Oakland, CA City Guide

by Sabrina Smelko


When I was in high-school, my home-town tripled in population in one year (which was record-breaking for North America). It was fascinating watching the soul and spirit of the town ebb, flow and grow. For Daniel Scovill and Adam Winig, this fascination is more of an actionable passion. Since 2003, they have been designing, developing and building as the Principal Owners of the architecture and design firm Arcsine, but today, they’re stepping back from their blueprints to tour us through Oakland, a town that continues to inspire them as it grows.

Adam’s attraction to Oakland is an electric one: he loves the up-and-coming energy it radiates and how — despite the countless things there are to do, see, eat and drink–, it feels like a small city. For Daniel, Oakland continues to lure him in with the variety it boasts: from the gritty and vibrant port and street art, to the incredible food and beverage offerings, entrepreneurial businesses, and the secluded trails in the Redwood Regional Park. Oakland always has surprised and gems to be discovered, and due to the location, being smack-dab in the middle of the Bay Area, it’s been an amazing place to grow their business. Today, Adam and Daniel are sharing their favorite Oakland locales and the places that inspire them throughout town, broken down by region. –Sabrina

i. Region Name: Jack London Square

outdoor movie at jack london

Situated along the Oakland/Alameda estuary, Jack London Square is a cultural hub and a symbol of the city’s history as a seaport. From summer night markets and outdoor movies to kayaking and bicycling along the waterfront, Jack London Square is a hot spot for dining, boutiques and year-round events. It’s one of Oakland’s most identifiable landmarks.


Jack London Square is the ideal place to meet up with friends for food and drinks. Stroll along the waterfront, rent a bike and explore the Bay Trail, or just relax outside and watch the boats go by on the water.

plank at jack london


Every Sunday, Jack London Square waterfront is home to this great outdoor farmers’ market that offers the best of California’s agricultural bounty. You can find fruits, vegetables, as well as freshly baked breads and pastries, delicious specialty foods and fresh flowers.


If you love Italian food, make sure you stop by Lungomare. The menu offers a blend of Tuscan and Ligurian specialties: a mix of seafood, house-cured meats, rustic pizza and fresh pasta, with dishes locally sourced whenever possible. It also has an awesome cocktail bar and the most incredible waterfront views.

i. Region Name: Old Oakland

The old Victorian style buildings in “original” downtown area date back to the 1860’s. In the past few years a lot of new bars and boutiques have cropped-up in the historic district, making it a great stop to explore and shop.



Stroll the pop-up and new shops of Old Oakland.


Crown Nine has beautiful jewelry designed by the talented Kate Ellen. A favorite piece from there is a bronzed nail that she found in her building from circa 1900 and fashioned into a bracelet.

Umami Mart is an amazing Japanese store for bar and kitchen goods. They have the most stunning range of glassware and bar tools for the budding mixologist.

Also check out the Old Oakland Farmers’ Market on Friday mornings along Ninth Street.


The Front Bar at The Trappist is one of our favorite watering holes (in the world). Whether you go for a Monk’s Lunch in the middle of the day, or an evening for several rounds; this intimate establishment will make you a Belgian and specialty beer aficionado after the first sip.

Wine and whiskey lounge District offers an eclectic selection of wine, whiskey and small plates and they constantly roll vintage movies on the walls.



Try the grilled vegetable tacos and grilled vege torta in the market-hall like setting of Cosecha. And their aguas frescas are always on!

ii. Region Name: Downtown

The Downtown area is Oakland’s Central Business District, bustling with restaurants, bars and nightclubs.


If you’re into radio and podcasts, you’ll find the home base of many within a small five block radius; (99% Invisible, Snap Judgment, Youth Radio, Popup Archive, Radio Ambulante, Radio Bilingüe, Making Contact, etc.)


E.M. Wolfman General Interest Small Bookstore is a brilliant little independent bookshop with a small art gallery in back. Poetry readings, obscure titles, and always a great conversation to be had with the proprietor & founder, Justin Carder.

