The Roxbury Experience

The story of The Roxbury Experience has it all: small-town beginnings, a stint in the Big Apple, finding true love, moving out of the big city to follow a dream, a fire, an epiphany in the desert — and then, finally, a magical place filled with fantasy, gold leaf, glitter and shimmer. Oh, and a success story as unique and creative as our protagonists, Gregory Henderson and Joseph Massa.

Husbands Henderson and Massa are the masterminds behind two of the most-talked about, internationally celebrated and Instagrammable properties in the world, The Roxbury Motel and The Roxbury at Stratton Falls. Tucked into a sweet pocket in New York’s lush Catskill Mountains, the properties are two miles apart and guests of either are encouraged to indulge in the amenities of both, which include spas, pools and the restorative nature of, well, nature. Conde Nast Traveler raves about it. “CBS Sunday Morning” recently aired a feature on it. New York Magazine was an early fan.

Henderson grew up in Duncan, Oklahoma, where his mother lived (though she’s now in Edmond). and spent quite a bit of time in Oklahoma City, where his father and stepmother are based. Oklahoma is home for him, but as a young man he left the minute he could. Because he was different.

“I knew I had to get out,” he says. His family, multiple generations, attended the University of Oklahoma and were deeply entrenched in the university’s Greek system. It was considered a given that Henderson would follow suit. “You know what,” he says, “I was petrified, petrified of being in the fraternity. If I followed family tradition and went to OU, it would be expected of me. And I knew that I was different, but I actually didn't come out until I was 26.”

His father, a stereotype-eschewing man who values education, took him on a trip to visit some East Coast colleges, and though Henderson had excellent grades he wasn’t sure he’d get in. “Georgetown accepted me, and to this day, one of the scariest moments of my life was waving goodbye to my mom.” He was on his path.    

 At Georgetown he majored in international finance, but his secret dream was to be an actor. He remembers, “It's something that I had wanted since my earliest memory, but I was afraid to tell my family. It kind of coincided with being gay in many ways. I was miserable by the end of Georgetown — not with the school, but with what I was studying. So I spent my senior year auditioning for acting programs in New York City, and got waitlisted at Juilliard and got accepted into the American Academy of Dramatic Arts.”  He told his father. “I was so scared to tell my father, you know, they’d just spent all this money on my education, and I wanted to go to acting school. And he was great about it! So I went to the American Academy, a two-year program.”

The Big Apple and True Love

Henderson graduated from the American Academy of Dramatic Arts in May of 1988. And then: “I got cast in an off-Broadway play in October of 1988. And who was in that play? Joseph. My husband.” The play was “Reaching Out,” directed by the son of actor Olympia Dukakis, also the nephew of politician Michael Dukakis. But we digress. Our hero had found his leading man, but they would remain merely friends at first.

Massa, whom Henderson lovingly describes as a true artist, had grown up in New Hampshire and held a degree in theater, and in a tale as old as time, had moved to New York City with a bus ticket and a few dollars in his pocket, initially living at the YMCA. After saving enough to move in with a friend, like many working actors, Massa started looking for a day job, and was advised to try construction because it paid well. His first construction job (building cabinetry in New Jersey) led to a job in scenic construction. “He did that for many years, while also acting and directing and producing.” Massa was even a set builder for “Saturday Night Live” in the mid- and late ’80s. “He's brilliant,” Henderson says, “And modest about it.”

The pair worked together again in 1990. “We did another play; he actually wrote it. And it was off-Broadway on 42nd Street. And that's when we became a couple. We were in theater all through the ’90s. Toward the end of my theatrical career, I was doing a one-man show that he directed and produced. We literally went from city to city, not knowing where our next meal was coming from, with our set and our costumes and the props and everything in our Nissan station wagon.” The one-man show was slated to be turned into a huge production. “We had several producers and investors, but one producer wound up being a nightmare.” The couple decided they couldn’t work with him — and with that, the curtain came down on Henderson’s acting career.

