Fifteen years after she graduated from Columbia, Anna Stark was in the South Loop near the farmer’s market she used to go to when she lived in a nearby dorm.

But now she was interacting with customers, sharing laughs, connecting over childhood memories and selling them all kinds of artwork from small and medium-sized oil paintings to stickers of crumpled soda cans. 

“I couldn’t stop smiling yesterday, and I can’t stop smiling today,” said Stark, who is from the Minneapolis–Saint Paul metropolitan area of Minnesota.

Stark was one of 95 artists who packed the 700-block of South Dearborn Street for the kick off of the Printer’s Row Art Fest near campus. 

The first day of the Printer’s Row Art Fest was on Aug. 10, with passersby browsing booths lined with painted canvases, clothes and other artful trinkets. 

The free weekend event took place around 701 S. Dearborn St., stretching from the block of West Harrison Street and South Dearborn Street to West Polk Street. 

The block was packed with artwork, tables and tents of food vendors, face painting, a kids art zone, and live music on two stages that were placed on the north and south entrances.

Stark’s tented booth was covered in oil paintings of colorful florals, games, candies and sodas. She also had a display of prints, magnets, keychains and stickers that whooshed out to the walking path like confetti anytime a gust of wind would pass.

“One of my main subjects is [nostalgia], finding subjects that will pull on the heartstrings of everyone,” Stark said. “I love building those connections from decades ago.”

The Printer’s Row Art Fest is Stark’s first art festival outside of Minnesota. She has been in the Uptown Art Fair and the Stone Arch Bridge Festival, both in Minneapolis, and about 10 more art fairs in the Twin Cities area.

Stark said she has gotten familiar with people who have stopped by her booth at the art fairs in Minnesota, so Chicago feels like a “brand new territory.” She’s excited to share her art with new people, having already felt connected to Chicago through living in the city and going to Columbia.

She described the energy of the Printer’s Row Art Fest as “vibrant”.

“The energy here is unlike any of the art fairs I’ve ever been in,” she said. “I just want to pinch myself, I can’t believe this. My life is just really full circle.”

When Stark attended the college, she initially majored in photography, then switched to fiction writing, ultimately landing on marketing with a minor in public relations. 

With her degree in marketing, Stark got a job working in fundraising for the National Multiple Sclerosis Society, a nonprofit organization.

“I’ll never forget my nonprofit classes at Columbia,” she said. “We had to put together our own fundraiser, and I fell in love with that.” 

“So I’ve got these different interests and loves, and I do both of them at the same time.”

During all her time at Columbia, Stark had only taken one drawing class. She recalled being happy in the class, wandering around Chicago and sketching everything she could. “If I was just listening a little bit more, I think I would have majored in fine art.” 

She wishes she could connect with her drawing teacher to tell her: “I took this one class, just one semester, but I still have all my drawings from that class, and it was definitely a seed for where I’ve taken things today, the love was there deeply.”

Stark said she started painting when she was about 28 years old with her daughter and a set of paints from Target. 

“It just started snowballing into me starting to teach myself how to paint,” she said. “Over the last four years, with thousands of hours, I taught myself, from watercolors to acrylics and now to oil painting. It’s been a long, long journey of just self-teaching.”

She describes her style as photorealism, with influences such as CJ Hendry and Erin Hanson. 

She also said her story of being self-taught serves as an inspiration to herself as well, quoting Leslie Knope from Parks and Recreation: “I am big enough to admit I am often inspired by myself.”

According to Stark, her journey of developing her art style was very natural, taking time to learn and practice drawing and using different kinds of paints. She started painting things around the house like fruits, then candy bars and paper bags. 

She said one painting will inspire the next, and her running theme has become nostalgia – trolls, Furbies, Pez dispensers and other “little childhood things”. 

“The past and just those fun things, but a lot of people kind of forget, and then it’s really fun to see their reaction, like ‘oh my gosh, I remember this! I had 20 of these when I was four!’”

Isabel Morales, a resident of the South Loop working in media relations, was browsing through Stark’s stickers and gummy bear keychains. She noticed the Surge soda stickers, which reminded her of the 90s.

“It’s kind of like when you’re hanging out either at a friend’s basement or when you’re doing a sleepover, you just have your sodas and candy – it was very nostalgic,” Morales said.

Stark said she is also getting into painting present day items “that everyone can identify and everyone might have a shared memory with.” 

Summer Bialek, a student at Seattle Pacific University from the north suburbs of Chicago, said, “She has La Croix-themed art! I’ve never seen that before.” 

Bialek also mentioned how Stark had all the best flavors of La Croix painted, bonding with her friend Matthew Eshaya, a student at DePaul University also from the north suburbs, about the limoncello flavor – both their favorite. 

Eshaya also enjoyed how many different types of art Stark was selling. “It’s nice to have a lot of things,” he said. “If I don’t have 20 dollars to spend on a piece of art, I can spend five dollars getting a little sticker or something so that I still have it.”

Stark often referred to herself as a late bloomer, having later grown her passion for art and bringing herself out of her shell.

“The whole experience, the school, the city, the students, the teachers, gave me this confidence that I definitely didn’t think I had before I got there, and then leaving there, I felt like a completely different person,” she said. “I left my heart there, but I came home with confidence.” 

Stark recounts one of her first days at Columbia where she participated in a meetup of writers where anyone was able to get up and read anything they wanted. She said she wasn’t the kind of person to speak publicly. “Something about the energy of the students and the teachers and how everyone was so welcoming, and just something about it inspired me, I was the first one to stand up,” she said. 

“The things I studied in, the professors that I got to work with, were just so inspiring. And I know that’s in my work, and it’s in everything that I do and who I’ve become today,” Stark said. “From seed to flower, that’s what it feels like. My heart’s just bursting.”

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