This will be a quick post, but not too long ago I ran across the image below while digging through image databases maintained by the Indiana Historical Society.
This is an image capture from the original photo, and I have zoomed in on only part of the photo in order to feature the brick building (which I will refer to at the W.W. Scott building). The full sized image can be viewed here. I recommend you take a look. The zoom function on the IHS site is very good and reveals quite a bit of detail in the photo outside what is pictured above. Try to take a look at the advertisements on the utility pole in the center of this frame, and what appears to be a man working a garden on the far right side of the photo (not visible in this view).
Anyway, as the title of this post suggests this photo depicts the intersection of 38th and College Ave. The photo is part of IHS's Indianapolis Boulevards and Parks Photographs collections and is dated May 22, 1914. The perspective is looking west, with the State Fair Grounds and the present day Monon Trail being behind the photographer. I'm unsure why there is a railroad crossing sign in the image, since the rail crossing is behind the photographer. Perhaps the crossing sign is for an interurban or trolley line.
In 1914 the brick building on the south west corner of the intersection contained the Shields Grocery Store, and one of several locations for the W.W. Scott drug store. Based on the signage, this particular location seemed to focus on the sale of cigars.
The Shields Grocery operated at 3772 N. College (Indianapolis Star directory page, 1914, below right) for several years, before the location was taken over by another grocery, the Maple Road Grocery. Even that was short lived as that business was advertised for sale in 1924 (Indianapolis Star advertisement, below left). Various other grocers and other businesses have occupied that address since then.
W.W. Scott was a local druggist who owned several dug stores throughout Indianapolis, including near the end of Virginia Ave. in Fountain Square, farther south on College Ave. and the location at Maple (later renamed 38th St.) and College, which he opened around 1904. (Indianapolis Star, 6/20/19) Pharmacy was something of a family business as Mr. Scotts brothers also owned drug stores, or worked in his other locations Mr. Scott retired to Pasadena, California in 1918 and passed away 6 months later.
Today, the intersection of 38th and College is a bit more developed, although the W.W. Scott building is still there.
In addition to 38th St. being wider, and not dirt, the Scott building has undergone some changes. You can still see the storefronts once occupied by Shields and the drugstore, and the three tiered brick trim at the top of the building. At some point an expansion was built on the west side of the structure (which also added a window), and the middle, second story window on the east side was expanded. A fire escape was added, as was the billboard. Notably, the steel beam set between the first and second stories on the east side is clearly visible today as it was in 1914. The brick wall on the north facing side of the building has been mostly replaced by windows.
Sources:
Indiana Historical Society, Digital Images, http://images.indianahistory.org/cdm
Indianapolis Star, dates noted above.