Luckily, he had that fallback degree, the one in international finance. He took a job. “It was with Moody's Investors Service, which is a big, big bond rating agency. Within a year and a half, I became a vice president. It was kind of crazy time. And that enabled us to buy the cabin I’m sitting in right now right now, in the Catskills, as a little weekend getaway.” After Moody’s, he moved to a commodity derivatives risk-management firm. “I was just miserable,” he says. “Joe moved up to the Catskills and started selling real estate and I stayed in the city and was still working. We were toying around with what to do. Then 9/11 happened, and that was the final straw like it was for so many people.”

Escaping the Urban Jungle, the Fire and the Resulting Desert Epiphany

Enter Eric Wedemeyer, real estate agent and agent of change. Massa had been working for Wedemeyer’s real estate company. “He's been kind of like a mentor,” Henderson says. “He was like, ‘You know, there's this property in Roxbury, New York…’” It was a 10-unit motel but hadn’t functioned as a motel since the late ’70s; it was being used for transient housing. “He told us that the area desperately needed more lodging, so maybe we should look at that.” Wedemeyer’s advice was: “Just make it lodging. I know you guys. Don’t go crazy with it.”  

Famous last words.

The Roxbury Motel opened in 2004.  Its vibe was mid-century modern at that point. They were paying tribute, Henderson said, to the era of the classic 1950s family road trip, before Norman Bates ruined motels for everyone.

“We did one room which we thought, at the time, was over the top,” says Henderson. “It was like an experiment, and we thought it was just going to be too much for people. We called it the Austin Powers Suite. It was the only suite that had a separate bedroom and little kitchen, still does. It's now called the Shagadellic. And from day one, that's what everybody wanted.” Then, New York Magazine ran a blurb with a photo about the Austin Powers suite, which put The Roxbury Motel on the map. Bookings were growing. Its reputation grew, too.

Before long, they’d optioned a piece of land in another village with plans to franchise. “And we're talking to Hilton and Marriott … Choice Hotels, it's called.” The couple took a risk, put a second mortgage on their house and spent money on architectural plans. “But we had this nagging feeling in our gut that it was a mistake.” The behemoth corporation began doing what behemoths do: dictating design directions and forcing compromises for a potentially very lucrative lodging franchise.

Then two things happened. First, a home that the couple owned and was renting to vacationers (ahead of the Airbnb curve), beautifully furnished with Henderson’s grandparents’ furnishings, burned to the ground. “We were awakened one morning, and both of us had the same thought. We both felt like we were in New York City, because we were awakened by all the sirens. And we were like, ‘Wait a minute, we're on our mountain. Why are there sirens?’” Their windows were glowing from the inferno. The house was worse than a total loss.

“So it was one of those life-changing moments. And we were scheduled to go on the first vacation we had had in two years in two weeks.” Everyone told them just go, just go. “We also found out that because it was a second residence, it wasn't insured for replacement value and we actually wound up owing $100,000, which we didn't have them. So that's a long-winded way of saying it was if it was a screenplay, you know, that was the cathartic moment.”

They took their trip, a tour of the American Southwest, hearts broken. Henderson says, “I was driving between the Grand Canyon and Las Vegas … Joseph got very sick and wound up in the hospital for two days on our vacation, because he got pneumonia.” Massa had worked tirelessly in the smoldering rubble, trying to find things he could save. “He was in the passenger seat next to me, I was driving and I had this moment where I was like, ‘We can't build a Marriott.’”

In a made-for-Hollywood moment, they scrapped the big corporate deal, stayed true to themselves and forged their own sparkling, magnificent path. And hallelujah for that.

The Roxbury Motel got a big glow-up and an expansion, with reimagined décor in increasingly elaborate themes based on classic television shows from the 1960s. Think “I Dream of Jeannie,” “The Flintstones,” “The Partridge Family” and the like. Even more elaborately themed mansion rooms and tower cottages with 30-foot ceilings are available at the Roxbury at Stratton Falls, which launched just as the COVID-19 pandemic began.

What seemed like a huge setback, maybe even the beginning of the end, turned out to be a period of concentrated creative time that allowed Henderson and Massa to pour themselves into every detail of the Stratton Falls location. The results are stunning.

They’re total fantasy immersion, as the couple likes to say. Each room or suite is a living work of art, almost too elaborate to describe, but Henderson sums it up: “Imagine if Alice in Wonderland married Willy Wonka and set up residence in Oz. That’s what we want the Roxbury Experience to be.”