Bolland, who grew up in the Toronto neighbourhood of Mimico, brought the cup to a children's hospital in London, Ont. earlier in the day before landing at a local hockey arena to greet fans.
Bolland scored the winning goal in Game 6 of the Stanley Cup final to win the Cup for the Chicago Blackhawks.
He addressed the crowd and thanked all those in attendance, adding that it was sad leaving Chicago but that he is happy to be a Maple Leaf and is looking forward to "having some fun with the cup."
Each Stanley Cup winning teammate get 24 hours with the cup, and Bolland previously brought the Cup to the west-end neighbourhood in 2010 when the Blackhawks last won the championship.
Attendance was definitely up from 2010 though, as police estimated about 3,000 people came out for the parade. Fans wore both Chicago Blackhawks colours and Toronto Maple Leafs jerseys, and some screamed at Bolland to bring the cup back the "same time next year."
Bolland joked that the Cup was a bit heavy as he repeatedly hoisted it over his head, adding that he hoped to bring the Cup back to Toronto as a Leaf in the future.
Bolland said he also planned to bring the Cup to a famous local watering hole Thursday night called "The Blue Goose," where fans eagerly awaited a chance to see the coveted trophy and the Mimico native up close.
Toronto Mayor Rob Ford was also in attendance with his brother Coun. Doug Ford, and said the day was great for the morale of Leaf fans, calling Toronto a "hockey city."
"It's huge, it's huge. Bolland's a tough guy and that's what we need. He's great on the Leafs. We'll bring it back, we'll bring it back," Ford said.
"We came close this year. We could almost knock off Boston and look how far Boston went. I think we can take it this year for sure."
Superstitions became apparent when Coun. Mark Grimes, who organized the event, chastized the mayor for putting his hands on the Cup, to which Ford replied "come on, come on," in apparent disbelief.
Bolland, whose goal came with just under a minute left in the decisive game, wore a blue T-shirt instead of a Leafs jersey while riding atop an antique fire truck as a bagpipe procession led the parade.