Forget the tacky tourist t-shirts and pick up something cooler from Oaklandish. Their original designs are hand printed here in Oakland and proceeds support their ongoing public art and action campaigns.


Radio is our favorite dark downtown bar. Even after the slick new storefront glazing was added, the black shades were installed. Grab a beer, play some pinball and enjoy the some freshly spun Whitesnake records on the speakers.

Drexl is our current love affair! Before a show at the Fox, after work, or for an evening of cocktails, have one of the talented mixologists do a “Dealer’s Choice” with one of the unique gin varieties from neighboring Alameda’s own St. George Spirits’. Then take your drink up to the mezzanine and play a round or two of skee ball.



Head over to Ratto’s International Market & Deli for lunch. It’s a perfect place for a wonderful sandwich and street side seating in Old Oakland. The market has the charm of the early 1900’s and the place is 4th generation family owned and operated.

Sobo Ramen is a quaint ramen café that focuses on local food sources, including custom noodles, and even includes vegan and gluten-free offerings. Prepare for a long line if you drop in for lunch on a rainy day.


For dinner, try Tamarindo for a traditional Mexican feed or Xolo taqueria which is also open late night and features old posters of Mexican wrestlers and bull fight advertisements.

ii. Region Name: Uptown


Eat, Drink, and enjoy a show at the historic Fox Theater. This gem of Oakland brings great concerts to downtown Oakland in a stunning example of 1920’s architecture.

Arcsine_Oakland_Fox Theatre

Check out Oakland First Fridays and Oakland Art Murmur on the first Friday of each month, where they close off the streets for art studios, pop-ups and food trucks. Enjoy the art and people, it’ what Oakland is all about!

Also, be sure to stop by FM on 25th Street. A collective of brilliant artists and exemplars of young Oakland artists.

Shop: Owl-N-Wood is a Danish-inspired spot is with gorgeous furniture and murals that sells select vintage clothing and accessories.


Modern Coffee – a taproom for coffee! With rotating featured roasters, Modern serves up coffee and espresso as it should be. You will learn about new roasters from all over and the friendly crew at Modern will welcome you like you are an old-time regular!

Arcsine_Oakland_Misha Bruk_Modern Coffee

Grab one of the best cocktails in the East Bay area in the art deco setting of Flora. They also offer classes if you want to learn how to make your own.

Also stop by Plum Bar for a cocktail for yourself –or share a punch bowl with a friend (or four).


Check out Rudy’s Can’t Fail Cafe, a popular diner that has deep roots in the punk-rock scene. It’s actually named after the Clash song and part-owned by Mike Dirnt from Green Day.

Arcsine_Oakland_Rudy's Can't Fail

Duende is Chef Paul Canales’ Basque-inspired restaurant. You’re sure to find incredible dishes that celebrate local, seasonal food and Spanish flavors. Paella, amazing art and sculpture, and lovely Calvados cocktails are to be enjoyed! Paul will likely drop by and have a chat with you. Ask about the progressive Jazz and flamenco events up on the mezzanine, and buy some Spanish wine from their Bodega before heading home.



Hotels :

Oakland’s hotel renaissance is yet to begin. In the meanwhile, go Airbnb and live like a local.


Boot & Shoe Service for breakfast, a pastry and coffee, or exquisite pizza and other superb dinners. Go early with the kids or later in the evening with friends and it never disappoints. Sometimes we even go there late, with our sketchbooks, and sip on a Black Lodge in the back with the amazing bar staff. Be sure to doodle a sketch or write some prose on the back of your receipt, roll it up tightly, and tuck it into a crevice between the brick on the café side.

Brown Sugar Kitchen in West Oakland, get the grits with poached eggs and a waffle with their homemade butter and apple cider syrup.

Portal Oakland at Lake Merritt. After a Saturday morning stroll around Lake Merritt, drop in for brunch on the patio. Have their bottomless mimosa or a tasty cider and enjoy the incredible brunch selection of all stripes, as well as heaps of vegetarian options.

Rowdy yet refined, Penrose offers wood-fired Californian cuisine & a creative cocktail menu in a striking space with communal tables.


