Organizer Randy Young with Friends of Veterans Canada says about 30 vehicles bearing Canadian flags made up the convoy, with small crowds of people at times clustered along highways or on overpasses to cheer them on.
Young says that though the number of donations were less than he'd hoped for, he's optimistic his charity will hit its goal of $100,000 by Christmas Eve.
The donations from the Vincent-Cirillo "salute rally" will be given to kids living on military bases as a show of thanks for hardships such as changing schools and losing friends when their parents are transferred.
Young says the toys, including those bought with the money, are to be given out as Christmas presents addressed from Cirillo and Vincent, who were killed in separate incidents last month.
The ride started at CFB Trenton east of Toronto and headed to a Royal Canadian Legion branch in Hamilton.
"We want this to be a celebration of Vincent and Cirillo's life," he said by phone while travelling on a highway west of Toronto.
"It's kind of like an Irish wake without the booze. We're proud of our soldiers and want to the world to know it."
Young said his group's second annual rally and toy drive aims to send a message of thanks to the youngsters — who feel the at-home stress of military life but get little recognition for the difficulties they can face.
"These military kids deserve it. They don't ask for nothing, they move around this country, they move around the world, what do they ask from us? Nothing," he said.
"This about us as Canadians saying thank you to them."
Cirillo was gunned down while standing guard at the National War Memorial. His assailant was later killed during a gunfight on nearby Parliament Hill. Vincent was run over near Montreal in what police have said was a deliberate act by someone with jihadist sympathies.