[smokelessjoe]

I even went as far as signing up on a Gun Collectors forum and asked if they could provide any info on the guns. (Hoping for some sort of clue?) They were very helpful but it led down a dead end road.

Interestingly, those guys were intrigued by the (guy with sign) buttoned up pants leg. Debating whether or not a drive chain could be on the left or right side of a motorcycle or bicycle.

One fellow stated the he thought the photo was taken at West Side Park in 1899??? I cannot find any pictures of West Side that match...

You can see his pants leg and the Cycles in the bottom photo.

Here is a photo of the gun!

That appears to be a Stevens Tip Up. Also known as a "pocket rifle".
They had removable shoulder stocks, so they could be used as a rifle or a pistol.