jairo triguero
Jairo is a proud lifelong resident of Sleepy Hollow, having called the village home for over 25 years. A product of the local public schools—from John Paulding through Sleepy Hollow High School—Jairo has deep roots in the community and a firsthand understanding of the changes and challenges the village has experienced over the decades. He grew up on Beekman Avenue in the heart of Sleepy Hollow’s downtown and has always remained closely connected to the place he calls home.
Jairo is best known to many residents through his work managing Grape Expectations, a local favorite where he has spent years building meaningful relationships, hosting community events, and supporting local causes. Whether catering fundraisers, helping organize celebrations, or simply chatting with neighbors, Jairo is deeply engaged with the everyday life of Sleepy Hollow residents.
Professionally, Jairo trained at the Pennsylvania Culinary Institute and has worked in the food and hospitality industry across the country—from high-end catering events like the Jack Nicklaus Golf Tour in Ohio to revitalizing menus in restaurants in Miami, New York City, and right here in the Rivertowns. No matter where his career has taken him, Jairo has always returned to Sleepy Hollow—drawn by its history, diversity, and sense of community.
Jairo is running for Village Trustee because he believes that strong leadership starts with listening. He is committed to representing the voices of all residents and helping guide thoughtful growth while preserving the charm, affordability, and inclusivity that define Sleepy Hollow. With deep community ties and a passion for public service, Jairo is ready to serve and make a difference.
Why I’m Running for Trustee
Now, more than ever Sleepy Hollow has to listen to her residents!
With less than two weeks until this year’s election, I would like to reintroduce myself. My name is Jairo Triguero, and I am a candidate for the Sleepy Hollow Board of Trustees.
I am a proud lifelong resident of Sleepy Hollow. Many of you know me from our days together in school, from around town, or even through the community fundraisers I attend and work. But most people know me from Grape Expectations, where I have served the community for 20-plus years and managed every aspect of the business over the last 14 years.
Working as a sommelier and wine merchant, I spend the majority of my time listening to people and doing my best to find solutions and accommodate their needs. This doesn’t always amount to just helping someone choose a great bottle of wine – many of my customers open up about their lives and what gripes they’re having with the Village.
I don’t really discuss my personal life, as I have always been taught wisdom comes from listening to others. My mother is Dominican. My father is Colombian. My godparents are Ecuadorian. This does not define me, but as a first-generation American born here, they have each opened my eyes to what goes overlooked in Sleepy Hollow, especially among those communities.
Listening and learning from my neighbors and customers has taught me so much about what’s missing across the spectrum, and what changes would make the biggest differences. Whether it’s finding a parking spot at night, trying to open a new business, trying to keep one afloat, or simply being able to afford to stay in this great Village, these problems are real, and they affect our lives.
In a homogenous gathering, differences are strengths. Listening has more long-term benefits than not listening. And when you become a community, there is always a hand reaching back or lifting you forward. By serving on the Board of Trustees, I would be honored to become someone who is better positioned to make impactful solutions a reality.
Sleepy Hollow is five square miles and filled to the brim with people from every walk of life, bringing a plethora of life experience and expertise to the table. It’s changed so much since I was younger, and yet it’s very much the same. The potential for its future is limitless.
This slate, gifted in our own rights, has the connections to create something more than any four people could alone. Let us show strength by embracing our differences and bettering our Village together. This is why I urge everyone to go out on November 4th and vote. And I humbly ask you to help us put our best foot forward as we walk into Sleepy Hollow’s future together by voting for Marjorie Hsu, Jared Rodriguez, Cory Krall, and me, Jairo Triguero.
