The Old Town Art Fair, which will be held Saturday and Sunday is celebrating its 75th year. (Photo by Old Town Triangle) 

What began with a group of neighbors hanging paintings on fences in their yards and evolved to become nationally recognized, the Old Town Art Fair is gearing up to celebrate its 75th anniversary in style.  

Promising to be the largest and most festive in its decades-long history, the milestone event includes a record number of participating artists, an expansion of its Garden Walk, a variety of music and culinary choices, and a Children’s Corner featuring interactive activities and entertainment.  

Organized by the Old Town Triangle Association, the Old Town Art Fair will be held (rain or shine) from 10 a.m. to 7 p.m. Saturday and 10 a.m. to 6 p.m. Sunday. The main gate is located at Lincoln and Wisconsin streets.  

“With the 75th anniversary, we’re trying to do things a bit bigger this year across the board,” said Chris Nelson, Old Town Art Fair 2025 chair. “We have a record number of artists, increased food vendors and music stages, bigger sponsorships … more draw for a wider range of visitors. It’s a family-friendly event. Everyone can find something that resonates with them.”  

Selected by a jury of professionals from a record-setting 700-plus submissions, 230 artists from across the country will be on hand, exhibiting everything from paintings, sculptures, photography and printmaking to ceramics, glass, metal, fiber and jewelry.  

“The fair is in this historic neighborhood, and the artists love coming out,” Nelson said. “It’s a great relationship. They want to help us celebrate 75 years, and the fair helps them get their stuff out there. People know the caliber of work, and they can talk and connect with the artists. We have emerging artists just getting their start, and we have some great older ones as well.” 

One of those long-time exhibitors is Chicago-based artist Chuck Meyers, who was commissioned to create this year’s official art fair poster. Titled, “Soaring Around Old Town,” the poster was created mostly from drone photography sessions throughout the Old Town neighborhood and has been displayed on the side of bus stops and other locations in the city.  

“There’s a lot of buzz around Chuck’s booth,” Nelson said. “The poster has been different things in the past, but we wanted to do something special for the 75th. It’s been a big draw and helps promote the event.”  

The fair’s Garden Walk offers visitors an opportunity to tour 57 gardens this year, including eight new locations, many of which are private and only viewable during the event. Highlights include a residence containing a coach house that survived the 1871 Great Chicago Fire, a Queen Anne-style limestone row house built in the mid-1880s, and St. Michael’s Church, reopened in 1873 after being partially destroyed during the Chicago Fire.  

“The Garden Walk gives people a peek into the secret past of the neighborhood,” Nelson said. “There are so many historic buildings that people don’t know about. That history just adds to the character of the neighborhood.”  

Live music includes an array of local singer-songwriters, jazz musicians, folk bands and mellow rockers on two stages, including Chicago Blues Hall of Famer Donna Herula and more than a dozen other performers.  

“We’re not a music fest, but the music adds to the fair,” Nelson said. “Everyone will find something they enjoy. That goes for the food as well. We’ve got a pizza oven, some world food, Mexican restaurants, Mediterranean cuisine … something for everyone.”  

The Children’s Corner features arts-related activities for kids, including face painting and arts-and-crafts tables organized by the Menomonee Club for Boys and Girls. Daily live entertainment includes a magic show, a musical act and children’s theatrical performances.  

“We want the kids to have a chance to experience art in their own way,” Nelson said. “They can do crafts, really get engaged and have some fun.”  

Admission to the Old Town Art Fair is a suggested donation of $12 (free for children).  

“All revenues go back to supporting the neighborhood, which goes back to the origins of the art fair when they wanted to support the Menomonee Club,” Nelson said. “That’s what we continue to do. We’re really proud of the work we’ve done over 75 years — not only about art but embracing the neighborhood.”  

For more information, visit www.oldtownartfair.org.