Established in the 1860s as Oakland’s Downtown area, rumor has it that you can still find remnants of the seamier side of the Bay Area in the basements of Old Oakland’s historic buildings - think underground brothels and boxing rings, off-track betting and Prohibition-era shenanigans and you have a pretty good picture of what this neighborhood was like back in the day.

These days the neighborhood is both quaint and happening. Brick sidewalks, leafy trees, beautiful architecture and uh-mazing shopping & dining are bringing this neighborhood to life. Throw in its convenient proximity to BART (a mere two-block walk from the 12th Street Oakland BART station) and it makes going out in this neighborhood easy.

To start:

Eat up, you have some shopping to do. Stop first at Caffe 817 for a light breakfast and a damn fine cup of coffee or tea. I love their Olivada Toast with poached eggs. And their cookies. Oh their cookies.

Fed? Energized? Ready? OK.

Marion and Rose’s Workshop - Owner/Quality Maven/Curator Kerri Johnson hand-picks all of the pieces in her airy and comfortable shop. Everything in here feels like a well-chosen piece that you’ll be able to keep for decades. That’s because Kerri focuses on heirloom-quality, American-made goods - pieces meant to last decades and transcend fashion or trend. Her shop is the go-to place for Field Notes, Faribault Mills wool blankets and linens by Shapes and Colors.

Maple Street Denim - Let's give a warm welcome the newest store on the block! Owner Julie Harleman offers a full-service denim store. You can expect personalized help to find the best fitting and best quality denim. Julie has 12+ years of experience and, as she puts it “I am passionate about helping people find good quality denim that fits well and makes the customer feel great about themselves.” She is committed to making the shopping experience relaxed, engaging and low-key. The denim in her shop will be selected for quality as well as manufacturing practices, with an emphasis on products that are sustainably and fairly made. Welcome to the neighborhood!

The beautiful jewelry selection at Crown Nine

Crown Nine - Jewelry. Tremendous, well-chosen, wearable and timeless jewelry. Owner and designer Kate Ellen Murphy carries a perfectly curated selection of jewelry designers from the Bay Area and beyond. Artists like Amanda Hunt, Marja Germans-Gard and T. Morgan Made sit alongside her collection of non jewelry objects like ceramics by Jo Boyer and, my personal favorite, perfume by Olo Fragrance. Kate works upstairs in her loft studio, creating her own collection as well as crafting custom wedding and engagement rings.

After shopping, you have your pick of adult beverages and food at District. They have an extensive drink menu, including whiskey flights - I recommend starting with their Identity Crisis flight, a selection of whiskey, rye and bourbon to find out which one you like best.

Also awesome? The Trappist. So many beers. So so many beers. It’s a perfect place to end or start your night.

The list of places in this neighborhood goes on - Umami Mart, FloraCultural Society, Miss Ollie’s, Tamarindo - you get the idea. If you are lucky enough to stop in Old Oakland on a Wednesday, look for Natty Cakes and her delicious cookie sandwiches in the breezeway between Marion and Rose’s and FloraCultural Society.

What’s your favorite spot in Old Oakland?