Uptown, one of the greatest neighborhoods in the country, is a sliver of Oakland with a thriving beat. The diamond-shaped district of Uptown is the area bordered by 27th St and 14th St to the north and south, San Pablo/980 to the west, and Harrison Street to the east, with Telegraph Avenue and Broadway being the two main lifelines of the neighborhood.
An art deco-era hub of entertainment during the 1920s and beyond, the area slowly fell into disrepair after WWII. Lack of industry left empty buildings and brought a growth in crime, but Oakland’s center began to revitalize during Mayor Jerry Brown’s 1999-2007 term and initiatives to increase business and housing. Change came, as did gentrification, causing affordability concerns along with growth.
Now uptown is on the verge of another major change. Uber’s headquarters are slated to open in fall of 2017 with Fortune.com estimating the move to bring 2,000 - 3,000 new jobs. Uber will settle in the iconic H.C. Chapwell Company building which opened in 1929 and housed Sears from 1996-2014. In the last decade, uptown has really boomed with nightlife heralded by the reopening of The Fox, public art efforts, increased housing, and basically tons of cool stuff. On weekend nights, the corner of 18th and Telegraph is buzzing with a diverse crowd and electric energy.
Once the weather warms again, take a free walking tour to learn more about architecture, history, and juicy stories of Oakland. In the meantime, you can explore the new, vibrant Oakland through all the amazing places to eat, drink, and enjoy art all in a few square blocks.
468 19th Street
This contemporary Spanish restaurant is your first stop after hopping off at 19th Street BART. Wood chevron parquet floors, beautiful custom barstools and tables, and a soaring ceiling with an intimate vibe welcome you in. Before a night on the prowl, share tapas like the bunuelos de queso (aka gruyere fritters) over a glass of wine or one of their extensive sherry selections. For more sustenance, seek out the fideu caldosa -- crispy rice-like noodles served in pan with chicken, shrimp, and savory spices. There’s easy seating regardless of reservations, and duende means the spirit of passion in Spanish -- so this is the perfect spot for a spirited night on the town.
Just kissing Uptown’s north end you’ll find the Sweet Bar. This airy, counter-service cafe has large windows overlooking Broadway and pumpkin ginger cupcakes that’ll make you weep. Owner Mani Niall sources all things local, organic, and delicious for his sweet and savory menus. His pot pie turnovers, housemade focaccia bread sandwiches, sour cream cheesecake, rich espresso drinks, and house macaroons will have you coming back again and again. And they have lots of gluten free goodies, too.
2270 Telegraph Avenue
Vibrant, irie, delicious—this restaurant and rum bar is the perfect start to your Uptown night. Owner and Chef Nigel Jones was raised in Kingston, Jamaica and blends the flavors and feel of the island with Oakland’s fresh, local vibe for truly delicious dishes. Standouts include their spicy, organic Jerk Chicken that’s been marinated and smoked for hours for a taste so tender and spicy, you’ll want to dance. For the more adventurous palates, try the rich and delicious curry goat. They also do a delicious Sunday brunch.
37 Grand Avenue
This Uptown wonderland is perfect for rainy days with a book, looking effortlessly cool on first dates, and craft cocktail-fueled gossip hour with friends. There’s no phone or website for this bar/restaurant, so you’re just gonna have to go visit. Small Wonder is open “7am - ish” until 11 pm or so each day. The owners once did small theater and their skill in creation and design shines through the space; the former print shop has been transformed into a lush, plant-filled, mural covered, vintage furniture littered, record playing, colorful delight of an oasis. Even the communal bathroom sink is exciting. Have delicious comfort food like the open face roast chicken sammy with pan gravy and cranberry, sip their tasty coffee, indulge in fancy cocktails, and share small plates.
1644 Telegraph Avenue
Fun and friendly—Dogwood has all the attributes of a great first date bar. It’s not-stuffy-fancy, with a curated craft cocktail featuring classics and house creations alike. Gourmet grilled cheese (made on a griddle in the bar’s seating area)with add-ons like whiskey bacon chutney will fuel you for the night, or share the charcuterie plate to dazzle your date. The exposed brick wall, warm wood tables, and neon sign outside make this an uptown must. If you’re feeling frisky, step through the adjoining door to sister bar, Darling’s Elixirs. Inside the former pharmacy, order up your medicine at the vintage prescription counter and start feeling better immediately.
