These sleighs are cabs parked on the stand at the corner of Portage and Main, circa 1885.
The cab bylaw allowed licence plates to be transferred from carriages to sleighs, but it is possible that these sleighs are carriages with their wheels temporarily replaced by runners. There doesn't seem to have been much advantage to runners. In later years, wheeled carriages were used in both summer and winter.
Portage and Main, the centre of Winnipeg's business district, was the most lucrative place for cabs to hang out and the first cab stands were established here. In the absence of street paving the City of Winnipeg constructed wooden platforms for the cabs to park on, so that horses did not have to stand in mud and water for long periods.
Local merchants did not like having large numbers of cabs congregating outside their establishments. They took up space needed for deliveries and customer parking, and the drivers liked to loiter on the sidewalk, socializing among themselves and making rude remarks about anyone who passed by.
During the 1880's, the "official" Portage Avenue cab stand was moved several times, but the cabbies generally ignored each new stand bylaw. Complaints from the business community would spark heightened enforcement by the police, but the cabs would eventually drift back to Portage and Main and everything would return to normal.
Picture source: Provincial Archives of Manitoba, Transportation -- Sleigh, 3.
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Revised February 13, 1998