The Guardian of Sleepy Hollow Cemetery

COURTESY PHILIP ZEGARELLI ’70, SIPA’76

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estled in the picturesque village of Sleepy Hollow, N.Y., is a place where history, legend and a bit of the supernatural intertwine: Sleepy Hollow Cemetery. The 90-acre expanse, with nearly 46,000 interments, is not just a resting place but also a destination steeped in lore, thanks in part to Washington Irving’s famously terrifying tale, “The Legend of Sleepy Hollow.” Leading this historic site with a blend of reverence and practicality is cemetery president Philip Zegarelli ’70, SIPA’76.

The cemetery is especially bustling during the Halloween season, when visitors flock there to get a hit of the haunting atmosphere. In the story, the Headless Horseman rises from the Old Dutch Burying Ground, which connects to the Sleepy Hollow Cemetery and has gravestones dating to the 1600s. Irving himself is interred in the cemetery, but Zegarelli notes that it’s not been an entirely restful place for the author: “That’s actually not his original tombstone. It’s his third — because he was so popular, people chiseled away his tombstone for souvenirs.”

Zegarelli in fact hails from Sleepy Hollow; growing up, he spent his summers swimming in the Pocantico River, which gracefully bisects the cemetery’s grounds. “To me, it’s a vocation of sorts,” Zegarelli says of his role. “I feel like I’m returning something to the village.

“It sounds a little crazy,” he continues, “but the cemetery was always a part of me because we lived on the other side of the river, where the bulk of the cemetery was. I have family buried there, and a lot of my friends and their families are buried there.”

While growing up, Zegarelli never imagined he would someday be responsible for its residents’ forever home. At the College, he was a member of the NROTC and, after graduation, he was assigned to Antarctica. “It was a world apart,” Zegarelli recalls. “People thought of Antarctica as just a light bulb on a globe.”

His four years of service there were transformative, he says. He supported the National Science Foundation’s research efforts and engaged with scientists, making frequent trips between New Zealand and the frozen continent. (Even now Zegarelli remains active in Antarctic affairs as director of the Old Antarctica Explorers Association, which advocates for the continent’s preservation as a natural and unclaimed sanctuary.)

Once Zegarelli returned to more temperate climes he pursued a career in banking, specializing in loan workouts. In addition to his banking work, he served as mayor of Sleepy Hollow from 1979 to 1987, then again from 1999 to 2009. In 2009, he became village manager of neighboring Briarcliff Manor and held the position until 2021. He had long been on the board of the Sleepy Hollow Cemetery when fellow board members approached him to consider the presidency.

Zegarelli officially became president in March, and now faces the delicate task of managing a site that is both a historic landmark and a tourist attraction; the job requires a unique blend of sensitivity and savvy. “It’s terrible to say it’s a business, but a lot of business acumen, knowledge and experience are perfect for running something like a cemetery,” he says. The cemetery operates as a 501(c)(3) corporation, which helps fund the necessary repairs and maintenance. “There’s a real story to tell here,” he says of the cemetery, despite its spooky fame. “It’s beautiful, scenic, well laid out. It’s a place to spend some time just walking through unencumbered, enjoying a truly quiet place.”

The cemetery hosts many events for visitors, including nighttime tours illuminated by lanterns and candlelight, a murder-themed tour that details some of the shocking final tales of the cemetery’s residents and walks that take visitors to the graves of the famous. For all the ghostly fun that happens on Halloween, Zegarelli is clear that the cemetery is a year-round place of importance to the town and to him.

“I enjoy what I do,” he says. “We have an obligation to the people who have chosen to be interred here. And this may sound a little hokey or a little spooky, but we have the responsibility for taking care of their bodily remains — whatever form they may be in — for eternity.”