Martha Stewart Digs In: Judges Pie Contest at Popular Dutchess County Hotspot

Martha Stewart Supports Local Hudson Valley Businesses

It's no secret that Martha Stewart is part of our Hudson Valley community. There have been rumors of the famous homemaker living in the area for years.

Every once in a while we get a Martha sighting. And the coolest part is that she supports small local businesses.

In the spring of 2025, Stewart was spotted at the Millbrook Farmers Market trying different products like the juices from Chakra Bowls.

READ MORE: America's Favorite Homemaker Stops By Millbrook Farmers Market

Most recently Martha dined at the new Greek restaurant House of Stefas in Millbrook. Martha also frequents the award winning Stissing House in Pine Plains. She seems to be spotted there often.

Stissing House Hosts Pie Competition With Martha Stewart as Judge

We know it's not safe to assume, but we happen to think Martha happens to be a big fan of Stissing House.

She's been spotted dinning there a time or 2 and her latest venture at the Dutchess County restaurant has us wondering if our invite got lost in the mail.

According to a new Instagram post, Martha shared that she and 13 others were asked to judge a homemade pie competition of sorts at Stissing House.

View this post on Instagram

A post shared by Martha Stewart (@marthastewart48)

Here's the real kicker, there were 33 (!!!) pies in total for the judges to pick from. On Instagram Martha writes:

"Baked by amateurs these pies were set out on a vast table around a centerpiece of bales of hay and autumn leaves we were given 33 forks each and told to dig in my job was to choose with seven other judges the top three pies!!!!!

The homemaker adds "It was fun It was filling and it was not easy".  With that being said the judges were able to narrow down to 3 winners. It looks like a Dutch Apple Pie, a Shaker Lemon Pie and some sort of Pumpkin or Sweet Potato Pie were the favorites between the 13 judges.

Martha and her team will break down the event on her @MarthaStewartblog Instagram account. 

Fine Dinning in Dutchess County: Stissing House

Stissing House in Pine Plains is one of the oldest taverns in America.

The restaurant dates back all the way to 1782 and over the years has garnered recognition from some of the biggest food and leisure publications.

Stissing House was named one of the 50 Most Exciting Restaurants by the New York Times. Food and Wine named the restaurant one of the top 15 restaurants in the United States in 2025.

READ MORE: 243-Year-Old Dutchess County Restaurant Named Top Restaurant in the U.S.

Chef and Proprietor Clare de Boer was a James Beard Foundation semifinalist for Best Chef in 2024.

Stissing House is open Thursdays from 5 pm to 9 pm, Friday and Saturday 5 pm to 9:30pm, Sunday and Monday 5 pm to 9 pm. They're closed Tuesdays and Wednesdays.

Learn more at stissinghouse.com.