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Greg Selby started “helping Santa” while working for the U.S. Coast Guard on the Eastern Shore of Virginia, making calls to kids who’d written to Santa. He dressed up as Santa for events and thought it was a fun way to get into the holiday spirit.
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Sidecar Santa isn't selling anything and isn't asking for donations. He just wants to spread joy.
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Sidecar Santa says, "...when you give kids a toy, no strings attached, you can see joy in their faces.
If you’ve ever looked into the next lane in traffic only to find yourself staring at who you thought was Santa Claus—on a motorcycle, no less—chances are it made you smile. Even if just for a moment.
And chances are even better that if Greg Selby caught you in that smile he’d smile to himself just the same. After all, that’s his goal—to bring smiles to people’s faces all across Williamsburg as Sidecar Santa.
The Birth of Sidecar Santa
Selby started “helping Santa” while working for the U.S. Coast Guard on the Eastern Shore of Virginia, making calls to kids who’d written to Santa. He dressed up as Santa for events and thought it was a fun way to get into the holiday spirit.
After he retired, in 2011, he bought a red motorcycle.
When December rolled around, he’d decorate his motorcycle and dress up as Santa. It attracted a lot of attention, especially from the kids. But he had nothing to give to the children who came to talk to him.
“People told me to give out candy canes, but I didn’t want to put parents in the position of having to say no to their kids about taking candy from someone they didn’t know,” Selby says.
So he did something else.
“My wife had a bunch of Beanie Babies, because she collected them like everyone did in the 1990s, and so I put them in the sidecar and we handed those out,” he says.
Turns out, “you can fit a lot of Beanie Babies in the sidecar—about 300,” Selby says.
Sidecar Santa in Williamsburg
This year, on weekends between Thanksgiving and Christmas, you’ll find Sidecar Santa and his elf (usually his wife or one of his two daughters) on Duke of Gloucester Street. This is Sidecar Santa’s fifth season spreading cheer in Williamsburg.
“Santa’s a busy guy—he needs a lot of helpers,” Selby says, adding that he takes his role very seriously.
“Once you put on the suit, you become the big guy—don’t break character. The suit to me represents the Christmas spirit.”
Selby doesn’t do it for money, he doesn’t do it for fame—he does it because he is trying to combat cynicism.
“I’m not selling anything. I’m not preaching. I’m not asking for donations. I just want to spread joy, and when you give kids a toy, no strings attached, you can see joy in their faces.”
Last year, Sidecar Santa gave away 3,500 Beanie Babies.
So where did they all come from?
Selby says that he puts a request in the local newspaper and usually meets up with people around town to pick them up. The more people hear about his project, the more Beanie Babies find their way to him.
“Last year, an older gentleman was looking for me up and down the street with a big plastic bag full of them, and I’ve gotten as few as six, and as many as 400 at a time. I check to make sure they are clean and in good condition,” he says.
It can be hard to catch Sidecar Santa, but he’s usually out on the west end of Duke of Gloucester Street on Saturdays and Sundays between Thanksgiving and Christmas in the morning, sometimes until early afternoon.
He’s had his photo taken hundreds of times—and he’s always smiling.
If you'd like to donate Beanie Babies to Sidecar Santa, you can contact him at sidecarsanta@hotmail.com.
