Martha Stewart, Surprise Judge at First Stissing House Pie Fest

The Stissing House’s first-ever Pie Fest, November 16, already had the makings of a Hudson Valley classic: 33 home bakers, a table dressed in pumpkins and hay bales, in a 243-year-old tavern whose kitchen has been feeding Pine Plains since the 18th century. Then Martha Stewart arrived, slipped into the judging panel, fork in hand, ready to taste every single pie.

“I knew there would be a lot of pies,” Stewart wrote afterward in her blog. “But I never thought there would be 33 to judge. Good thing I did not eat a big breakfast!”

The festival, organized by Stissing House’s current steward, chef-owner Clare de Boer and co-cookbook writer Katie Pearce, drew contestants from across the region and transformed the historic dining room into a pastoral gallery of crust and filling. Judges, including authors, chefs, and bakers, worked in two panels, one to hand out superlatives like “flakiest crust,” “best decoration,” and the other, led by Stewart, to choose the top three winners.

The top prize went to Kingston-based baker and hospitality consultant Nikki Freihofer, who says learning that Stewart was among the judges sent a shock through the room. Freihofer took home the victory with her salted maple bourbon pie, a Thanksgiving staple she’s been making for a decade. 

Stewart praised the custard-based dessert for its “perfect balance of salty and sweet,” calling it “delightful, comforting, and delicious.”

Second place went to Lauren Hildreth for her elegant Shaker lemon pie, with its thin citrus slices and tender crust. In third, a seven-year-old baker from Connecticut stunned the judges with a Dutch apple pie that Stewart described as “classic” with a “delicious chunky crumb topping.”

Though the prizes included bespoke pottery, dinner at Stissing House, and Amish-made pie baskets, Pearce emphasized that the contest was designed to be joyful rather than high-stakes. 

Still, the judging was serious. Food writer Tamar Adler told the New Pine Plains Herald that the panel was quite aligned; “Incredibly, we were all in agreement about the top three pies,” Adler says. Freihofer recalled how focused Stewart was, circling the long table, photographing every entry.

For Pine Plains, the new Pie Fest tradition felt like something truly special. It was a celebration of regional food, a showcase of local culinary talent, and a reminder of how much joy a simple pie can carry. Or, as Stewart put it in her blog post: “Fun and filling!”