By the time the pies left Kingston, they had already taken three days of work.
On the first day, Nikki Freihofer made the dough and let it rest. On the second, she rolled it out, crimped the edges and eased it carefully into pans before freezing the shells. On the third, she blind baked the crusts, let them cool and filled them with a single layer of custard — simple and unadorned, the way she’d done it every Thanksgiving for about a decade.
Then she climbed into the passenger seat of her partner’s car, stacked the pies on two oversized sheet trays — two on her lap, one at her feet — and talked him through every curve between Kingston and Pine Plains.
“I had them stacked on my lap and was very much, you know, my partner driving through the windy roads, like, drive slower, slow down,” she said. “You know, making sure that they weren’t, like, wobbling around.”
Alex steered them over the Rhinecliff Bridge and along the back roads into town. As they turned into the parking lot at Stissing House, she bailed out. Inside, the three pies she’d guarded at her knees would be judged in a culinary competition called Pie Fest — and, to her surprise, taste-tested by Martha Stewart.
On Sunday, Nov. 16, Stissing House — the 1782 tavern at the center of Pine Plains — hosted Pie Fest, an amateurs-only pie championship created in partnership with Substack and chef-restaurateur Clare de Boer, who runs the restaurant and writes the newsletter The Best Bit. Organizers described it as a kind of Hudson Valley “Bake Off,” squeezed into the low-slung dining rooms of a Revolutionary-era inn.
From more than 100 applications, 33 bakers were invited and asked to bring three pies apiece. They came mostly from the region — New York, New Jersey, Connecticut, Massachusetts — and lined a long, hay-framed table with apple pies, custard pies, citrus pies and careful crusts that tried to catch the light.
Fourteen judges — including Stewart, Samin Nosrat, Claire Saffitz, Tamar Adler, Aminatou Sow, Dan Pelosi, Emily Weinstein, Greta Caruso, Hannah Goldfield, Ignacio Mattos, Jessie Sheehan, Katie Kitamura, Lidey Heuck and Rebecca Ellis — had an hour to taste the pies and half an hour to deliberate. Somewhere in that tide of sugar and butter, Freihofer’s salted maple custard pie came out on top.
“Yeah, it feels pretty great,” Freihofer said a few days after her win. “It’s very sweet and very special. You know, it was definitely a surprise to see Martha there. I was already excited and honored to be there with all the other awesome contestants.”
She admired the judges already on the list, “idols and icons in the baking and food worlds,” she called them. “That was a treat enough,” she said. “And then, you know, watching Martha appear was the cherry on top.”
“Honestly, it was not hoping that I won,” she said. “Like, I think, honestly, my true desire was to just prove to myself that I could do it up to my own standard.”
The pie was the same one she’d been making for years.
“This particular pie, I’ve been making every Thanksgiving for, like, 10 years,” she said. “It’s a very simple pie. It doesn’t have any decoration. It’s just one layer of custard.”
Freihofer, who lives in Kingston and is originally from Chicago, works inside restaurants — just rarely in the kitchen.
“I am a full time restaurant and hospitality consultant, so I do menu strategy and brand strategy for restaurants and hospitality businesses around the world,” she said. “So I spend my whole day and life in restaurants.”
Last year, she and Alex launched The Rolling Cones, a small seasonal soft-serve business run out of an Airstream trailer in Kingston.
“I’ve always loved baking and pies,” she said. “I jumped at the opportunity to do it in this context.”
Her Pie Fest entry took three days of steady attention — mixing, rolling, freezing, blind baking — with one goal: consistency.
“I wanted to make three that are, like, identical, like, they look exactly the same,” she said. “Professional level of consistency.”
Instead of inventing something ornate, she stuck with the pie she trusted.
“There was some really stunning pies both in flavor and in decoration,” she said. “And mine is just extremely straightforward. I’m not gonna mess with success.”
That confidence may run in the family.
“My great-grand great great grandfather started Freihofer’s Bakery,” she said. “It’s kind of in my blood to be a baker.”
For Stissing House, Pie Fest was a way to fuse local agriculture with a national online food community. Food and drink newsletters on Substack now have tens of millions of subscribers; Pie Fest offered a real-world expression of that world, with a Substack residency and a menu spot for the winning pie as part of the prize.
Katie Pearce, Stissing House’s director of feasts, produced the event with de Boer and Substack.
“We thought it would be great to have an amateur’s only competition and really get some, like, powerhouse type experts and icons on a judging panel,” she said.
The day also doubled as a showcase of Pine Plains’ farm network. Steel Bow Farm provided hay bales for the dramatic pie table; Chaseholm Farm would later feed pumpkins to its pigs. Montgomery Place Orchards supplied apples. Sparrowbush Bakery provided bread and butter.
The judging was serious. The 14 judges were split into two panels: a “crowning jury,” which included Stewart, and a “naming jury,” which awarded superlatives like “flakiest crust.”
“There wasn’t like, a scale or, like, a point system,” Pearce said. “It was more just conversation.”
Tamar Adler, the Hudson Valley food writer, said the criteria were clear.
“All good pies have a flaky crust and enough salt to counteract sweetness,” she said. “One-note sweet won’t cut it.”
When it came time to choose a winner, judges found themselves surprisingly aligned.
“Incredibly, we were all in agreement about the top three pies!” Adler said. At one point, she added, Stewart’s opinion began carrying extra weight — “counting as several” votes — tipping the final decision.
“Martha took charge of the whole thing,” Adler said. “She insisted we all look at all the pies before anyone took a bite!”
Freihofer saw the same thing from across the room.
“She was just such an ethereal creature,” she said. “She circled around the table, she took photos of every pie. She treated it as a job.”
A tiebreaker was even called for the top two pies. In the end, Freihofer’s salted maple custard pie edged out a Shaker lemon pie for first place.
Winners didn’t go home with cash.
“We really wanted to give away homewares and bragging rights and keep it pretty low stakes,” Pearce said.
First place came with dinner at Stissing House and a custom stoneware plate. Second went to baker Lauren Hildreth with an Amish pie basket. Third place — awarded to a 7-year-old named Rosie — came with Shaker boxes filled with small treats.
Rosie’s Dutch apple pie earned a roar.
“That moment was just so spectacular,” Pearce said. “It was so heartwarming. You win something at that age, and it could really define your direction.”
Since the event, one question has lingered long after palates were cleansed: Will Pie Fest happen again?
“That’s a really good question,” Pearce said. “Sometimes when these things happen and go off so much in the right way … it’s almost really hard to replicate that ever again.”
Want to make the winning pie yourself this Thanksgiving? Read the recipe here.