Although the name “Monica Aguilar” may sound unfamiliar to most Greenfield residents, chances are they have spotted her footprints on windows around the city. Her “trail” is made of paint: a snowman reading in a rocking chair at the Greenfield Public Library, Snoopy smiling at Brad’s Place, a penguin lifting weights at Franklin County’s YMCA or, most recently, an ogre, raccoon, bumblebee and mermaid playing a board game at Greenfield Games.
Aguilar, who grew up in Millis and now resides in Barre, has painted about 30 windows along the streets of Greenfield’s downtown, leaving behind a gallery of penguins, gingerbread men, skiers, raccoon cupids and other characters. Although most of these scenes came from her Jingle Fest commissions, she expects future gigs in Greenfield as word about her art spreads.
And when an artist is painting windows on Main Street instead of a canvas in the solitude of a studio, word spreads.
“There’s a lot of workplace satisfaction, because no one’s thanking your plumber for fixing your toilet, but almost everyone will walk by and be like, ‘Oh my god, that’s so cool, that’s really beautiful, thanks for beautifying our town,” Aguilar said.
While the occasional joke from curious viewers passing by may throw her out of the zone as a “literal or very serious” person, Aguilar said chatting with the live audience of her art is part of the job.
“People are very kind and happy to see what’s happening,” the muralist said.
But the process behind her characters and scenes is not always pretty.
To cover the large canvas, the artist often spends eight hours a day standing on pavement, leading to sore muscles on the drive home to Barre. In the zone, she often forgets to eat and take breaks, a habit she is trying to overcome. Plus, the paintbrush strokes lead to “a little bit of carpal tunnel every once in a while,” Aguilar said with a grin.
Stretched over several hours, the paintings take more than a second to come together.
“Once I have it outlined, you just start painting, and there’s a lot of ugly stages to it,” Aguilar said.
She described the several stages of painting a mural: outlining, colorblocking “and slowly getting more and more detailed as you go.”
When confused business owners peek at the progress early and ask, “Are you going to add a bit more?” Aguilar responds with, “Yeah, don’t worry, it’s going to look ugly for 90% of it, and then the last 10% makes it look really pretty,” she said, chuckling.
Although Aguilar, 30, has created art since middle school, her career goals clung to becoming an agriculture teacher for many years. At the University of Massachusetts Amherst, she earned a degree in agricultural education and environmental science.
Then, she hiked the Appalachian Trail.
“In college, I was working full-time and a student and I was in a club, and so I was just doing everything. I didn’t have free time,” Aguilar recalled. “When you’re out on the trail, you’re walking all day — that’s your full-time job — but you have a lot of time to think about what you could be doing, and I think it made me want to get back into painting and art and realizing that I didn’t want to just be on a two-week vacation grind.”
Without distractions and duties, the nearly 2,000 miles of walking cleared Aguilar’s head. She decided to ditch the 9-to-5 plan and pick up her paintbrush.
“At the beginning, I tried throwing everything at the wall to see what [stuck],” the artist recalled.
She sold art prints, but found the cost of the materials not worth the investment when prints often went unsold. To make ends meet, she even lived in her van.
Two years after the Appalachian Trail, she started pitching murals to businesses, and something finally stuck.
Now, she balances painting the windows and walls of stores, home offices, Airbnbs and other projects with working shifts at UMass Transit Services’ maintenance department. Her schedule leaves plenty of time for more hikes.
From the Appalachian Trail to the West Highland Way across the ocean in Scotland, Aguilar has backpacked approximately 10,000 miles in total. Her arms preserve these feats with tattoos of plants she encountered on her adventures: mountain-laurel from the Appalachian Trail, manzanita from the Pacific Crest and sagebrush from the Continental Divide.
While the quiet of hiking is often calming for her, she said the moments that go wrong when there is no turning back can become the highlights.
“Some really magical things can happen when you’re outside and it’s not ideal conditions,” Aguilar said.
When it rains and the water can damage a pair of earbuds, “you just have to be in your own thoughts,” she said. “Sometimes it’s fun to just be like, ‘Well, this sucks, but I’m just going to be in this mud puddle for five miles, and it’ll be a good story later.'”
When Aguilar and her partner had to hitchhike from Denver to Wyoming, they caught a ride from a woman they quickly befriended.
“Something that could have been a slog trying to travel somewhere ended up being a really great opportunity to meet someone,” Aguilar said.
In her backpack, she packs a watercolor set for her treks.
“Being on these hikes, you see certain things that you’re like, ‘Wow, that’s so pretty, I just want to capture it,” the artist said. “I’m very protective of my trail sketches, I try to keep those to myself.”
Strokes of lilac invigorate the flowers and sky of Aguilar’s painting inspired by a campsite on the Continental Divide Trail. Mushrooms peek out from midnight blues and moss in a quick watercolor sketch.
Aguilar’s art tends to bend towards nature and wildlife — visual capsules of her travels. Within clients’ wishes for murals, her love for landscapes often peeks through, like the silhouettes of leafy plants behind the Boston skyline of her mural for Neiman Marcus.
With walls as her canvas, Aguilar said she often feels more freedom when painting a mural than a standard print and enjoys the “challenge” of filling a large space with her and her clients’ ideas.
But the muralist is committed to creating art off the clock, sketching campsite scenes and following challenges, such as creating one block print a day.
“When you’re doing this as work, you tend to just do it for other people and forget to do it for yourself,” she said.








