Pictured: Artist Luther Rosebaro works on a portrait of Fredd Atkins as a young man.

For Chalk Festival founder Denise Kowal, scaling back beneath the weight of COVID-19 pressures would not cut it. Already accustomed to the uphill battles of securing permits and garnering support from businesses in the Burns Court neighborhood for the annual Chalk Festival weekend, Kowal has learned to overcome obstacles with creativity and effort. Last year’s 3D illusion installation in the former Ice House opened amidst the tense uncertainty of the early pandemic wave, and this year, she helped put together an outdoor walking exhibition to celebrate Sarasota’s centennial.

Called “Avenue of Art,” the walking exhibition includes over 150 paintings across four blocks of sidewalks on S Pineapple Avenue and Orange Avenue. The artists, ranging from Chalk Festival regulars to children as young as two, all share the common through line of depicting the iconography and history of Sarasota. Portraits of early Sarasota socialites like Bertha Palmer share the sidewalk with sunset scenes, lifeguard stands and circus animals. But for Kowal, the deep dive into the history of the region yielded revelations in subject matter for herself and, she hopes, for visitors.

“I didn’t know about our rich golf history and I learned a lot about our flora and fauna,” she says, “but it was really eye opening to learn more about Sarasota’s Black history.” Artists Luther Rosebaro and Lori Escalera both found rich subject matter in the city’s earliest Black settlers. Rosebaro did portraits of Dorothy Smith, Leonard Reid, Fredd Atkins and other prominent Black figures who helped to ensure the prosperity and equality of the city’s Black residents. Meanwhile, Escalera painted colorful portraits of Emma Booker and Lewis and Irene Colson. “It’s interesting that if you were a wealthy white settler, there’re plenty of pictures,” says Kowal, “but if you’re trying to find a picture of Emma Booker, good luck.”

The history would become an integral part of the exhibition, with QR codes on each painting directing viewers to a comprehensive description of the historic figure as well as a bio of the artist. “I just felt that if the history was that new and interesting to me, other people would be interested too,” says Kowal. That extra effort helped the scope of the exhibition balloon out to the size of the usual weekend-long chalk festivals despite the seemingly reduced and unobtrusive footprint.  

“Every event has its own challenges, and this was no different,” says Kowal. The sheer number of artists, the broad array of skill levels, the deep dive into the city’s history, a website with entries for almost every painting—all of it meant more legwork for Kowal to orchestrate all the moving parts. But, as the Delta variant continues to spread and raise the hackles of arts organizations, she hopes the outdoor exhibition offers locals a fun, interesting and, most importantly, safe way to learn about the city and experience beautiful art.

Pictured: Artist Luther Rosebaro works on a portrait of Fredd Atkins as a young man.