2272 Telegraph Avenue
If you prefer a touch of dive in your Uptown experience, you best stop by the Legionnaire. The two-story pub is your one-stop shop for dancing, drinking, sports-watching, and general skullduggery. Rarely a cover (unless there’s naked folk getting burlesque-y upstairs), you can find a dance party most days of the week. Highlights include Wednesday’s Strictly Business hip-hop parties and Motown Mondays -- we bet that whatever else you might do on a Monday night doesn’t include its own hashtag (#MoMoak). Extra double bonus points for a record playing jukebox and pinball machines.
Tucked inside The Hive’s multi-use space Uptown, Drakes Dealership is your go-to spot for craft beer, woodfired pizza, and one of the best dog-friendly patios this side of heaven. Drake’s Brewing Co. was at the forefront of the Northern California microbrew movement, opening their San Leandro brewery in 1989. Now you get decades of brewing excellence in this hip, exposed brick, firepit-having, centrally located hangout. Play around with the Imperial IPA Denogginizer and find out why they’re one of the East Bay’s best breweries. Oh, and did we mention the live music?
1807 Telegraph Ave
The gorgeous Fox Oakland marquee heralds your arrival in the heart of Uptown. Originally opened in 1928, the lavish Art Deco movie theater soared for 40 years, until it fell into disrepair and sporadic use. The last decade saw community and city cooperation to restore its former glory, and since reopening in 2009, it’s been pulling in world-class acts year-round. From the decadent interior to the cushy theater seating -- and none of the hassle of getting to SF -- you’ll be in music heaven with everyone from John Prine to Snoop Dogg.
474 24th St
Movie theater, restaurant, beer joint, couches, lounge chairs -- the New Parkway kinda has it all. See a wide range of flicks, cartoons, classics, and documentaries for $8 (or pay-what-you-wish during Karma Cinema Wednesdays). In addition to movies on comfy couches, there’s trivia night, drink & draw events, open mic and stand-up comedy, popcorn poker, bingo, and beer -- honestly, you may never leave. All the libations are locally sourced within 200 miles, so you can drink with integrity. And, there's real butter on the popcorn.
1928 Telegraph Ave
The Uptown’s a great joint, with its cavernous interior lying in wait for your shenanigans below its glowing blue sign. Have a cocktail in the main bar at the entrance, discover what party/comedy show/dance performance is live that night in the big room, or slip out back to the mural-covered back patio for a flirty moment under the city stars. There’s a Hella Gay dance party every third Saturday, and the monthly calendar has everything from thrasher metal shows to burlesque babes baring it (mostly) all.
300 Lakeside Dr
Step out of the streets and up into the sunshine on this three-acre sky-high park. The garden atop the Kaiser Building is serene, with reflecting pools, a walking bridge, trees, birdlife, even a free concert series on Fridays at noon during the summer. You could hang out there all the time and just call it your new full-time job. Open since 1960, the roof garden set a precedent for others to come (we’re looking at you, SF POPOS); gain access to this urban oasis by pushing the RG button (roof garden, darling) in any Kaiser garage elevator. It’s open to the public from 8am-6pm, Monday to Friday.
1703 Telegraph Ave
You’re an adult. As such, you belong in an adult gallery. This tiny shop, open until 9pm on weeknights and midnight on weekends, is an excellent place to pop in when cruising Uptown. The sex-positive, body-positive, welcoming space has every gift you might ever need give. The educated folks of Feelmore offer workshops about sex and also provide community space for weekly events like comedy night (Right?! Sex is funny.) and erotic readings. Stop in, say hi, and buy a toy.
Various locations Uptown
Get your Uptown Oakland art fix in three, free easy ways. 1) Take a (free) guided art tour from 2pm-4pm on the third Saturday of each month. Hosted by Oakland Art Murmur and led by rotating curators and artists, the tour will take you to three to five Uptown galleries based on monthly themes such as Art and Irony, Revolution, or Contemporary Art in the Bay Area. 2) If tours make you cranky, opt for the weekly Saturday Stroll, with participating galleries open from 1pm-5pm. 3) If you’re more rocker than quiet artist, join the throngs for Oakland First Fridays, when a street party/art walk/live music/food truck/maker faire extravaganza takes over five blocks of Telegraph from 5pm-9pm the first Friday of each month.
1635 Broadway, 2nd Floor
Urban Stitch Boutique is a perfectly Oakland place. Its co-owners, Alanna Rayford and Winnie Anderson, curate styles from Bay Area and international designers with affordable prices and sustainable sources. The high windows light up this second-floor boutique with a welcoming and bright vibe. The space is full of tempting nooks and crannies, as well as a careful selection of everything you might need. Its Instagram showcases new arrivals, including colorful sandals, handmade jewelry, and dresses. Stop by and support this lovely, local business.
