07/18/2026
DeFilippis Bakery & Café
The DeFilippis Family Story
Chapter Two: The Road to Middletown
When people ask how DeFilippis Bakery came to Middletown, the story really begins with my mother’s oldest sister, Contina “Connie” Siena, and her husband, John.
Like so many Italian immigrants, they arrived in America with little more than determination and a willingness to work hard.
They began their journey working in a restaurant in Coney Island. As the story goes, Uncle John started as a dishwasher and worked his way up to becoming a cook. Back then, that was the immigrant story—you worked hard, learned everything you could, and hoped an opportunity would come your way.
Aunt Connie was one of those remarkable people who seemed to recognize opportunity before everyone else did. She believed she and Uncle John could build something of their own, and that dream eventually brought them to Middletown.
In 1967, they opened Villa Siena Restaurant and Motel.
Many of you from Orange County probably remember Villa Siena. It became a wonderful gathering place for celebrations, great Italian food, and warm hospitality. The Siena family would go on to build a respected legacy in our community, and we have always been proud to call them family.
Some of my happiest childhood memories were made there.
I remember making the drive from Brooklyn to Middletown with my parents. My cousins and I would run through the motel, play tag before the restaurant opened, and laugh until someone finally called us in for dinner.
When everyone was together, there could easily be twenty or thirty family members around one table. Aunt Connie and Uncle John just kept bringing out platter after platter of food. No one ever left hungry, and no one ever left without feeling loved.
Looking back, those dinners weren’t just meals.
They were lessons about family, generosity, and taking care of one another.
As Villa Siena grew, Aunt Connie became convinced that Middletown was missing something.
Every visit ended the same way.
She would look at my parents and say,
“Middletown needs a real Italian bakery. You belong here.”
My father wasn’t so sure.
Brooklyn was home. His friends were there. The neighborhood, the Italian cafés, the familiar language, and the traditions he loved were all there. Leaving meant starting over from scratch.
But if you knew my Aunt Connie…
You know she wasn’t the kind of person who gave up easily.
And little by little…
She and my mother began planting the seed that would eventually become DeFilippis Bakery.
❤️ Tomorrow… we’ll share how one conversation became one leap of faith—and how a rundown building on East Main Street became the home of DeFilippis Bakery.
