Welcome to Leafly’s travel series, our definitive cannabis-infused guides to the best cities in the world.
Oakland, California is one of the most vibrant, diverse, and culturally rich cities in America. Often overshadowed by its sparkly sister across the Bay, Oakland offers a kind of cultural freedom, pugnacious spirit, and economic diversity that San Francisco long ago lost. The weird, the hip, the punk, the blue collar, the quirky, the hard-working, the straight, the queer—all are welcome in The Town. And as Oakland solidifies its place at the cutting edge of the California cannabis movement, cannabis enthusiasts of all stripes are warmly welcomed here, too.
Cannabis legality: Medical (18+, med card and ID required)
Nicknames: Oaktown, The Town, Bump City
Claims to fame: Jack London, Angela Davis, The Raiders, Green Day, Steph Curry
For the record: Oakland has more artists per capita than any city in the nation.
At 4:20 p.m., you are: Ordering an Uber X after checking into your room at the Inn at Temescal, a newly redone hipster motel in the city’s up-and-coming Temescal district. Point your driver to 1840 Embarcadero, home to Harborside Health Center, California’s most iconic medical marijuana dispensary. Founded by MMJ pioneer Steve DeAngelo, Harborside remains the gold standard for dispensaries nationwide. Some flower strains sell out, but they’re followed by others that hit the dispensary floor soon after they’re purchased from local farmers. The selection is wide – edibles, concentrates, dozens of flower strains – so you’ll have no trouble finding plenty to purchase.
Head's up: California is a medical state, not recreational. So if you want to get past the door at Harborside Health, you’ll need a California med card. (You will get carded.) Also, Harborside can be tricky to find, so don’t exit the Uber until you lock eyes on the “1840 Embarcadero” sign. Trust me. You’ll need a cab or Uber to get back downtown, too.
At 5:40 p.m., you are: Getting your game face on at Beast Mode, the athletic apparel boutique owned by former Seattle Seahawk running back Marshawn Lynch. Oakland born and raised, Lynch is a proud local booster, and his store is a great place to kick off a walking tour of downtown.
At 6:00 p.m., you: Start walking north up Telegraph Avenue. Starting at 12th and Broadway, serpentine your way up to the Fox Theatre at 19th and Telegraph. If you’ve timed it right, you’re entering Oakland’s arts district on the first Friday of the month, when Oakland Art Murmur goes off. Take a few hits of a pre-roll or vape, then pop into local galleries that cluster near the Broadway and Telegraph, like Betti Ono, Oakstop, Joyce Gordon Gallery, and Pro Arts. Keep your eyes out for storefronts that host art happenings on First Friday, like SoleSpace: by day a sneaker boutique with sweet red Pumas, by night a hot cultural venue with local musicians and poets.
At 7:25 p.m., you’re: Scanning the menu at Rudy’s Can’t Fail Cafe, the bustling joint named for the Clash song and co-owned by Green Day bass player Mike Dirnt. We recommend the chupacabra burger. End your meal with a cup of hot black from Oakland Coffee Works, the sustainable bean company recently founded by Dirnt and bandmate Billie Joe.
At 8:45 p.m., you’re: Rolling a bocce ball at Make Westing, a cocktail bar across the street from Rudy’s. Voted Oakland’s friendliest bar and “best place to meet members of the opposite sex,” Make Westing features two full-length indoor bocce courts and a bar menu that runs from cheap tallboys to craft cocktails.
At 9:25 p.m., you’re: Climbing the stairs to Feelmore Adult Gallery, a progressive sex-positive boutique run by Neena, a local businesswoman who put up a courageous fight to get her store permitted in famously liberal Oakland. (Check out the story here.) Neena will dialogue with you about kindness, safe words, and respect, or she’ll leave you alone to browse; your choice. She’s open until midnight on Fridays.
