The sweet (but not too sweet) story of how Mary Alisa's chocolate cake went from family favorite to famous

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More than 1,300 cakes later, Sherman is as happy making the chocolate confections as she was when the restaurant opened in the fall of 2021. 'I L-O-V-E it!' she says. 'I can be corny, but I feel like I'm living in a Christmas Hallmark movie. I love making people happy with it.
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To maintain quality, Sherman makes each cake individually. The ingredients are: King Arthur flour, high-quality cocoa powder, sugar, baking powder, Kosher salt, oil, whole milk, pricey Nielsen-Massey vanilla, and white eggs.
David L. Ryan/Globe Staff
'The best time is in the restaurant — people don't know who I am — I will see someone eating it or sharing it, and they have smiles on their faces.'
Before it made the menu, Sherman's cake was vetted by Cosmo Goss, The Winsor House's executive chef. It was never meant to be a permanent menu item.
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'I frankly thought it was a special thing we could do for the opening,' says Chris Sherman. 'My biggest fear was that people wouldn't like it. Then we started reading reviews and online comments where people said, 'You have to try the cake.' After four years, it's still a hit.'
The cakes are prepared at The Winsor House kitchen well before the restaurant opens.
David L. Ryan/Globe Staff
Sherman is becoming known around this historic shipbuilding town as the 'Cake Lady.' 'My only claim to fame is I've made a few whole cakes for Steve Carrell,' she says. 'I've never met him, but he has a house on the South Shore and he orders around Christmas.' (Attempts to reach the A-List actor for his take on the cake were unsuccessful.)
The cakes are prepared at The Winsor House kitchen well before the restaurant opens. Sherman makes at least 4 cakes every week — and up to 8, depending on demand. Summertime, when folks head to ICO's nearby outdoor raw bar for its famous oysters, often brings more customers to the restaurant. (The cake is not sold at the Island Creek Raw Bar in
In the kitchen of The Winsor House restaurant, Mary Alisa Sherman bakes the layers of her chocolate cake.
David L. Ryan/Globe Staff
To maintain quality, Sherman makes each cake individually. The ingredients are: King Arthur flour, high-quality cocoa powder, sugar, baking powder, Kosher salt, oil, whole milk, pricey Nielsen-Massey vanilla, and white eggs. 'It's easier to find egg shells in batter with white eggs,' she says. (The cake also includes a secret ingredient that can't be divulged.)
The frosting consists of sifted powdered sugar, cream cheese, Land O'Lakes unsalted butter, and the aforementioned vanilla. Sherman buys her own ingredients (stocking up at area grocery stores when items go on sale and relying on Amazon) and brings them in Tupperware containers to The Winsor House for mixing.
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The cake layers are baked for one hour and 15 minutes. After cooling, Sherman assembles the cake and gives it a
Cake pans cool in The Winsor House kitchen.
David L. Ryan/Globe Staff
Sherman's daughters are delighted at this new stage in their mom's life. 'I love how my mom can now share this piece of our childhood with her community,' says Elise Sherman. Adds Devon Daley, Elise's twin: 'It was a sacrifice for my mom to stay home with us. It was meaningful, but it's nice to see when people can pursue roles they're passionate about. Second lives can happen organically.'
Sherman grew up in Connecticut, moving to Duxbury in the '80s. Her professional career included a stint at a software company and a graduate degree in education and certification to teach Spanish. She's an active volunteer Duxbury history guide for schoolchildren and local assisted-living residents.
Mary Alisa Sherman frosts her chocolate cake.
David L. Ryan/Globe Staff
For 20 years, she was a South Shore representative for the Friendly Towns arm of The Fresh Air Fund, a nonprofit that paired underserved New York City children with families during the summer. (The fund this year began placing kids only in camps.) She and her 'crazy, supportive high school-sweetheart' husband, Chris senior, regularly hosted a child in their home.
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Now it's Chris junior who's her boss and who signs Sherman's paycheck. He always includes a message in the memo spot: 'Hey Mom, Hope you're having fun!'
Mary Alisa's Dank Chocolate Cake, $13 per slice, available at The Winsor House at Island Creek Oyster Farm, 390 Washington St., Duxbury, 781-934-0991.
Peggy Hernandez can be reached at
. Follow her on Instagram @peggy_hernandez
Mary Alisa Sherman decorates her chocolate cake.
David L. Ryan/Globe Staff

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