes a delightful place to stroll and explore. See handcrafted furniture at SOBU. Browse for good reads at Bookmark, an independent non-profit used bookstore. Mix with locals at weekly board game nights at EndGame (bring your own or use theirs). Swan’s Market, a longtime neighborhood hub, is morphing into a food hall, with Mexican dishes at Cosecha, wine tasting at Periscope Cellars, and sausages and beer at Rosamunde’s. On Friday mornings, check out the scene (as well as fresh produce and artisanal foods) at the bustling farmers’ market on Ninth Street between Broadway and Clay. At night, old-fashioned streetlights cast a warm glow, with restaurants like Desco and The Trappist tempting you to come in, relax, and enjoy a good meal.
The artistic spirit thrives in Oakland. One of the best—and most unique—ways to experience the city’s artsy side is to take part in the monthly Oakland Art Murmur event called First Friday. On the first Friday of each month, member galleries on Telegraph Avenue between Grand Avenue and 27th Street put on one heck of a street party. Pop-up and permanent galleries in industrial workshops let you browse and buy extraordinary art—and chat with the artists. Food trucks selling almost any kind of fare, super-excited little ones dancing to DJ music, beer gardens, street performers—First Fridays are a kaleidoscope of colors, cultures, and lifestyles.
For a calmer way to tap into the art scene, join a weekly Saturday Stroll, with galleries and mixed-use venues welcoming visitors from 1 pm to 5 pm. Many galleries also host free cultural programs such as receptions, artist talks, lectures, musical performances, and literary readings. Oakland Art Murmur also offers monthly, guided walking tours (third Saturday of each month), when a gallery director or other prominent member of the Oakland art community takes visitors to 3-5 galleries for presentations from curators or artists. If you really want to get hands on, visit The Crucible. Classes and workshops teach ceramics, stone cutting, jewelry making, and a host of other art forms.
Need something to do? Oakland’s event calendar is packed with a wide array of ways to learn and experience the character of this dynamic city, first hand. In summer, take part in Art + Soul Oakland, with live music and dance parties, barbecue face-offs, poetry slams, and an eclectic, multicultural artisan marketplace.
September’s Eat Real Fest feels like a state fair in the streets—an urban celebration that aims to help people understand where their food comes from, and who grew, raised, or made it. It’s all about delicious, regionally sourced, sustainably grown foods, and you’ll find plenty of ways to eat and learn about the ultra-fresh food showcased here.
Oakland also offers cultural events throughout the year, including performances by the Oakland Ballet and Oakland East Bay Symphony, at the Paramount Theatre, an Art Deco masterpiece in downtown Oakland (guided tours, the first and third Saturdays of the month, are well worth it).
In 1883, people in the East Bay got their first chance to see the sky in a whole new way. That’s when this facility, then called the Oakland Observatory, opened its doors, inviting the public to head up through the redwood forests cloaking the Oakland Hills to peer through a powerful telescope pointed at stars, planets, and distant galaxies. Today, Chabot Space & Science Center is the largest public telescope facility in the country, with three powerful telescopes, a digital planetarium, and a large screen theater. It’s not just about looking up here—there’s also hands-on science center (great for kids into science and exploring) with ways to learn about cutting-edge discoveries, including solar-powered cars and what it’s like to be on a mission to Mars.
Temescal is Oakland’s hipster hangout, and if it’s trendy, tasty, or on topic, it’s here. This leafy corridor of gentrified buildings lining Telegraph Avenue is an appealing hub, especially on sunny weekends when with lots stroller-rolling families and 20-something weekend brunchers are everywhere. If you want to graze like a local, get in line at Bakesale Betty to try a Fried Chicken Sandwich, or have a gooey-perfect Grilled Cheese Trinity sandwich at Sacred Wheel Cheese Shop. For a sophisticated sip, visit Hog’s Apothecary, where a certified cicerone (beer sommelier) will help you pick from 25 hand-selected, brewery-direct beers on tap daily. If you have little ones in tow, let them scramble and play at Frog Park, a former vacant lot transformed by 1,300 volunteers into an ultimate playground, with climbing structures, safe swings, and splashable Temescal Creek.
For a delicious exploration, sign up for an Edible Excursions guided walking tour, which includes tastes of local finds such as gourmet doughnuts, Ethiopian spreads, fresh-roasted coffee, Indian street food, Baja-style fish tacos, and Korean tofu stew. Also fun: $1 wine tastings on Saturday afternoons at The Wine Mine.
When it comes to cities, adding water can be a good thing—a visual break from the urban glass, steel, and stone. So it goes with this sparkling jewel. Fed by the adjacent Oakland Estuary, saltwater Lake Merritt is a popular spot, and the 3.5-mile/5.6-km path that circles the lake is always filled with locals jogging before work, stretching their legs at lunchtime, or watching the lakes “necklace of lights”—more than 4,000 lightbulbs on 126 lampposts—blink on at the end of the day.
Lake Merritt also holds the distinction of being designated, in 1870, as America’s very first National Wildlife Refuge, and it still provides important habitat, particularly for migratory birds in fall. Rent a canoe, kayak, or pedal boat at the Lake Merritt Boating Center, in the historic Lake Merritt Sail Boat House, and keep your own bird count—or check out what you think you saw at the lake’s Rotary Nature Center. Other diversions include the 1876 Camron-Stanford House, a stunning example of the regal Victorian homes that once lined the lake, and the bonsai collection at Lakeside Park Garden Center. After all that fresh air, head indoors for a first-run movie at the lavish 1926 Grand Lake Theater (Friday and Saturday shows in the main auditorium include a concert on the theater’s Wurlitzer organ).
End your road trip by exploring one of the world’s great cities. Famous for grand-dame Victorians, classic cable cars, dynamic diversity, a beautiful waterfront, and a soaring crimson bridge, the “City by the Bay” truly has it all. Trend-defining cuisine ranging from Michelin-starred dining to...