I am looking for anything of that sort -- books, posters, newspaper articles, well-written blog posts.
You can probably find most of the HOPL papers online as well as recordings of talks from the later conferences. There's a lot of material! Personally, I really liked "A History of Haskell: Being Lazy with Class", partly because I like Haskell and partly because Simon Peyton Jones is such an engaging speaker.
: paper: http://haskell.cs.yale.edu/wp-content/uploads/2011/02/histor...
: recorded talk: https://www.youtube.com/watch?v=3bjXGrycMhQ
They are also on YouTube:
Panel on Runtime: Richard Kelsey, David Moon, Tucker Withington, Kim Barrett, Scott McKay 
Panel on Compilation: David Detlefs, Will Clinger, Martin Rinard, and Mat Hostetter 
Panel on Language Design: Paul Graham, John Maeda, Jonathan Rees, Guy Steele 
A History of Haskell 
The Early History of Smalltalk 
HOPL III is here: http://dl.acm.org/citation.cfm?id=1238844&coll=DL&dl=GUIDE&C...
HOPL I is here: http://dl.acm.org/citation.cfm?id=800025&coll=DL&dl=GUIDE&CF...
I have the hardcopy versions of I and II that I bought used from Amazon and they're great.
The Evolution of Lisp (Steele and Gabriel):
The Original 'Lambda Papers' by Guy Steele and Gerald Sussman
Many papers on the evolution, design, and implementation of Scheme:
It gives a great overview of the different generations of programming and the significant languages in each.
Also try the Internet Archive (archive.org). It has a lot of "Programming History" stuff, but finding it can be painful:
There are several old primary resources on C's predecessor, B . Structured programming was newish, so it's fun to read these descriptions of newfangled "while" loops.
I owe 90% of every programming thought that entered my mind to the people that contributed to this: