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. After 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. In 2015, York Pride Fest transformed and became a registered federal not-for-profit organzation.

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 four years, 2007-2010, 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 12.

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, with two more towns plus all Seneca College campuses agreeing to raise the flag in 2010. Two more municipalities agreed to participate in subsequent years with the result that a total of seven municipalities flew the flag in 2013. Every year eight municipalities and our regional government have continued to grant proclamations or official recognition of our pride week.

2013 was a landmark year as our Pride Festival included the first Pride Parade ever to be staged in York Region. The parade, along Yonge Street in Richmond Hill, featured 30 groups, 15 floats and more than 250 participants.