Grand Lake Theater. Movies on Friday and Saturday nights in the main theater start with an organist playing classic tunes and scores from movies. The art-deco architecture and neon marquee is a landmark of Oakland.


Take the kids to the planetarium and museum at the Chabot Space & Science Center, and then go stroll the trails in the surrounding Redwood Regional Park. Also go at night to look through their collection of telescopes.

Go to the Oakland Museum of California on a Friday night for half-price gallery admission, street food trucks and live DJs. OMCA’s brilliant galleries share the rich history of California.

Discover the charming pedestrian alleys of Temescal Alleys. Stroll the shops, feast on the best filled donuts around, and get your beard trimmed at the barbershop.

Your head may explode with all the options at Eat Real Festival, and certainly your belly will. An annual food & drink festival held in September that you definitely don’t want to miss.


Suggested For You


  • Kate Ellen at Crown Nine designed my engagement ring and my husband’s wedding band. She’s amazingly talented and a real treat to work with. So glad to see her featured here!

  • Um, I know this can’t be a guide to everything ever about Oakland, but I’m pretty sure there are actual things to do in Downtown Oakland besides the random WTF factoid about radio & podcasts that’s not an activity that this guide lists. First Fridays & Artwalks, for example.

    Also, a typo/something that’s really confusingly written: Rudy’s Can’t Fail Cafe has two locations, the original one in Emeryville and the one in Uptown. This guide sounds like it’s recommending a spot in Emeryville rather than the Uptown location.

    Do the writers of this guide actually live in Oakland or was the research for this piece done over the internet?

    • Kira

      Yes, these writers live in Oakland and it is their curated guide to how they would spend 24 hours in their hometown.

      We publish multiple “24 hours in” guides* to cities on purpose, to show different perspectives on cities. If I’ve learned anything from publishing city guides for the past 10 years it’s that no local seems to agree on any list, even if they’ve lived there their entire life.

      (*Here’s another take on Oakland, for example)

      So the snark isn’t necessary here- if you don’t like the guide you’re welcome to submit your own guide to serve as an alternative.


      • Well handled, Grace! I’m a local who is very pleased to learn about the podcast hub. Hope I get to see Glynn Washington walking around one of these days!

      • Grace, excellent reply! Oakland is awesome and constantly changing with discoveries to be had at every turn. Your guide rocks for someone who has not visited the area and locals alike. Thank you for sharing your perspective on The Town.

  • Spots that should have also made the list if there was room:

    Everything and anything on Piedmont Avenue. From the Indepedent Piedmont theater, to Cato’s Ale house for trivia nights to their awesome Comic and Games store.
    For some amazing views, you can also walk around Mountain View Cemetery, at the top of Piedmont Ave. Sounds morbid but it’s a beautiful spot to walk around and reflect.

    Also, there are amazing hikes in the Oakland hills. Anything along Skyline Blvd. and near Joaquin Miller park.

    Lake Merritt is a magical spot to walk around and Children’s Fairy Land is a MUST for those with kids. It was what Walt Disney based Disneyland off of.

    In the Laurel district, be sure to check out Communite table, an amazing restaurant that just opened and has amazing take away foods in bulk when you don’t feel like cooking.

  • Yay for the Bay Trail shout out! I work for the agency that makes that happen.

    I love a lot of these places and found a new one (Modern Coffee) though I will argue to the death that Cosecha is better than Tamarindo!

    Shakewell is new, and in my neighborhood, and the owner is one of the nicest people you’ll ever meet. So I had to add them in too.

    Oakland love!

    • I love Oakland but was shocked to see Emeryville’s Rudy’s Can’t Fail Cafe listed as in Uptown Oakland. That mistake should be corrected. Emeryville is one of the few towns that has not been gobbled up by Oakland’s expansion over the past 150 years. Emeryville pride.

        • Yes, I know.

          It should say that in the text instead of this:

          “Check out Rudy’s Can’t Fail Cafe, a popular Emeryville diner that has deep roots in the punk-rock scene.”

