In the early days of Transcona's development, Regent Avenue quickly became the main retail section of the Town(although in the early years, Pandora Avenue was the community's main road into and out of town). But for many years, Regent Avenue, and for that matter all other Transcona streets, was
little more than a wide strip of dirt. In the spring and fall, early or late winter or even after a good rain, these strips of dirt became mud and made travel next to impossible. It was not as serious in the early years when transportation by rail was preferred. However, with the rising popularity of the automobile, the lack of proper roads became an important issue.
The dirt and mud became a symbol for many in Transcona, a symbol that the Town had not quite arrived. While citizens were proud of their water, sewer and power systems, their service sector and of course, their manufacturing plants, the mud streets, ditches and lack of sidewalks was of great concern. Town councilors were constantly being asked to allocate funds for sidewalks for blocks in both the retail and residential districts. The stories of getting stuck in the mud while taking a bus to or from Winnipeg may seem unbelievable today, but it was all too real to the people of Transcona and something that had to be corrected.
An early attempt to bring electric streetcar service from Winnipeg to Transcona met with failure as well. John H. Kern, an early Transcona real estate investor living in Moose Jaw, Saskatchewan, signed an agreement with town council in 1914 to build and operate the system. The Winnipeg Electric Railway Company, which had also been in negotiations with council, made a counter proposal. Kern began laying ties on the route in the summer of 1914 but construction stalled there and no further action was ever taken to supply streetcar service to Transcona.
Gravelling of Regent Avenue and other important traffic arteries occurred sporadically, but the annual activity proved to be an expensive proposition. Finally, in the early 1930's, as part of the program to supply work for the unemployed during the Great Depression, Regent Avenue was paved from Oxford Street (present-day Day Street) to Panet Road (then the boundary of Transcona). The new road, which cost $135,000 was opened officially on July 9, 1931 by Transcona Mayor W. Haigh and the Hon. W.R. Clubb, Minister of Public Works.
The paving was seen as a salvation by many local people, ties with Winnipeg and other major centres were immediately improved, as was the all-important image and first impression of Transcona to visitors. The work, which was accomplished mainly by hand, included a widening of Regent Avenue for the blocks east and west of Bond Street. It was decided to allow parking in the centre lane, which had been covered with asphalt rather than cemented. Because of its dark colour, the two-block section became know as "The Devil Strip."
(Taken from the Transcona Heritage Resources Inventory)
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