Chase DeFilippo

Growing up in a blue-collar family, I have worked alongside my father at New England Construction for as long as I can remember, gaining hands-on experience in nearly every trade—from carpentry and masonry to equipment operation and site management. These experiences taught me the value of hard work, responsibility, and problem-solving. I have also built on this foundation through internships in government and finance, automotive work at Cobra Automotive, hospitality positions at Encore by Goodfellas, and leadership as a ski manager and instructor at Powder Ridge. Each role strengthened my skills in teamwork, communication, and leadership. I am eager to pursue a business education to further develop these abilities and to one day create programs and opportunities that promote innovation, equity, and meaningful impact in my community and beyond.

From a young age, I’ve been deeply involved in both hands-on work and creative pursuits, shaping a strong sense of discipline, leadership, and curiosity. Growing up working alongside my dad in construction, I gained experience in nearly every trade and learned the value of hard work, problem-solving, and perseverance. Attending Trinity-Pawling Schoolhas been a formative experience, where I have grown academically, athletically, and personally.

As Head Tour Guide, I led campus tours for prospective students and families, and I worked with The Jed Foundationto raise mental health awareness across the student community. I play quarterback and middle linebacker in football, participate in competitive hockey and baseball, and ski recreationally for fun, which has taught me excellent time management and the ability to balance multiple commitments while performing at my best.

Musically, I am a lifelong guitarist inspired by Peter Frampton, performing gigs, writing original songs, and studying music theory to refine my craft. I have also taken initiative in creative projects like producing “The Stow Reality Show,”a project starring me and a few friends that captures life in our dorm, Barstow, at Trinity-Pawling. The show highlights the authentic experiences, friendships, and fun moments of everyday student life, giving me hands-on experience in collaboration, creativity, and storytelling.

Across academics, athletics, music, and leadership, I have consistently combined dedication, creativity, and initiative, preparing me to embrace new challenges and opportunities in college and beyond.

At Trinity-Pawling, I currently help the admissions team by giving tours to prospective students and their families. I show them around campus, explain daily life in the dorms, and share my personal experiences at the school. I also help answer questions and make visitors feel welcome, giving them a real sense of what it’s like to be part of our community. I have learned a lot from this experience, including how to communicate clearly, think on my feet, and connect with people from all different backgrounds.

I truly love doing it, and it has given me a sense of pride and responsibility. Being named Head Tour Guide has been an honor, and it motivates me to continue improving and helping others feel comfortable and excited about their potential school. I hope to continue similar work in college, sharing my experiences, supporting the community, and helping prospective students discover their own paths.