Best Sidewalk Art and Chalk Festivals in Florida

By Carlos Harrison

It's painstaking performance art, in two dimensions. Artists spend two or three days, on hands and knees, meticulously creating elaborately detailed chalk and pastel paintings on an asphalt or concrete canvas — only to have it washed away after they're done.

“At this stage, having done it so many times, it’s perfectly natural,” said St. Petersburg-based chalk artist Dee Sabean, as she carefully colored a mountainside landscape dotted with mountain goats peering regally into the distance. “That it’s going to go away means then we’ll have space to do another one. We’re very adjusted to that. At the beginning, though, I had to look over my shoulder a lot when I went home.”

And, since they have to constantly create new ones, artist Lori Escalera, of Culver City, California, joked, “It’s job security.”

It's chalk art extraordinaire, born of a centuries-old tradition, starting with a visual arts world version of wandering minstrels. In Italy in the 16th Century, artists traveled from town to town sketching their ephemeral creations in hopes that delighted spectators would toss a few coins their way. Originally, they drew, almost exclusively, images of the Virgin Mary, the “Madonna,” in Italian. That earned them the name, “Le Madonnari.”

The tradition died away as World War II ravaged the continent, only to be reborn in the 1970s, again in Italy. Then it spread.

Now, modern Madonnari gather for chalk art festivals from the state line to the tip of the Keys nearly year-round, basking in the Florida sun, and the adulation of the passersby.

“This is a you-and-me thing. That’s where the fun comes in. People get so excited when they see it,” said Sabean.

Wayne and Cheryl Renshaw fell in love with “chalking” near their Santa Clara, California, home. He’s an architect. She’s a landscape designer. Together, they travel to festivals across the country to spend as many as 20 laborious hours sketching, coloring and shading a 10-foot-by10-foot vision that they know will almost surely be gone by the time they reach their front door again. All under the watchful gaze of a steady stream of spectators.

“You have to be a little bit of an extrovert to do this,” said Wayne.

Recently, in Venice, just south of Sarasota, the couple carefully sifted through hundreds of shades, picking well-worn nubs of chalk from their overflowing toolbox to render a nearly exact, 100-square-foot replica of a photograph that felt like something of a barbershop mirror – of art reflecting life, reflecting art:

It was an image of Wayne, photographed as he was photographing a lemur at the San Jose zoo, with the lemur reflected in the glass of the camera lens.

Would they be sad when it was cleaned away?

“No,” Cheryl said. “It’s like if you go to a play – at the end of the play you clap and you go.”

There are chalk art festivals nearly every weekend of the year in Florida. Sometimes two or three at a time. The Florida Chalk Artists Association has a good listing of events around the state at http://www.floridachalkartists.org/events.php, so you can find one near you.

Florida's West Coast Chalk Festivals

On the west coast, Venice, Clearwater Beach, and Safety Harbor all host chalk festivals at different times of the year.

Safety Harbor’s Bloom N Chalk Fest (http://www.bloomnchalkfest.com) kicks off in March with music, goodies, and artists getting an early start on a Friday evening, and ends on Sunday when competition winners are announced.

The international Sarasota Chalk Festival in Venice included a Guiness Record-setting painting in 2014, and attracted so many artists that it needed multiple venues to fit them all in. All were within easy – and enjoyable – walking distance of each other. For the most up-to-date information, visit http://chalkfestival.org/

The Clearwater Beach Chalk Art Festival arrives in October, on the beach promenade. More than two dozen artists participate, creating original 2- and 3-D paintings for passersby. Donations help support scholarships for visual arts students.

On the east coast, Lake Worth, Melbourne and Vero Beach all boast chalk art fests.

The Annual Lake Worth Street Painting Festival in late February lays claim to being “the country’s largest” – in square footage, at least. It brings in hundreds of artists to create more than 200 pavement paintings in a variety of styles. It’s a two-day event “covering more area than any other festival of its kind in the U.S.,” according to the festival’s website. 

Melbourne invites chalk artists to show off their street-painting skills at the ArtWorks of Eau Gallie Fine Arts Festival in November. It’s a perfect fit for this "working artist" festival, which insists that participants in any medium create works or demonstrate their techniques as they exhibit.

The Hibiscus Festival in Vero Beach puts on its Inaugural Professional Chalk Art Show in April, bringing in internationally recognized street painters to create 2- and 3-D works.

Chalk Festivals in Central Florida

Central Florida is home to two new chalk art festivals: Winter Park’s Chalk the Walk and Sanford’s Chalk Art on the Avenues.

Chalk the Walk, held in November, attracted more than 150 artists to the sidewalks of the city’s first festival Central Park. 

Sanford calls on artists to compete for cash prizes in the city’s historic downtown festival in May. It’s a working artists festival, too, so street painters are – ahem! – right up its alley. 

North Florida hosts Paseo Pastel in St. Augustine in May and the Palatka Chalk Explosion in April. The Palatka event is in its third year in 2015, and includes live music, crafts, food and drink. The theme is “Visions of Well-being.” 

St. Augustine’s Paseo Pastel includes more than 60 artists competing for cash and prizes. 

And, at the southernmost end of the state, Key West hosts its annual Chalkfest in November. Held on the promenade at the Truman Waterfront, it attracts artists from around the world. The international lineup in 2014 brought talent from Holland, Italy, Russia, and from across the United States. The five-day event lands in the cool weather of mid-November, and includes arts and crafts, a chalking area for kids, and a 3-D chalking competition.