Tuesday, April 21, 2026

Side Car Santa Returns to Spread Christmas Spirit in Williamsburg

Santa and Mrs. Santa will once again return to their spot in Merchants Square to hand out toys to all kids. (Side Car Santa)

WILLIAMSBURG — Santa will officially kick off the Christmas season as he returns on his sidecar motorcycle to once again bring toys to all the kids in Merchants Square.

On Saturdays and Sundays until Dec. 21, Side Car Santa will be located in the area of The Cheese Shop and Duke of Gloucester Street and begin delivering toys to the good boys and girls who see him.

Greg Selby, who started the Side Car Santa initiative in 2011 after purchasing a red motorcycle, originally drove around and waved at passersby as Santa.

A friend recommended that, as Santa, he should hand something out to those who approach him.

“Someone suggested that I should pass out candy, and I just felt wrong doing that since I’m not associated with any groups or anything. I didn’t want to be a stranger passing out candy to kids and have a parent have to tell their child that they couldn’t eat it because they don’t trust Santa,” Selby explained.

Selby’s wife, an avid Beanie Baby collector, offered up her collection as a potential item for Santa to hand out. As people learned about the initiative, he has started receiving Beanie Baby donations — or stuffed animals of that size — from across the country. One year, he received a donation of 5,000 Beanie Babies from a former toy seller.

Selby handing out toys in Merchants Square. (Side Car Santa)

“People collected these things so much in the ’80s and ’90s and then they realized they aren’t worth anything, so they gave them to me. I might be the face of this, but this would not work without the support of the community. I couldn’t do this without the people who so generously give. I have people say, ‘Oh I’m sorry, I only have five Beanie Babies,’ and I always tell them, these five toys will make for five happy children when they see Santa,” Selby shared.

Having been Side Car Santa for 14 years, Selby says many folks have made visiting him in Merchants Square a part of their family holiday traditions.

“I have one family that comes down from Richmond, and they’ve come down for 13 years now. They get their picture taken with me every year. All the kids dress up, and they have their family holiday picture taken with me,” Selby said.

Once the Christmas season ends, Selby begins planning for the next year’s holiday season. There is a local year-round drop-off location at Catalillie’s Play Cafe. Selby has also started an Amazon Wish List for toys to be sent directly to him.

No money is involved to participate and no strings are attached to the toys he hands out. Selby says this annual tradition simply brings him joy.

“It makes my Christmas. I look forward to it every single year. I live for Side Car Santa. Christmas would not be the same without doing this … it makes my year,” Selby said.

Side Car Santa will be in Merchants Square on Saturdays beginning around 10 a.m. and Sundays around 11 a.m. He will stay in his location until he runs out of toys.

To learn more, visit Side Car Santa on Facebook.

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