As Cynthia Woodyard likes to tell the story, she “married” her garden. 

The affair began in 1972, when she moved with her then-husband into a ’20s-era Arts & Crafts bricker in Sylvan Heights, built with a picturesque flair by an English contractor and his Scottish wife. Woodyard liked the lot: it had five sides, none of them parallel. 

Early flirtations included an herb garden, and then some vegetables. The relationship evolved. Woodyard put up a fence and, with her father and brothers, rebuilt a tattered greenhouse once occupied by a giant lilac. She tried her hand at perennials and, one day, put some out in a garage sale. Buyers snapped them up. Within a couple of years, Woodyard had lines down the block from her garage for an annual sale of hostas, astors, irises, and campanulas. 

She and her husband divorced in 1988. Her horticultural soul mate became a passport.

“[The garden] was my freedom,” Woodyard says, recalling how she once made $11,000 from one three-day sale. Her talent with perennials earned her landscape design jobs with Portland’s elite families and funded travel abroad to learn more. The lessons, in turn, took root at home in her own three-quarter-acre phantasmagoria. 

No xeriscaping here. Think English Victorian meets early Walt Disney; Edward Scissorhands snipping a topiary bubble bath to a French pop beat. Woodyard is fearless, freely mingling the sturdiest hardy plants with delicate exotics. (Many spend winter in a heated garage.) The density of her contrasts—spiky and soft, espaliered, climbing, and upright, green upon green upon green—attests to plenty of long mornings and evenings with the soaker hose. “Any real gardener only hand-waters,” she says. “You get to know the plant, what it needs, what’s eating it.” 

“The textures, the shapes, the juxtaposition of formal and informal plants—not everyone can do that, but she sure can,” says esteemed local landscape architect and garden historian Wallace K. Huntington. “Cynthia can grow hostas like no one in the slug belt. There’s not a chewed leaf. And she handles boxwood better than anyone I’ve ever seen. She uses it so imaginatively that there isn’t any longer a memory of ancient pictorial gardens.”

And then there is her humor. Woodyard likes balls: boxwood orbs rising against the blooms like pom-poms, drifting through the green like glass floats, or clustering around a granite globe like it was the cue ball on a crowded pool table. Against the bending mortar lines of her brick outdoor fireplace, Woodyard prefers brightly colored Philippe Starck chairs and, on her porch, a classic Marilyn lip-shaped love seat. The curving paths through the garden’s pentagonal shape make the three-quarter acre feel infinite—getting lost in Woodyard’s garden fantasy is easy. There is nothing quite like it in Portland.

Small wonder. Woodyard’s early self-taught mastery soon took her around the world, forging connections with some of its greatest gardeners and allowing her to broaden her repertoire far beyond the Pacific Northwest’s usual palette of rhodies and roses. A 1980s Sunset magazine article on her garden earned an invitation from the editor to do a “process story” on dividing perennials. So she picked up a camera for the first time and quickly learned that her natural flair with plants translated to pictures, and in turn, photography assignments from Horticulture, Better Homes & Gardens, and Organic Gardening, among others. She’s contributed to a shelf of books: The Complete Kitchen Garden, The Garden in Autumn, Gardening with Ground Cover and Vines, Annuals, The Inviting Garden, and Secret Gardens: Revealed by Their Owners (the last two featuring Woodyard’s own garden) written by or featuring gardens by a generation of master gardeners now past, from Princess Greta Sturdza to prolific English garden designer Rosemary Verey. Woodyard gleaned lessons about both horticulture and life. (Verey, she says, “taught me how to drink.”) She also brought back plants from her travels: “Back then,” she recalls, “you could still smuggle.”

Now 71, Woodyard’s most recent influence evolved out of her 13-year mentorship of Francisco Puentes, whom she first met on the crew of one of her contractors. Now 32 and a sculpture major at Portland State University, Puentes recalls how his first encounters with Woodyard and her garden opened up a world. “I could just tell that I could progress in the realm of plants,” he says. “I felt a strong desire.” He quickly became her right hand in tending the garden—today, the two gardeners finish each other’s sentences. “I can prune, but not like him,” Woodyard says. “He has good ideas. The design is going more and more his way. It is simplifying.” 

Puentes has also expanded the garden’s giddy freedom. Using welded-wire cages, mesh, soil, and ornamental grasses, he invented what he simply calls “columns” that stand like a family of odd sentries at the gate. His tiny lighted “nests,” spun out of sisal, hang like glowing cocoons in the trees. 

Working every evening for nearly a year, Puentes wrapped a woven steel armature with wire to create a life-size elephant. Knees seemingly cocked to launch into a dance—or maybe a charge—the rusted-red giant has the visual strength of a basket but the dynamism of a fast line-drawing. The inspiration? He recalls his first trip to the Oregon Zoo and the instant affinity he, as a fellow immigrant, felt toward the elephants. Puentes is now at work on “a baby,” he says. “Maybe one day a whole family.”

Woodyard’s mentor Verey, who edited the 1994 book Secret Gardens: Revealed by Their Owners, titled the chapter on Woodyard’s garden “A Paradise From Many Lands.” Yet, in it, Woodyard muses less on her global reach than her love of boundaries and the garden’s daily drama of plants, insects, and weather. “Here was a little piece of land,” she says. “Season after season. Nature. Working is what happens. It’s been a long experiment, you have to admit, in one place.”

woodyard’s plant picks

1. Mood Indigo, Agapanthus inapertus: “Hardy, sexy, dangling.”

2. Veitch’s Blue, Echinops ritro: “It’s dependable, blue, and bees love it. Stands on its own and is fairly drought tolerant.”

3. Fire Lily, Clivia miniata: “Not hardy, but easy to keep over the winter—very sturdy green leaves, good bloomer, floriferous and orange, red seed pods.”

4. Francisco Puentes tiny lighted “nests,” spun out of sisal, hang like glowing cocoons in the trees. 

5. Nymansay, Eucryphia x nymansensis: “A small, woody tree with a dogwood-like flower.”

6. Kangaroo Paw, Anigozanthos: “Totally tropical. Reminds me of Australia.”

7. The Swan, Hydrangea paniculata: “Very unusual, big pure-white flowers, yet loose white flower heads. Very sturdy. Nothing eats it.”