1885:
Location of corner where Family Market at Wabash and Randolph is now.
There was a barber in the basement on that corner as early as 1885. It was there until '62 or '72.
The yellow "518" would appear to be the steps going down to the barber shop.
Looks like a newspaper at 105 on Randolph.
At 108 Randolph is the first I have heard of a land office in Howard.
At the top under the opera house is a bank that moved to where the old bank is now at Washington and Wabash. I am thinking the bank on the corner moved directly across the street on Randolph where Howard State Bank is now.
I guess if you might have owned a car in 1885, you could go into the alley and fill up, chuckle.
(http://i941.photobucket.com/albums/ad256/waldoegray/Batsons_zpsaee35152.png) (http://s941.photobucket.com/user/waldoegray/media/Batsons_zpsaee35152.png.html)