Annual pride celebrations have been staged in York Region since 2001. For the first five years, they were hosted by individual, volunteer-based organizations, but those groups had ceased their operations by the end of 2005 resulting in the lack of any pride week events during the following year.

Subsequently, York Pride Fest was launched in February 2007 by the York Region LGBT Community Outreach Project, a four-year Trillium funded initiative to develop and support the delivery of services to meet the needs of LGBT persons and their families in York Region. Since that time, York Pride Fest has operated as a coalition of local LGBT-relevant service providers and community volunteers, working together to organize and progressively expand the region's annual pride festival.

Each year, pride week celebrations organized by York Pride Fest have included proclamation/recognition requests to local government bodies, LGBT awareness displays presented at libraries across the region, as well as a number of hosted events. Over the first three years, 2007-2009, the number of annual pride events was increased from 3 to 7, overall event attendance tripled and the number of awareness display venues was increased from 6 to 10. Starting in 2008, York Pride Fest commenced participation in Toronto's annual pride parade in order to represent and enhance the visibility of York Region's LGBT community. The following year, for the first time, rainbow flags were flown throughout pride week by three of the region's municipalities ,whilst eight municipalities and regional government continued to grant proclamations or official recognition of our pride week.