Middleboro’s Beloved Window Artist Is Moving On to a New Canvas

There’s a window above Center Street in Middleboro that has become famous in recent years for the bright and pleasant paintings that grace its glass.

They are the work of the apartment’s resident, Brittany Wilson, who has become a bit of a folk hero in town for her artwork and for her positive messages she brings to the community.

Although the townspeople were recently saddened by the news that Wilson will no longer be painting up her big window, it’s for the best of reasons: after nine years of living in the apartment above the shops, Wilson has purchased her own home in Lakeville.

“I’m going to miss it so much,” Wilson said of the window. “It breaks my heart. I actually cried after I finished the last window. It’s emotional, because it’s been such a great outlet for me through the years.”

Moving to Middleboro and Discovering Her "Canvas"

Wilson moved to Middleboro from Washington State.

“I kind of moved here on a whim. All my family is in New England,” she said. “I’d been out in Alaska and Washington State for four or five years, and I really wanted to move closer to home.”

She said she told her ex to “pick a state, any state, as long as it’s in New England,” and they settled on Massachusetts. Wilson grew up in New Hampshire, but her best friend lives in Middleboro.

“We camped our way across the country in a Volvo, and when we got here, we found this apartment within a week,” she said. “I thought we’d be here three to six months before we moved again, but he left after six months to go back to Washington, and I stayed because I loved it. It’s so bright, and having the window just made it so much fun.”

Wilson said the decision to start painting the window was two-fold.

“It’s kind of this huge canvas, and I felt like I should do something with it,” she said. “But also, as you’re coming down Center Street, you can see everything in my apartment through it. So painting it was kind of a privacy screen as well.”

She began by painting a jack-o’-lantern in the window in the Fall of 2014, and it just took off from there.

“I tried to do it a few times a year – Halloween, Christmas, and spring were my most consistent ones. I tried to fit others in between,” she said. “I wish I did it more often, but it would get really hot behind the window, like a greenhouse, and cleaning the window was a pain in the butt.”

You can see a gallery of her window paintings below.

Becoming a Center Street Sensation

Wilson said she always appreciated the response she got from people down on the street.

“There were a few windows where I had people that kind of hung outside while I was painting them,” she said. “People would walk by, wave hello, give me a thumbs up, beep the horn. It was a fun way to interact with the community that I really didn’t expect when I started doing it.”

Working at Coffee Milano just down Center Street, people began to know Wilson as the person who painted her apartment window.

“Then it became expected of me,” she said. “People would ask me when I was going to change it, and I’d ask them for ideas, because I was running out and I didn’t want to do the same idea twice. That became a challenge, doing something that was different.”

She even converted her TikTok account – which previously focused on her ability to bend spoons – and used it to feature time-lapse videos of her creating her window paintings.

“I was just curious as to what it would look like, which is why I did the first one,” she said.

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Time to Move On

As much as she loved painting her window, Wilson said she was having some issues at the apartment and started thinking about moving.

“I kind of always looked at Zillow, but then I started to really look,” she said.

It was when she was having a conversation with a woman about mediumship when serendipity stepped in. She asked for the woman’s card in order to talk more about spiritual things, but when the woman’s husband went to get one, all he could find were her realtor cards.

“As it turned out, I needed a realtor,” she said.

Wilson then began to look at houses, but ended up zeroing in on the one she wanted right away.

“I said, ‘I want to go see this one,’ because it had an interesting yard, and I just fell in love with it,” she said. “I asked, ‘Am I crazy for wanting to buy the first house I looked at? It was just like the house I grew up in.”

“It just happened all within two weeks, from deciding to get out of there,” Wilson said. “I loved this apartment and I thought I would stay here forever, but I found the perfect place.”

Looking Forward to Lakeville

Wilson said not only is she excited for the positive vibes of her new home – she said it was built in the 1700s and is “definitely haunted” – but also for what she can do when it comes to decorating. Although it doesn’t have the same giant window, she will still be able to have an outlet for her creativity once she’s ready.

“It has a decent front lawn, and it’s right on Main Street,” she said. “I’m hoping once I get more established, I can do something really good for Halloween decoration-wise, and for Christmas. The first year, I’ve just got to feel it out.”