Harry’s next act: Water St. Market developer revels in new stage of his career

Architect, actor and real estate developer Harry Lipstein

Harry Lipstein discovered theater late in life. His first audition – eight years ago – required an English accent and at least a modicum of theatrical experience. He had neither. Didn’t know stage right from stage left. Hadn’t even read the script beforehand. Nevertheless, against all odds and his every expectation, Lipstein got the lead in a regional theater production of Alan Ayckbourn’s The Norman Conquests.

Lipstein still seems stunned by what happened. It’s a quality that persists when he talks about the unlikely road that, more than 20 years ago, led him to create New Paltz’s popular Water Street Market. His more recent addition to the village’s cultural life is Denizen Theatre, the sleek black-box theater that he designed, which sits unobtrusively behind Water Street’s folksier small-shop façades. Water Street is his all-but-grown-up first child: well-established, respectable, popular. Denizen is his new baby: needier than its sibling, more demanding, more surprising. Guess which one Lipstein’s crazier about.

Lipstein grew up poor in Queens, the son of a cop and a barmaid. “Our family life was more like Jerry Springer – and not in a bad way,” he begins to explain over coffee last week. “My dad, at age 45, who had a wife and two kids, leaves them, never to see them again, meets my mom, who’s a Greek single mom – at the bar, of course…”


Stability was not part of Lipstein’s upbringing. Nor was the need for a formal education. None of his siblings made it past high school. This was not going to be Lipstein’s fate.

One day in his senior year, his mother sat him down and began paging through a book of career possibilities. They didn’t get far before his mother’s eye fell on a career description that, the book said, required little more than math skills. “And you could make a lot of money,” Lipstein remembers. Thus was Harry Lipstein launched on a career as an architect.

He made a powerful impression when he arrived at Syracuse University in the ’80s, following two years of study at City University. His silk shirt, rings, gold chains, bracelets and accent all screamed “John Travolta” to his bemused, penny-loafered, L. L. Beaned fellow collegians. Lipstein wasted no time adapted to SU’s comparably bucolic setting. To this day, you’ll not find so much as a wedding ring on his person. The last vestiges of Tony Manero’s Brooklyn accent went the way of the snow in a Syracuse spring.

After graduating with a five-year degree in Architecture, Lipstein scraped up enough money to buy and rehabilitate a couple of run-down stone houses in Orange County. He was successful enough at it that, when he saw a request for proposals on a dilapidated property at the bottom of Main Street, he was ready with an idea and a considerable bank loan. The idea cost nothing. The loan was for $1.8 million.

His voice colors with disbelief at the memory of what he did: “I can hardly believe I was foolish enough to have asked for that much, or that the bank was foolish enough to give it to me.” Money in hand, Lipstein designed, with Chuck Silver, what he calls a European-style, pedestrian-only walkway lined with mom-and-pop shops operated by real Moms and Pops: what many villagers and visitors consider the community’s village square.

At Water Street, there is room to stroll, outside tables and chairs, tidy restrooms and, thanks to Theresa Fall, great public events, be they vintage movies or musical performances. There’s also the chance to watch the sun go down over the Ridge, walk your dog or chase your child without fear of vehicular mishap. In short, Market Street is an island of serenity in a burbling stream of business-as-usual.

Denizen, the new kid on the block, began life about eight years ago in Ridgefield, Connecticut, where Lipstein and his wife Wendy were living. Wendy spotted a newspaper listing of an introductory theater workshop. “You should try this out,” she told him. Lipstein rolls his eyes at the memory. “Why would I want to do that?” He’d never acted in his life. Wendy persisted. Knowing, he says, that at some level she knew him better than he knew himself, he checked it out.

His resistance held for a couple of classes, until he discovered that acting held something unsuspected for him: a way to see himself in new ways. If he was unusually successful for a neophyte – with major roles in revivals like 12 Angry Men and David Mamet’s Oleanna, the psychological understanding that came with the effort to be emotionally truthful as a performer and as a person is what finally made a believer of Lipstein and brought Denizen into being. And because Denizen is a particular sort of theater, it brought Lipstein’s experience as an architect full circle.

Denizen is what’s known as a black-box theater, which both describes the theater space (small, austere, painted black) and defines what happens within it (you’ll never see Hello Dolly staged there). This is where Lipstein’s passion for his new project becomes most evident. He borrows a reporter’s pen and notebook to sketch out the three seating and staging arrangements that will be define the theater’s three very different and very contemporary productions. The spareness of a black box favors intimate, small-scale productions like Denizen’s first, just-ended production, Cal in Camo, in which three characters wrestled with the distilled dysfunctions of family life.

Denizen’s next production, Adaptive Radiation, which opens on December 6, is being billed as an alternative comedy featuring four millennials catapulted into a whimsical new world where their assumptions about adulthood, career and education are challenged in the face of a darkening reality. Lipstein calls the company’s third production, The Arsonists, a redemptive tale inspired by Sophocles’ Electra, in which a father and daughter, on the run from the law, must learn to let go.

Lipstein looks up apologetically from his seating sketch, says that he gets carried away sometimes. Theater does that to him. It’s not an intellectual process for him. It’s not easily explained, but he gives it a shot: “What I’ve learned [through theater] is we’ve all got these personas: father, husband, daughter. But we spend very little time with the truth. And the only way to affect your audience is to be in the truth. If you’re onstage and that character is coming from the heart, you’re really not acting; you’re giving a piece of yourself. And when an audience sees that, they’re affected to the core.”

Live theater, he said, can be subversive in a powerful and positive way. People enter a theater hoping merely to be entertained. But if a truthful moment happens, if the connection is made between what and who is onstage, people leave the theater feeling more empathetic, less encumbered by those personas, than when they entered. It’s moments like those that Lipstein lives for these days – moments that he hopes to share with the community he has helped to create in the big black box at the bottom of Main Street.

The world premiere of Hannah Benitez’s Adaptive Radiation will preview December 6 and run through to December 30. The regional premiere of Jacqueline Goldfinger’s The Arsonists will preview on January 31 and run though February 24. For further information, call (845) 303-4136, e-mail information@denizentheatre.com or visit www.denizentheatre.com/tickets.

Adaptive Radiation, December 6-30, Wednesdays-Saturdays 8 p.m., Sundays plus Saturday, December 8, 2 p.m., $24/$20/$15/$5, Denizen Theatre, Water Street Market, 10 Main Street, New Paltz; (845) 303-4136, information@denizentheatre.com, www.denizentheatre.com/tickets.