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Amy Grief's history of Halloween on Church Street at blogTO does a great job of explaining how Church and Wellesley became a nexus of Halloween revelry.
Church Street has become Toronto's unofficial Halloween destination. Every year, it transforms into a pedestrian-only boulevard packed with people in outrageous and inventive costumes. It's a party, regardless of the weather and what day Halloween lands on. Work night? Who cares!
But how did this party get started? "It's one of the events in the City of Toronto that needs very little advertising, but gets numbers of people regardless of it's cold, or wet, or anything like that," says Christopher Hudspeth from the Church Wellesley Village BIA.
He says the tradition dates back to the 1960s and 70s. Back then, Halloween gave men a chance to dress in drag - it wasn't really legal any other day of the year.
Bars on Yonge, like the Parkside Tavern and the St. Charles Tavern, held Halloween balls, and many would come gawk at those attending, writes Jamie Bradburn for Torontoist. In the late 1970s, the crowds turned vicious, mocking, jeering and even throwing eggs at those dressed up.
By the early 1980s, things quieted down on Halloween night, and as bars moved to Church Street, so did the party.
Dean Odorico, who owns the popular bar Woody's, has watched the annual Halloween festivities grow over the past 27 years. He says Halloween is an important day for the LGBTQ community and that there have been big parties on Church Street for as long as he's been in the neighbourhood.