In this post, there is an example of such a prompt. It displays information, when you enter specified working directory.
The picture below shows my configuration:
This is achieved with setting a variable PROMPT_COMMAND which is evaluated every time you run a command. In my case, there is a condition, which looks for matching path.
# dynamic PS prompt export PROMPT_COMMAND='PS1="$(if [ "$(pwd | grep /mnt/storage/backup_git)" ]; then echo "\\[\\033[32m\\]backup_git "; fi;)\[\033[01;31m\]\h\[\033[01;34m\] \W \$\[\033[00m\] "'