January 26, 2026
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A Cadillac for the Community: Ron Munday’s Chalkboard Ride Builds Relationships

Ron Munday and his Chalk Caddy

Port Charlotte’s got a new local legend, and his name is Ron Munday. He rolled into town from Arizona and didn’t know a soul, so he did something bold: he turned his old Cadillac into a gigantic chalkboard. Now, anyone can sign it, scribble a drawing, or just leave their mark.

It’s totally legal in Florida, by the way. Just keep the chalk away from the license plate, windows, and headlights. No one wants to get in trouble over doodles.

A creative way to make new friends in the community

These days, everyone recognizes Ron’s car. A year ago, Ron was a stranger. Now he can’t walk down the street without someone calling out, “Hey, what’s up, chalk daddy?” Even a cop once pulled him over just to sign his car.

The Cadillac, now affectionately called the Chalk Caddy, has signatures from all over: strangers, firefighters, business owners, even folks from Waffle House. Ron lets people draw whatever they want, as long as it’s not offensive. He keeps a black marker handy, just in case someone gets out of line.

The whole thing started by accident. Ron was shopping for oil at Walmart, spotted some spray-on chalkboard paint and acrylic markers, and something clicked. Six hours later, chalkboard paint covered his car. He’s currently on coat number two and estimates he’s collected around 1,800 messages on his Chalk Caddy.

When the car fills up with signatures and drawings, Ron just paints over it and starts again. For Ron, it’s simple: he just wants to live his life and meet people.

And his advice for anyone struggling to make friends? “Be yourself. Just have fun.”

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