Oakland’s Tiniest Bakery Gears Up for a Big Thanksgiving

One of the Bay Area’s tiniest and most beloved bakeries is hidden away, literally underground, in an Oakland basement. 

If it weren’t for the customers who routinely line up on the sidewalk outside, most people wouldn’t ever guess that Gregory’s Gourmet Desserts even exists. “Only two persons inside at a time,” the sign taped to the door stipulates. Once you step inside, the reason for the rule becomes self-evident: The bakery can’t hold much more than that. Not “so much a store as it is a storage nook,” as I wrote after my first visit back in 2014. 

Now, as then, every square inch of the space is crammed full of sweet delicacies: cookies, cobblers, cream pies and — most famously — about 16 different varieties of what regulars swear is the most delicious cheesecake in the Bay. 

Owner Gregory Williams, who’s run the bakery out of the same basement since 2000, acknowledges that his business has long outgrown the space. But even as he added a second Gregory’s location in San Ramon this summer, Williams can’t see himself ever leaving the OG underground location.

“It’s like a God-ordained space for me,” he says.

Williams explains that long before he ever became a professional baker, he randomly came across the 23rd Street building at least two or three other times. Every time, he’d stand outside and ask himself why it looked so familiar.

“It was the only place in Oakland that had the feel of a brownstone in Brooklyn,” explains Williams, who grew up in New York. And in 1999, when his landlords heard he had started baking and asked him to check out a space they owned, it turned out to be that very same building. It wasn’t a bakery at the time — “just a gutted basement that had a whole bunch of boxes,” he recalls. 

But to Williams, it felt like fate. He’s been selling his cookies and cheesecakes out of that basement ever since.

Over the next couple of weeks, Williams and his staff will be gearing up for Thanksgiving, by far the bakery’s busiest time of year, when they churn out a couple thousand pies in a three-day span. Bestsellers include classics like pumpkin pie, pecan sweet potato pie and a nutmeg-forward peach cobbler, which many loyalists (including this reporter) consider to be one of the finest in the Bay. Then there are seasonal cheesecakes, like a pumpkin kahlua cheesecake and a version made with brandy and eggnog.

This year, Williams is also pushing a few nontraditional holiday desserts he recently added to the menu. There’s his ube cheesecake, with its earthy flavor and eye-catching Valkyries-purple hue. And then there’s what he’s calling the “U Crazy Coconut Cake,” which comes layered with fresh strawberries — a tangy, relatively light counterpoint to all of the heavy fall flavors that tend to dominate the Thanksgiving table, Williams says.

Customers who preorder their Thanksgiving cheesecakes and pies can pick them up in Oakland or at the new bakery in San Ramon — which regulars at the original shop might be surprised to learn isn’t in a basement. Instead, it’s located in a somewhat hard-to-spot corner on the second floor of a big office plaza.

“It’s like I can’t find a street-level place,” Williams says, laughing. “Now I’m on the second level. We have all kinds of light. It’s amazing.”

Thanksgiving pre-orders at either Gregory’s Gourmet Desserts location must be placed online by Thursday, Nov. 19 — and ideally sooner, as the bakery may reach capacity. The original bakery is located at 285 23rd St. in Oakland. The new location is located at 2410 San Ramon Valley Blvd. Ste. 140 in San Ramon.