Skip to content

MEET THE ARTIST - Jay Sullivan paints, photographs unique works of art

Winchester artist Jay Sullivan works on one of his landscape paintings. ALL PHOTOS COURTESY JAY SULLIVAN

Table of Contents

Elm Street resident Jay Sullivan has not only taken many photographs over the years, but he has digitally enhanced many of them, some to turn into more interesting pictures, but others just for fun.

Sullivan earned an MFA in painting from The School of the Museum of Fine Arts and while there, met his future husband Joe Genova. 

“Joe gave me a camera and once I started, I got great satisfaction from photography,” says Sullivan. 

He’s primarily known for dog portraits, but during COVID-19, he returned to painting. But not with oil paints he was taught in. 

“My studio is a spare bedroom and I didn’t want the smell of oils and turpentine nearby, so I switched to acrylics,” he says.

His career included working at photo labs, printing photo murals and digitally restoring photos. Eventually, he became a graphic designer.

“Joe and I travel all over,” he says. 

Probably the farthest he’s gone is Myanmar. 

Sullivan takes photos and sometimes uses them to paint landscapes. Other treks include nearby animal shelters, where he photographs dogs and cats. The shelters post them online so the animals can be adopted.

“There’s a no-kill shelter in Sudbury called Save A Dog and they had the sweetest dog from West Virginia,” he says. “They took him to a vet who discovered he was full of buckshot. It’s legal in West Virginia to shoot animals that stray onto your property.

“Then there was Otis, a huge dog that had been given up by a woman in an abusive relationship,” he continues. “She and her son went to live in a place for abuse victims that didn’t allow dogs. When they had their own home again, she came back to look for a pet. She’d assumed Otis had been adopted, but he was still there.”

Otis was given up by a woman in an abusive relationship. But his owner came back for him.

Sullivan’s travels included Tanzania, “one of the most magical places on earth,” he says. “We went off-season and our group were the only ones in the lodge. We saw elephants that stayed with us for nearly an hour.”

Sullivan’s painting after visiting Tanzania.

For fun, he created a dog calendar with Downton Abbey and movie scenes with his dog.

Readers may have seen Sullivan at a recent farmers market. 

“It was my first time,” he says, “and I expected to sell nothing, but I sold two photographs and two of my books [The Road to Forever: A Dog’s Tale, which he co-wrote with his husband]. 

Jay Sullivan at his first farmers market. WINCHESTER NEWS STAFF PHOTO/JOYCE WESTNER

“I won two photo competitions, one with animals as the subject matter and I’ve had many commissions,” he says.

But Sullivan has the misfortune to suffer with a genetic eye problem and can’t really work with photographs anymore. 

“But I decided to do one last hurrah and took portraits of my neighbors’ dogs for free,” he says. “Now my art is almost always my landscape painting, but I’ll still take photos at Save A Dog’s annual photos with Santa.”

Winchester News is a non-profit organization supported by our community. If you appreciate having local Winchester news, please donate to support our work, and subscribe to our free weekly newsletter.

Latest

Sen. Jason Lewis to host Mass. state budget 101 community conversation

Sen. Jason Lewis to host Mass. state budget 101 community conversation

The following was submitted by the Office of Sen. Jason Lewis: Sen. Jason Lewis is pleased to announce he will be convening a Community Conversation to discuss how the $60 billion+ Massachusetts state budget is drafted each year, how funding decisions are made, and how your voice can be heard.

Winchester Historical Society announces spring program series commemorating the 250th anniversary of United States

Winchester Historical Society announces spring program series commemorating the 250th anniversary of United States

The following was submitted by the Winchester Historical Society: The Winchester Historical Society is proud to announce its 2026 Spring Program Series, commemorating the 250th anniversary of the United States. This special season will feature four engaging programs that bring the Revolutionary era to life through firsthand perspectives, historical analysis,

  Subscribe