          • Bee

            The text should say whatever the writer intended, which, in this case, was to mention the downtown location. I’m sorry if this mention has upset you. As I mentioned before, I’m happy to provide your version of the city if you want to add your voice. But to say what another person’s personal guide to a city “should” say is not the same. You’re welcome to provide your own version if you want to drop us a line and participate.


            • Grace, writers should not intentionally confuse readers if they want people to find their reviews and information useful.

              Emeryville is not a downtown location because it is not in Oakland, just like a Staten Island location is not a Brooklyn location. Just sayin’.

            • Bee

              I don’t think anyone seems confused by this, save for your comment. There are TWO locations, one of which is in Oaklans.

              I’ll end this discussion by pasting in a line from Rudy’s own website, “Rudy’s is a modern diner in Oakland and Emeryville, California.”


  • Great piece on Oakland but very secular.
    Sticking mostly to downtown. The taco trucks of East Oakland are the stuff of legends. You will never look at a taco the same again, or a cows tounge. The writers really need to take a trip down to the the flat lands!

    • Hannah

      We have another perspective on Oakland here, too. And we always welcome new 24 hour guides from any local who wants to contribute and represent another take on their home town :)


  • Personally, I love these little glimpses into someone else’s life. There are a million versions of Oakland, one for each person who lives here and each person who visits here. It’s lovely to be able to learn from someone else’s version, even more so if that person’s is very different from yours.

  • Thanks for all these great suggestions for Oakland! There is so much to check out in this diverse and creative city. I’d like to add Creative Growth Art Center on 24th to the list — a great organization that supports artists with disabilities — always a fun time on First Fridays / Art Murmur nights!

  • FWIW, I too think the Rudy’s description is confusing. While there is an Uptown Oakland location, and the photo of it in here is from that location, the text says, “Check out Rudy’s Can’t Fail Cafe, a popular Emeryville diner.” Emeryville is a totally different city. You could mention that the original location is in Emeryville, or just drop the Emeryville reference altogether, so everyone is clear you’re talking about Uptown Oakland’s Rudy’s. There is no issue with this writer’s picks—they’re great. The issue is that the writing/editing of the description of Rudy’s is likely confusing for those unfamiliar with the East Bay. If they go to map “Rudy’s in Emeryville” on their smart phone, they’ll leave Oakland. I find the tone of Grace’s responses disappointing. Like me, these readers are just trying to help you out and improve the usefulness of your guide by fixing a small oopsie.

    • Elle

      I’m sorry if my tone was off-putting. I found the tone of that particular commenter to be off-putting and sometimes that can get to me after a long day.

      City guides are always problematic and I’ve yet to find a way to prevent them from becoming arguments between locals. I don’t publish every comment that comes through and more often than not a lot of them that get deleted are trying to attack the guide writer (or me) for a laundry list of reasons that usually devolve into cursing and personal attacks.

      Sometimes that gets to me and I wish people could take a deep breath and think about the time the guide writer put into their work before attacking them. Maybe I needed another deep breath before responding, too.

      My apologies if my tone felt too harsh for a correction. I feel my guard go up any time we publish a guide and I have to start stepping in to deal with the “Do you even LIVE here??” type comments that happen no matter who writes the guide.


  • So glad to see Oakland featured here on DS and so sorry people have to be bickering over this! I love the Town and all I want to see is more recognition of how great it is here. Let’s chill.

    Now, to add to this list, I would also recommend:
    – In Uptown, the beautiful and historic Paramount Theater for classic movie night, comedy shows, orchestral music, and more.
    – In Downtown/Lake Merritt, the Oakland Museum of California. Great for families and singles alike, especially on Fridays when it turns into a block party.
    – In Old Oakland, I also recommend End Game — an awesome gaming store that has fun in-store gaming all the time. You can find anything from little kid wooden puzzles, to card games, to miniatures, to Euro board games, to RPGs.
    – In KONO (not mentioned here), go to Gogi Time for Korean BBQ. They have a hot pot, too, but the barbecue is so good we just can never bring ourselves to try it… yet.

    I have so many favorites, I guess I should submit my own 24-hour guide… Hella <3 Oakland!