Theatrical Beginnings Turned Hospitality Masterpiece
It’s no wonder that Gregory Henderson and Joseph Massa have managed to transform The Roxbury into a captivating experience. Their rich backgrounds in theater production — a world where creativity knows no bounds — shine through in every room and detail. After all, who better to bring a sense of drama and whimsy to hospitality than two individuals who have spent their careers crafting compelling stories on stage? When they decided to buy the Roxbury Motel in the Catskills back in 2004, it was as if they were setting the stage for a new kind of performance, one where the guests become the stars of the show.
A Playful Ode to Pop Culture
Walking into one of the twenty-eight rooms at the Roxbury Motel feels like stepping into a fantastical, larger-than-life set, straight from the golden age of television. Each space is a love letter to the iconic TV shows and films from the sixties and seventies that defined a generation. It’s not just the bold styles and vibrant colors that impress; it’s the obvious care and attention to detail that Joseph and Gregory have poured into every corner. As a fan of retro pop culture myself, I can’t help but appreciate how they’ve managed to capture the essence of an era and make it feel fresh and fun. It’s a nostalgia trip that never feels forced, but rather, it feels like a genuine celebration of the past.
A Fairy Tale Come to Life
The Roxbury at Stratton Falls, located just two miles away, takes things to an entirely different level. Opening its doors in 2020, this enchanting property is inspired by the belief that fairies inhabit the property’s waterfall. And honestly, after seeing the place, it’s hard not to believe in a little magic. The themed rooms are straight out of a storybook, designed to make you feel like you’ve wandered into a real-life fairy tale. Staying in “Cinderella’s Gown” with its carved pumpkin bathroom and floating dress bed feels almost surreal — like you’re living a dream. As someone who has always loved fairy tales, I find this place utterly captivating. It’s rare to find a hotel that can make you feel like a kid again, filled with wonder and delight.
Spreading Joy Through Hospitality
Gregory and Joseph may have left the theater behind, but they’ve brought the joy of storytelling into the realm of hospitality with incredible finesse. The satisfaction they get from their work is palpable, even though it’s no longer about applause from a live audience. Instead, it’s about the smiles on their guests’ faces and the memories they help create. As someone who values experiences over things, I believe what they’re doing is truly special. They’ve turned their properties into more than just places to stay; they’ve created destinations where people can escape reality and immerse themselves in something extraordinary. That, to me, is the true essence of hospitality.