Bike to Work Day began in 2007 when a group of cyclists hosted an event to raise the profile of cycling in Winnipeg, to encourage people to cycle to work, and to advocate for better cycling infrastructure. This became a yearly event and in 2011, other organizations were invited to host pit-stops, further raising its profile and accessibility. The yearly event was overseen by a steering committee, and it became so successful that in 2014, Bike to Work Day was expanded to become Bike Week, which celebrated and promoted cycling more broadly, rather than focusing specifically on commuting.

Bike Week Winnipeg was born out of Bike to Work Day, which first took place in 2007. Bike to Work Day was hugely successful and in 2014, it was expanded into Bike Week, which sought to promote not just commuting, but all aspects of cycling in Winnipeg. Bike Week Winnipeg was officially incorporated in 2017 and its board provides direction to an events contractor and a volunteer planning committee.