Ashley Wolff’s introduction to art came early. “I was always surrounded by art and drawing things,” she said. “I always knew I wanted to be an artist.”
That determination carried her from sketchbooks as a child in Middlebury to a career as a beloved children’s book author and illustrator. Wolff published her first book in 1984, and in the decades since, she has illustrated more than 55 titles. Her books have enchanted generations of young (and old) readers with their imaginative worldbuilding.
Wolff’s roots in Middlebury run deep. Her father was hired by the college in 1956 as a Professor of Economics when Wolff was just nine months old. She grew up on Chipman Hill among a community of other Middlebury College faculty families.
“It was a great place to grow up,” Wolff said. “I could walk to school, to Mary Hogan Elementary and later Middlebury Union High School.”
Wolff recalled how her family built a room onto their house dedicated entirely to creating things, which they called “the rat hole.” Cabinets lined the walls, a large table filled the center and her mother kept a sewing machine there.
“That was a room you just went in to do stuff,” Wolff said, describing how her parents printed their own Christmas cards and illustrated programs for the Middlebury Community Players. “What you grow up with is what you consider normal. And if people being artists all around you is normal, then why not?”
Wolff describes art as being part of her DNA, in a literal sense. Her grandfather, Dr. Paul Wolff, was a renowned German photographer known for his still images during Nazi Germany and for pioneering early color photography. “It’s interesting to look back at his work and see we had similar preoccupations as artists,” she said.
Wolff went on to study at the Rhode Island School of Design, taking courses in printmaking, painting, life drawing and woodworking. From there, she launched her career as an artist, being freelance ever since.
Much of her storytelling draws from the world she grew up in, one filled with nature, animals and the freedom to imagine. Her children's books often include animals as the main protagonists that young readers can instantly recognize. Some of her notable titles include “When Lucy Goes Out Walking,” “Baby Beluga” and “Each Living Thing.”
“Being with animals was always a part of my childhood, so I naturally included them in my books,” Wolff said. “In picture books, the words don’t have to do all the work, words can set the scene, and then the pictures create the universe — they show who the characters are, what the weather is, what time period we’re in. There are so many choices to be made.”
Wolff also finds inspiration for her stories in her everyday life. One of her books, “How to Help a Pumpkin Grow,” began as a simple memory from her daily drives near Lake Dunmore, near where she lives in the town of Leicester.
“There was this lovely little farm along my route with an honor-system produce stand,” Wolff said. “The man who ran it made the most beautiful displays and grew the best corn and tomatoes and radishes.”
Over time, Wolff befriended the farmer, Wayne, and even brought her son to help pick pumpkins one fall. “I realized how heavy pumpkins are — and how prickly their stems can be when they’re fresh,” she said. “I stored that memory away.”
Years later, that memory inspired the book. Its story follows a farmer, imagined as a dog, and his band of unlikely animal helpers, including a crow, goat, duck and rabbit, as they plant, tend and harvest pumpkins together. The story ends with the animals carving jack-o’-lanterns, bringing the growing season full circle.
Beyond illustrating books, Wolff also takes on commissioned work, painting everything from boats and homes to human portraits. She is a member of the Brandon Artists Guild, a local cooperative gallery that includes more than 30 artists and artisans.
In recent years, Wolff has brought her art into the digital sphere, using social media as both a gallery and a platform for activism. Her recent work often engages directly with politics, blending her signature animal imagery with bold, socially conscious messages. Pieces that still resemble her children’s illustrations now have taglines like “Proudly Antifa” and “Don’t Stop Resisting,” reflecting what she sees as the urgency of the current moment.
“I never needed to become political until the first Trump administration,” Wolff said. “For someone who makes a lot of visual things, social media is a good platform… and as the daughter of an immigrant, I can’t be quiet about that.”
Wolff also urges young people interested in pursuing art as a career to take the step.
“I would still always encourage somebody, if you want to be an artist and you're really passionate about it, and hungry for it, then, by all means, do it and figure out a way to make a living.”
Mandy Berghela '26 (she/her) is a Managing Editor.
Mandy has previously served as the Senior Local Editor, a Local Section Editor and Staff Writer. She is majoring in Political Science with a minor in History. She is the Co-President for the Southeast Asian Society and an intern with the Conflict Transformation Collaborative. Last summer, Mandy interned with U.S. Senator Kirsten Gillibrand and participated in the Bloomberg Journalism Diversity Program.
