A recent discussion on ME-LIBS mentioned the puzzlemaker, from Discovery Education. This website automatically generates crossword puzzles (and other types of puzzles, too) from a list of words and clues you enter.
One drawback is that it just generates the puzzle to a webpage, which you're then supposed to print out. A "play online" version would be more fun; also helpful would be a print-friendly pdf version (I had to tweak my Library 2.0 Crossword in Word before printing to pdf).
While looking for one with more output options, I found that there seems to be a lot of software to generate puzzles, but only a few are free:
- AmoredPenguin.com (also makes pdf)
- Teach-nology.com (not automatic - you enter the letters where you want them)
- AwesomeClipartForKids.com (not working?)
This could be used as a fun library program for kids or teens, for staff, for making an activity to go along with a book display, for local history/events/landmarks, or even for a book display on crosswords (incidentally, the first crossword puzzle was complied by Arthur Wynne and appeared in the New York World on Dec. 21st, 1913).