I found these today in a box of other prints at an antique shop in Havre de Grace, Maryland. From the residue on the one print, it looks like they were originally from a sign company, mocking up billboards. It’s at the same time unfortunate, and extremely exciting to me that despite years of research, both archival and out on the road, these two locations are both unfamiliar to me.
There’s just enough context in them that it seems like one of you out there will be able to ID them.
The sign on the building to the left reads, “Joker’s Inn”, and it looks like the building to the left of that is a cleaners. The quality of the picture is just iffy enough that I can’t make out the street sign. It looks like a numbered street, though. The shot’s late 1960s.
EDIT: This Little Tavern has been ID’ed as Washington No. 26, Good Hope Road.
Another one, also late ’60s, with a partial LT. With the bridge and the stacks, I would think this one would be easier to ID.
Diner Hunter 
Jeez, you are amazing!!!!
Got incredibly lucky with these. Got into the store just as they were closing, and the box had just come in. Took 20 minutes to convince them to sell them to me. Any thoughts on them, Scott? Look like Baltimore to you?
Hello , if you ever go through Spencer ,Iowa please stop at Weasey’s Lounge on Grand Ave. , it opened in 1950 thereabout, by the Clarence Conlon family ,just as a hometown bar but has evolved into a terrific restaurant /bar enjoyed by all . I personally worked there before and after school as janitor until business was sold in 1952 . Y.T. Gary Conlon
I’ll be in Iowa in about another week and a half. If I’m anywhere near, I’ll make a detour. Hard to pass up a tip like that, and hard to pass up visiting another town with the same name as me.