Winston Pies – Brentwood

At Winston Pies, the answer to “Can she bake a cherry pie?” is definitely YES. Brianna Winston gave up being a lawyer to follow her passion, becoming a pie maker extraordinare. Initially Winston started her own business baking pies in her home kitchen, before branching out and setting up shop in Brentwood in 2017.


Winston Pies is along a busy stretch of Brentwood, down the street from The Tavern. The cute little storefront has seating for diners wishing to consume their pie on the premises.


The pie flavors are seasonal, locally-sourced, using organic ingredients wherever possible. All pies are made by hand from scratch, so they have that somewhat imperfect rustic charm.

Blue Ridge Blueberry

Most of the pies are fruit-based with a few exceptions. Pies are sold by the slice, 4-inch hand pie, mini 5-inch pie, whole 11-inch pie, and small bites available via special order. They even do gluten-free versions should that be something you seek.


The Dixie Classic Cherry pie (also pictured on the header) was not too sweet, letting the beauty of the fresh dark cherries shine through. It’s rare for a cherry pie not to be cloyingly sweet, with the filling thick with cornstarch, but this one seemed so pure, borderline healthy.

Harvest Apple Pie

The Harvest Apple Pie showed similar restraint on the sugar, with a filling more tart than sweet. The crust was so flaky that it broke when it was sliced.

Chocolate Cowgirl

The Chocolate Cowgirl was more in line with a classically sweet pie, its dark fudgy filling requiring a glass of milk. The crust, made of oatmeal, was like a oatmeal cookie, which made it more unusual.


If you like your pies to not be too sweet, Winston Pies are the perfect answer. Not only can she bake a cherry pie, she can bake blueberry, apple and chocolate pies, too.

Location – 11678 San Vicente Blvd, Los Angeles, CA 90049
Website –
Kid-Friendly – Yes
Kid’s Menu – No
Vegetarian Friendly – Yes
Vegan Friendly – No
Gluten-Free Options – Yes, by special order.

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