The discussion on the Fort Garry site prompted me to look at this map, a rather whimsical look at the Winnipeg of 1872. Things of note:
-The only sidewalks depicted were on the east side from Main from Notre Dame (Pioneer) to Post Office (Lombard) Streets.
-Aside from the dissapearance of Pelly Street and Thistle Lane, the streets shown are generally as they are today. Even the trail leading from Fort Garry to the Forks roughly follows today's Forks Market Rd. The lane running to the river from the northernmost point of Rorie still exists in part, and was the planned atrium from the ill-fated Nygard Village
-#3 and #4, Drever's building and the Red Salloon at Portage and Main. The map shows a slight bottleneck on Portage at Main. One historical account says that the Salloon and part of Drever's building sat in what are now the east-bound lanes of Portage Ave until the early 1880s
-#47, the "old Ross house" is (besides the north gate of Fort Garry) is the only structure that has survived until today. It was moved twice, and is now a museum in Point Douglas
-It's interesting to think, that if both Pelly Street and Portage both lasted, that the two would have crossed at around Smith and Donald Streets, and Winnipeg would have a similar intersection to Manhattan's Broadway and Seventh Ave, which forms Times Square
(Large version
here)