“I’m really very boring,” Terry Regan says of being the subject of this profile. It’s 7:30 on a Saturday morning when I arrive at her house. Between running Labrador field trials on her property (they didn’t exist anywhere in the area, so she built a program herself), golf lessons (a new sport she’s picked up this year) and a litany of other appointments, this is the only time she’s got; the sure sign of a boring person, right? She’s alerted me the house is a mile up the road. There’s a sign about half a mile up that says, “Keep Going;” then another, “Almost There...” Only later do I realize they are harbingers of our interview.Terry and her husband, John, moved to Millbrook in 1985 from Montauk, Long Island. John, who was born in Ireland, grew up in East Hampton, while Terry, a native Californian, was a top Grand-Prix amateur rider training under Olympian Anne Kursinski. “When I saw the Hampton Jitney on the back roads, I said: “‘Darling, it’s time to go,’” she recalls. The couple visited Cynthia Cogswell for July 4th weekend and two weeks later they rented Thimble House, a small cottage on Fraleigh Hill Road. “I’ve lived all over the country: Palm Beach, Laguna Beach, Northern California, Colorado, Idaho, Nantucket; the most beautiful places in the country. When we came here, I thought: “Oh, my gosh. This is where I want to live.” It was the horse country that originally sold the couple on the area (these days her life “has gone to the dogs,” as she puts it), but some thirty-five years later, the Regans have never left Fraleigh Hill Road.
The facts of the Regans’ history on Fraleigh Hill Road line-up this way: Terry’s mother followed the couple to the area and bought 300 acres from Leslie Barclay, one of the Dutchess Land Conservancy’s founders. The transaction marked the first sale of a DLC-protected property at the genesis of the organization. She built a large white house, while
Terry and John continued to rent Thimble House. When Terry’s mother died in 1996, the couple moved into her house with the intention of selling it, which they did, along with half of the land. Terry and John kept the remaining 150 acres, where they built their current home, notably from wood and stone harvested from their own land. But the romance of this story begins earlier: “We would drive by this property and there wasn’t anything but the barns. I kept saying, ‘This property is so beautiful. Boy, it’s beautiful,” she remembers. “One day, I knocked on the front door. I’m such a dork,” she asides. “And I said, ‘Hi, my name is Terry, and my husband and I just moved here. I love your property. If you would ever sell it...’ And [Leslie] said, “Oh darling, that’s lovely. I’ll never sell it, but I’ll keep that in mind.’’ Sure enough, six months later, Leslie approached John at a cocktail party while Terry was down in Wellington with the horses to ask if the couple was interested in buying the property. Some things, as they say, are meant to be.
Terry’s involvement with the Dutchess Land Conservancy began when Nancy Hathaway asked her to chair a luncheon in 1998.
“Back then, there were only 75 people or so. The events were teeny,” she says. For the next six years, Terry co-chaired an event or lunch or both, working side-by-side with caterers and vendors. Again and again, for more than twenty years, Terry rallied the community to come together behind the mission of the DLC, including developing the lunch at the Millbrook Horse Trials as a fundraiser. In 2000, she joined the Executive Committee and served for 10 years, rejoining in 2017. “I am so honored to be a part of the DLC. When people come up here to work with the dogs, they are always so astounded at how beautiful the area is. I say, ‘Take a look around. This is all thanks to the DLC.’ It is such an important organization.”
At the beginning of 2020, the DLC’s event calendar was going to be no different than any year; if anything, it was set to be a banner season honoring the 35th anniversary. While the Spring Barn Dance was scratched due to the COVID-19 outbreak, there remained hope that the Fall Country Luncheon would be able to go on uninterrupted. The Regans were set to host the event at Fraleigh Hill Road. Perrin Martin and Michael Poulin agreed to co-chair. Leslie Barclay was returning with fanfare. In the end, the decision was made not to go forward, but Terry remains undeterred. “Thirty-five is only a number. We’re going to celebrate the anniversary next year here and it’s going to be a great event.” I can’t help but think of the signs on her driveway: “Keep Going.” “Almost there...” Indeed, we will keep going and hopefully, we are almost there. And the celebrations— when we get there—will be even bigger, better and more fun than ever before and I can’t think of a better lady to help get us there, on the top of Fraleigh Hill Road. 