At 10:05 p.m., you’re: Hanging in one of two bars. First: Jack London frequented Heinold’s First And Last Chance Saloon, the city’s oldest watering hole, and the place still has a slanted floor, which happened when the pilings beneath shifted during the 1906 earthquake. Second: The White Horse is America’s oldest continuously operating LGBT bar, and today it’s full of EDM parties, karaoke nights, queer comedy, and general fun-having.
At 10:05 a.m., you’re: Strolling seven blocks from the Inn at Temescal, south on Telegraph Ave, to pick up a few extra supplies at Telegraph Health Center. We recommend the Gold Drop medicated honey. Go easy, though.
At 10:30 a.m., you’re: Deciding between Popeye eggs or the Liège waffle (so divine it wants neither butter nor syrup) at Blue Bottle Coffee, the Oakland-born boutique coffee house. There are ten Blue Bottle locations in the Bay Area, but we recommend the one in Oakland’s historic W.C. Morse building. High ceilings, enormous windows, and a chatty clientele give this place the feel of a bustling European plaza. For entertainment, watch the mechanics work over espresso machines in the shop behind the seating area. Don’t miss Blue Bottle’s New Orleans-style iced coffee, a sweet and shockingly delicious energy jolt.
Word to the wise: Blue Bottle hosts free public coffee tastings at its Webster Street roastery every Sunday at 11:30 a.m. and 3:00 p.m., and a “How to Brew” series Sundays at 1:00 p.m.
At 11:30 a.m., you’re: Rifling the racks of Roxy Music, Screaming Trees, and classic DEVO LPs at 1-2-3-4-Go Records, Oakland’s coolest vinyl shop. The classic stock turns over constantly, and limited-edition releases by rising local bands show up here first. Shoot some old-school selfies in the in-store photo booth and discover new grooves at the listening station in the back room. Look for live performances on weekends and some weekday evenings. Don’t miss the sidewalk library next door, a public micro-plaza stocked with yesterday’s freshest newspapers and magazines.
At 1:00 p.m., you’re: Digging the sculpture garden at the Oakland Museum of California, one of the Bay Area’s can’t-miss art stops. The garden includes Tony Labat’s Big Peace IV, a massive canary-yellow steel peace sign, and our fave, John Mason’s Yellow Cross Form, which the years have turned yellow-green so it now looks like a massive 3-D dispensary sign. The museum currently features “Altered State: Marijuana in California,” the first-ever museum exhibition to focus on cannabis in the Golden State, on view through September 25, so see it before it leaves.
What you’re skipping: An Oakland A’s game at the O.Co Coliseum, major league baseball’s most notoriously shoddy ballpark.
At 3:20 p.m., you’re: Lying in a grove of redwoods at Redwood Regional Park, which actually lies within the city limits of Oakland. These aren’t the old growth ancients with rings older than Columbus – those you’ll find 300 miles north in Redwood National Park. The redwoods here are second growth, raised up after ye olde pioneers sawed down the originals. But they’re still impressive, organic skyscrapers that are really cool to stand or lie under and gaze skyward (especially when medicated, though we recommend consuming before you reach the park in the interest of being respectful to others). Take a moment to touch the tree’s soft, thick bark, which feels like furry leather.
Head's up: While it’s technically in the city, the state park does take a few minutes to reach by vehicle. Uber or a cab will get you there, as will the AC Transit #39 or #339 from the Fruitvale BART Station.
At 4:20 p.m., you’re: Leaving town via public transit and heading to the airport or your next destination, wherever that may be. BART is the best way to get from Oakland to San Francisco or SFO – and from there, the world is your oyster.
Image Sources: Inn at Temescal, Betti Ono, Rudy's Can't Fail, and Blue Bottle Coffee via Facebook, Beast Mode via Instagram, Make Westing, Calibas via Wikimedia Commons, Bruce Barcott, Oakland Museum of California, and Michael McAreavy and Ed McGowen via Flickr Creative Commons