This opulent Art Deco extravaganza first opened in 1931, but suffered decades of disrepair before being fully restored. The Paramount reopened, phoenix-like, in 1973, and now houses the Oakland Ballet, the Oakland Symphony, occasional crooners like Norah Jones, and classic movie nights, like Wizard of Oz (screening Dec 30th). If you hate music and ballet, and movie classics give you heartburn, at least take the two-hour tour ($5) of the grand space. Get VIP access in, around, under, and over the secret stairs, pulleys, organs, and trapdoors of this glorious old beast.
1714 Telegraph Ave
Get your feet and heart in line with a stop at SoleSpace. Half shoe boutique, half arts lab, the Uptown location was created by Jeff Perlstein and Favianna Rodriguez in 2012 to keep your feet looking good while also offering an accessible place for community events. Specialty sneaks, DJs, arts events, and local gear make this the spot to start off your weekend in style.
Sign up here for our daily San Francisco email and be the first to get all the food/drink/fun SF has to offer.
1. Small Wonder37 Grand Ave, Oakland
2. Kingston 11 Cuisine2270 Telegraph Ave, Oakland
3. Sweet Bar Bakery2355 Broadway, Oakland
4. Dogwood1644 Telegraph Ave, Oakland
5. Duende468 19th St, Oakland
6. The Legionnaire Saloon2272 Telegraph Ave, Oakland
7. Drake's Dealership2325 Broadway Auto Row, Oakland
A plant-filled, mural-covered, vintage furniture-littered oasis in Uptown Oakland, Small Wonder is, well, no small wonder. Tunes from records waft in the air as diners share small plates like artichoke dip and fish tacos, and mains like prosciutto pizza and the open-face roast chicken sandwich. Colorful and friendly, Small Wonder is a versatile spot, providing an ideal location to sip coffee with a book, impress a date, or catch up with friends over inventive drinks.
Owner and Chef Nigel Jones was raised in Kingston, Jamaica, and he blends the bold, aromatic flavors (garlic, ginger, cinnamon) of his native island with Oakland’s organic ingredients to create a uniquely bracing menu in this airy, colorful Uptown space. The lineup features standouts like jerk chicken that’s marinated and smoked for hours before being paired with sweet plantains. The rich, slow-simmered curried goat is a must-try and, while it’s only prepared from Thursday to Saturday, worth planning your reservation around. Pair your pick with a Caribbean cocktail like the Cuba Libre with Angostura white rum and Mexican coke.
Sweet Bar is an airy, counter-service cafe with large windows overlooking Broadway and pumpkin ginger cupcakes that’ll keep you coming back for more. Owner Mani Niall sources all his organic ingredients locally to create sweet and savory treats like pot pie turnovers, focaccia bread sandwiches, sour cream cheesecake, and macaroons that'll quickly turn you into an addict. Bonus: there are lots of gluten-free goodies here, too.
This hip and cozy bar is serving up Prohibition-style craft cocktails (get the Bees Knees, a sweet & sour gin confection) and gourmet grilled cheeses (get all of them, but especially the one with truffle oil and/or whiskey bacon chutney). There's also a meat counter in the corner of the dimly lit, brick-lined space, where charcuterie and cheese plates are created -- perfect for sharing with a date at one of the communal wooden tables.
"Duende" means the spirit of passion in Spanish, and both the decor and cuisine at this stunning Uptown spot take that definition and run with it: the contemporary Spanish space sports chevron parquet floors, custom barstools and tables, and a soaring ceiling, setting a beautiful, intimate scene for an equally vibrant smattering of tapas, such as manteca colora (spicy pork rilettes) and bunuelos de queso (gruyere fritters). You can share these piquant dishes over a glass of wine or sherry from Duende's extensive selection. There are larger plates, too, like fideu caldosa: crispy rice-like noodles served in a pan with chicken, shrimp, and savory spices.
This divey two-story pub in Uptown Oakland is a one-stop shop for dancing, drinking, sports-watching, and general debauchery. There's rarely a cover and you'll find live performances or dance parties here most days of the week -- from hip-hop parties to comedy shows to Motown nights. This family-run spot gets bonus points for its old-school jukebox and pinball machines.
Although the founders have been brewing since 1987, Drake's Dealership -- named after English explorer Sir Francis Drake -- opened in 2015. The open, industrial space and denim-clad servers are a nod toward the building's history as a Dodge dealership. Drake's offers house-made, award-winning beer and wood-fired pizza.