Dover artist Winifred Way’s favorite subjects are people around town

Daniel Larlham Jr.Culture, Headlines

a man wearing glasses and smiling at the camera

Dover artist Winifred Way’s favorite subject matter is people.



When you see Winifred Way at the Dover Public Library, she’s usually not searching the stacks for a book.

She’s likely sketching one of the many homeless who use the library as a temporary haven.

“They sit there, and they just fall asleep,” she said. “It’s almost like going to figure drawing class and your model is right there. It’s just like getting in the train and sitting in one of the cars in the corner around noon or 3 or 4 when it’s not rush hour, and you take your sketch pad, and you just sketch people sitting on the train.”

Way has been sketching all her life.

As a child moving from place to place because of her father’s career in the U.S. Air Force, she would draw pages from the National Geographic onto a chalk board.

It’s her first memory of creating art. 

Way’s family settled in Dover in 1965 when she was in the fourth grade. After she graduated from high school, she attended Delaware State University for a year. Then she transferred to the Art Institute of Pittsburg, where she finished her art degree.

Way says she’s adhered throughout her career to one piece of advice that she received from a professor at the Art Institute. 

“She gave me a D in my class, and I probably blinked. I don’t think I cried,” Way said. “I couldn’t understand why. She did pull me aside, and she told me, ‘Winifred, this is finished, and this is good. But if you would have the next two hours and put more effort into it, it’d have been five times better.’ I still remember that.”

What Way learned was that coming back to a painting instead of fitting it into one sitting is an important virtue. 

Way returned to Delaware after college before setting her sights on New York City in 1995. She would go on to live there for 15 years. 

“I just went in with the attitude that I was the only artist in New York,” she said.

While in New York, she would open the New York Times and look for people who in turn were looking for an artist. 


“I would cold call people,” Way says. “I would say, ‘I don’t know you; you don’t know me.‘ Not that I didn’t care. I just wasn’t scared.” 

This approach got her work with Humpty Dumpty Magazine, Poetry Magazine and McGraw Hill along with commissions from a greeting card company and publisher based in Philadelphia.

The attitude is typical of her devil-may-care approach to life, even towards the most benign events. 

Way recently went to Brecknock Part to get her cardio in. Because park attendants were clearing the trail in the morning, bees had been disturbed and Way subsequently ran right into them, receiving several stings. 

After she ran out of the wooded trail and into the open area of the park, she saw two other women running away and swatting at bees. Way laughed off the incident.

She returned to Delaware in 2010 after some convincing from family members, still determined to create her art and nothing else. That’s remained true, except for her volunteer work at the library curating art exhibits.

“Every day I’m doing something in the arts,” she said. “Mostly hand to paper. I always carry my sketch books with me. 365 days a year hand to paper.” 

The time she spends at the library gives her time to sketch her favorite subjects: people. 

Way’s approach to sketching the homeless who use the library to sleep or get away from the rain sounds like a anthropologist in the wild. She sits quietly back in the corner and usually does not disturb her subjects. 

On one occasion Way recalled going to the historic train station in Dover to sketch shadows during a particular time of day. She found a homeless man sleeping in a white sleeping bag. That random occurrence launched Way on a series of pieces featuring the man she knows as Steve. 

“He’s really a nice guy,” Way said. “And I posted it. Apparently a lot of people around the area knew who he was.” 

Way also spends time at Spence’s Bazaar, a popular farmers market in the middle of Dover, interested in the Amish who come to the Market to buy and sell foods and crafts.

On some days, Way rents out a table for $15 a day there and sits and draws patrons. She likes the plain clothes of the Amish and how sunlight hitting their features creates contrasts. 

“There’s some really good character there, too,” Way said. “My whole thing is I like to do people, so I try to go where there’s going to be people. If you try to walk downtown Dover to try and find people, there’s nobody ever outside. So that’s why one of my go-to places is Spencer’s Bazaar.” 

Contrasts between vibrant colors and shadows seem to be a staple of Way’s work, along with the frequent use of white spaces that further highlight colors and shadows. 

If she doesn’t have the time to sit down and paint something that catches her eye, she makes a mental note of it. When she finds time, she returns to the place at the exact time of day and tries to recapture the essence of what she saw.

It’s hard, she said, but she takes it as a challenge to herself. Even so, she admits that paintings she makes on a whim almost always turn out better than when she tries to recapture the scene.

“I don’t know what it is. Most of the time I’m just like ‘oh, look at that’ and I’ll just do it and it comes out good,” Way said. “But if I know and I come back and I try to do it again, it doesn’t work for me.” 

Even so, she chases some buildings and places at certain times of the day or the year to capture what originally caught her eye. 

Way said she’s been trying for five years to be at the state Supreme Court building on Dover Green to capture it when the sun hits just right.

The biggest challenge in returning to Delaware, she said, is the lack of a vibrant art scene. 

“How do you not have the arts, as big as they are, since I’ve been here and met all these people,” Way said. “The more I sketch outside — I don’t care where I am — I meet somebody that’s an artist. Something’s not making sense to me about the arts in Kent County.” 

Way would like Delaware art scene to shift a bit away from Wilmington and Rehoboth and focus more on Dover. She recalled that when she was in high school, there was a thriving Dover art scene and people would often be outside painting or drawing. 

She hopes that soon there will be a reopening of the Dover Art league, which she thinks could help boost arts in the state’s capitol. 

Way, 62, has been asked several times by the Mispillion Art league to teach classes but hasn’t because she would only want to teach a higher-level class and doesn’t think she would make a good teacher. 

Clearly comfortable with strangers and pleased to talk to new people, Way encourages other artists to talk to anyone who comes up to watch while they’re working. 

“Tell them about yourself and always have a business care you can hand out,” she said.

But mostly, she said, artists should stay true to themselves and not be afraid to look at other artists’ work.

“Still take classes, no matter what there’s something that you didn’t know or something that you forgot about,” Way said. “No matter what you do hand to paper, hand to note, hand to foot every day watch a movie, looking at someone that can teach you technique, reading a book or even just going out and just sitting and looking. Just keep looking.”

In the Art Student League in New York, Way took a watercolor course for the first time, the form of art which went on to become her staple. 

Even today, she strives to learn. 

“I’m not a big computer person, but YouTube for water colorists are off the hook, and it’s free,she said.  “I don’t have to go to Paris to see this guy do his watercolors, and I can go rewind that and watch it again.”

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