The Smile Squad: Bike-riding women ‘peddling’ good feelings

Lance Shearer

The ladies all played pickleball together. Then, all of a sudden, they couldn’t.

So, to keep up their fitness and use up the time not spent on the court after the Racquet Center closed, a group of women determined to get on their bicycles and ride. And the Smile Squad was born.

“We decided to go visit all our pickleball friends, and it sort of grew from there,” said Jeannie Wagner. Along with Eve Stoebel, Anne DePalma, and Janet Moses, Wagner is part of the “core four,” as they call themselves, who meet up daily on their bikes, sporting American flags, butterfly wings (“a new addition from the Dollar Store”), bubble blowers and silly songs, riding the island to spread good cheer.

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“Being on lockdown, people want cheering up. We’ve been doing it for five weeks total now,” said Wagner. On Saturday morning, their first stop after meeting by the YMCA sign on San Marco was at the newly reopened Racquet Center, where they were greeted with cheers and waves.

Joined by “guest riders,” the Smile Squad now gets requests for “bike-bys” friends, friends of friends, and residents at large. The group saddles up and delivers their unique brand of pep rally spirit.

“We’re the Smile Squad, here to bring you cheer. We hope you’re glad that we are here,” they chanted, to the amusement and delight of residents at the Seawatch condominium. “We bike the miles to bring you smiles.”

Another chant brought memories of high school cheerleaders. “S – M – I – L – E – Smile Squad is what we be!” The group doesn’t have any paid lyricists; their songs, said Moses, are often composed while biking the island’s streets.

Wagner said they do “safe distance bike-bys,” but the group doesn’t wear masks, and in their routines, they crowd within what the CDC would recommend for optimum social distance.

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The squad made additional stops that morning at Sunset House and Smokehouse Harbor, as well as impromptu encounters along the street. At every stop, the group makes their mark, writing “Smile Squad” in chalk on the sidewalk, and adding a smiley face so you know they mean it. The group also takes requests for special birthday and anniversary greetings.

Trish Rowland was impressed enough when the Smile Squad stopped and entertained at her condo that she made a video from her balcony and posted it to Facebook. Wagner also shoots copious selfies and shots of each stop to post online, so the group’s activities are well-documented.

In the time of social distancing, social media helps these very social riders get their message out. This Marco Island equivalent of Hell’s Angels figures they have cycled up and down all of Marco’s 146 miles of streets. They gave no indication of being ready to hang up their wings, but hey – the pickleball courts have opened back up.

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