Oakland, California, is a melting pot of cultures, with a creative spirit that invites just about anyone to feel at home. Adventurers will enjoy the hiking trails in the Oakland Hills, while artists and musicians can spend hours perusing the local art galleries, music venues and street art that define Oaktown, or “The Town,” as the locals call Oakland. (Fun fact: They also refer to nearby San Francisco as “The City.”) Plus, there’s a diverse mix of restaurants where foodies can sample everything from Burmese food to tapas.
There’s a reason why the city’s tradition of civic pride is still very much alive — its blend of generations-old families and a new era of artists and techies create a spirited energy that’s hard to replicate anywhere else. To experience the best of all of Oakland’s angles, follow this three-day itinerary that will immerse you in delicious dining, piles of culture and more.
As always, check for travel guidelines and closures before planning your trip.
Friday: Hike, Shop and Dance Your Way Through Oaktown’s Hot Spots
You can’t visit NorCal without a hike amid some redwood trees. The closest option to downtown is the Dimond Canyon trail system in the Oakland Hills. Grab some pastries at the worker-owned Arizmendi Lakeshore, which specializes in scratch-made pastries, bread and sourdough pizza, to fuel up before starting your nature exploration at the Dimond Canyon Bridgeview trailhead on Monterey Boulevard. Here you’ll find locals doing trail runs, as well as friendly trolls — yes, creatively placed troll sculptures — welcoming you along the meandering path under towering redwoods.
Once you’ve worked up an appetite, venture over to one of Oakland’s favorite shopping districts, Temescal, and grab a table at Burma Superstar. This Oakland outpost of a San Francisco favorite has a cult following in its own right — the rainbow or tea-leaf salads are must-tries.
Spend the afternoon exploring the Temescal Alleys, a pedestrian shopping area located off 49th Street. Some of Oakland’s most unique artisanal shops call these alleys home, and visitors can find everything from carefully curated jewelry at Esqueleto to rare indoor plants at Crimson Horticultural Rarities.
If you happen to be in Oakland on the first Friday of the month, make your way south on Telegraph Avenue to experience the biggest block party in town. This monthly event, fittingly called First Fridays, sets up shop between 22nd and 27th streets and hosts artists, musicians and food trucks for an only-in-Oakland experience.
Just getting the night started? Indulge in the craft beer scene at Drake’s Dealership, a hip outdoor beer garden that serves up delicious pizza, before heading out for some live music at the Fox Theater in the Uptown neighborhood. This historic venue hosts big-name artists every day of the week, but if you’re seeking something a bit more intimate, head to the New Parish, which highlights local music.
Saturday: Indulge in Serious Eats While Exploring Lake Merritt
Start the day off with breakfast at Lynn & Lu’s Escapade Cafe, where the menu has all of the start-your-day classics like eggs Benedict and pancakes topped with whipped cream. Don’t forget to make a quick stop at Oaktown Spice Shop to check out some seriously unique spice blends before heading across the street to the Grand Lake Farmers Market, a locals’ haven for all things fresh, featuring more than 40 vendors.
Take a stroll along the south side of Lake Merritt and make your way into Chinatown for lunch at Shandong Restaurant, which serves up arguably the best dumplings and noodle dishes in town.
If you have young kids in tow, visit Children’s Fairyland along the north side of the lake. One of the earliest theme parks in the U.S., this storybook-themed amusement park touts the oldest continuously operating puppet show in the country. If you’d rather take a break from the outdoors, catch a movie at the historic Grand Lake Theatre.
For dinner, you can’t go wrong with Shakewell, a Mediterranean tapas restaurant that serves a seasonal menu in a hip setting. End the night with a drink at the Alley Piano Bar & Restaurant, one of the city’s last remaining piano bars, where locals are not afraid to belt out everything from show tunes to contemporary hits. Founded in 1934, this Oakland institution seems to be frozen in time — as evidenced by the 50,000 or so business cards that visitors have stapled to the interior over the years.
Sunday: Take In the City’s Art and Wine Scenes
Sunday brunch is a way of life in Oakland, and one of the best spots in town is Portal, with its famous beer garden overlooking the south side of Lake Merritt. The chicken and waffles are always a hit, but it’s also difficult to pass up an order of garbage bread, their housemade strombolis.
Next, head to the Oakland Museum of California for a morning of California art, history and natural science exhibits. This spot is a true representation of the Oakland community, hosting weekly events and rotating exhibits that explore everything from Burning Man to the Black Panther Party.
For more art, walk over to the Old Oakland historic district, the “original” downtown, to check out local creativity on display at E14 Gallery or the Artists Loft (by appointment). After your morning’s exploration, a quick bite at Ratto’s International Market & Deli, a fourth-generation Italian deli, will be just what you need for lunch. (Grab a classic Italian sub; you won’t be disappointed.)
Next up: Head to Jack London Square, situated along the San Francisco Bay and named after the famous author who used to spend his days here. You’ll be greeted by boats docked in the marina and a ferry building that runs daily ferries to San Francisco.
This part of town is also known for its urban wineries, like Rosenblum Cellars and Brooklyn West Winery, as well as several breweries along the Oakland Ale Trail — all of which offer tastings. Looking for something a bit more family-friendly? Plank is the ultimate family playground, with bowling, arcade games, bocce and a beer garden.
Nearby dinner options include Farmhouse Kitchen Thai Cuisine, serving “new generation” Thai food that focuses on spice, and the Forge for wood-fired pizza. If you’re craving Mexican food, make your way to Nido’s Backyard for its colorful backyard-patio vibe and a quesabirria — a quesadilla filled with beef birria.
Then grab a drink at Heinold’s: First and Last Chance Saloon, which is not only an original Jack London hangout from the early 1900s, but still touts a slanted floor that was the result of the 1906 San Francisco earthquake. Of course, if you like jazz (and/or Japanese cuisine), nearby Yoshi’s should be your last stop of the day. It’s a local favorite for live music, and the perfect place to wrap up your weekend in Oakland.
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