Down on the Corner : Street Artist Chester Rogers returns to his roost ‘in the roots’


In the dog days of summer, any bit of shade one can find along the sidewalks of Estero Boulevard is a godsend. On the north side of the street, in the northwest corner of the iconic Surf Club property near the center of town, you will find one such oasis – a tree whose gnarly roots grab the ground in a tangle while stalwartly holding up the trunk and branches. With then owner Bruce Cermak’s permission and blessing, popular local artist Chester Rogers could be found these last few years happily sheltered in the dappled shade of that tree – chair, easel, art supplies arrayed around him – offering free caricatures to people passing by. That is until the neighborhood bar and grill changed hands a few years ago.

When the Surf Club changed hands, didn’t reopen, and then construction got underway, Chester was forced to relocate. “I went back to the Dairy Queen (in Times Square),” he explains as he set up under the Surf Club tree for the first time in over a year last Saturday. “I didn’t see any of the locals there like I used to,” he adds, with a comment that summer and construction has hit the locals harder than the tourists. “They don’t seem to get out and about as much, I think.” But ever the optimist, Rogers adds, “It’ll get better. I can’t wait to see everyone.”

Over time, fourth-generation Floridian and a self-named “Lee County cracker” Rogers has sketched just about every local and visitor who has encountered this prolific and giving man. At every fund and awareness-raising event in town, Chester donates his time and his artwork for auction or raffle, or simply to keep children engaged in art and playful banter while their parents look on appreciatively. One of his favorite days of the year is the Surfers for Autism event that takes place annually at Crescent Beach Park. He gives away beads and other little gifts to all the children who come by his spot, whether they sit for a portrait or engage in a little artwork themselves.

For all he contributes to what is so good about our community, Rogers says making other people happy makes him happy. As he told the Sand Paper in an interview* a few years ago, Chester is glad his art brings so much happiness to people. “But, it’s for me, it really is!”

Chester enjoys support and patronage from many Islanders who are more than happy to contribute art supplies, transportation assistance and references for commissioned work. “I am so blessed,” says Rogers as he hangs beads and bracelets from the branches above, ready for picking. “The new owners (of the Surf Club) called and told me I could set up under my tree again.” He smiles and says with emotion thickening his voice, “I don’t know why I get so much love and support from this community.”

We do, Chester.
Jo List

SAND LIFE Entertainment Magazine, ‘Chester Rogers Street Artist – Beach Tour 2014’ September, 2014